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Artykuły w czasopismach na temat „Γ Amino Acid”

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Data publikacji: 6 września 2023

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1

Hettasch, Joann M., Mark G. Bolyard i Susan T. Lord. "The Residues AGDV of Recombinant γ Chains of Human Fibrinogen Must Be Carboxy-Terminal to Support Human Platelet Aggregation". Thrombosis and Haemostasis 68, nr 06 (1992): 701–6. http://dx.doi.org/10.1055/s-0038-1646347.

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SummaryThe carboxy-terminus of the γ chain of fibrinogen contains a sequence which is believed to be one of the domains that interacts with glycoprotein (GP) IIb/IIIa to support platelet aggregation. A normal variant of fibrinogen exists in which the four carboxy-terminal amino acids are replaced by 20 amino acids. This variant, known as γ’, has been reported to bind less effectively to platelets. The purpose of the present study was to engineer novel proteins to determine what differences in amino acid sequence between the γ and γ’ chains influence the interaction of the carboxyterminus with GPIIb/IIIa. In this regard, the γ chain cDNA in a bacterial plasmid expression vector was modified by oligonucleotide-directed mutagenesis to produce recombinant γ chains with amino acid changes in the carboxy-terminus which reflect the differences between γ and γ’. The recombinant γ chain with an unmodified carboxy-terminus supported adenosine diphosphate (ADP)-induced platelet aggregation to the same extent as intact fibrinogen. In contrast, the ability of γ’ 427 (the recombinant γ’ variant) and γ 427 (where the 16 amino acid γ’ extension [412–427] was added to the carboxy-terminus of γ) to support platelet aggregation was markedly reduced. In addition, the extent of ADP-induced platelet aggregation was decreased in the presence of γ’ 411 (where amino acids 408–411 in γ were replaced with amino acids 408–411 in γ’), while γ 407 (where the four carboxy-terminal amino acids were deleted) was not capable of supporting aggregation. These findings demonstrate that the four residues AGDV are not only required but must be carboxy-terminal to support platelet aggregation.

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2

Valachová, Dominika, Branislav Ferko, Eva Puchľová, Oľga Caletková, Dušan Berkeš, Andrej Kolarovič i Pavol Jakubec. "Stereoselective Synthesis of syn-γ-Hydroxynorvaline and Related α-Amino Acids". Synthesis 51, nr 24 (16.10.2019): 4568–75. http://dx.doi.org/10.1055/s-0039-1690705.

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The total syntheses of three enantiomerically pure non-proteinogenic amino acids, l-norvaline, γ-oxonorvaline, and syn-γ-hydroxynorvaline, are reported. The chromatography-free route pivoted on the construction of highly enantiomerically enriched substituted α-amino-γ-oxopentanoic acid, from which all three members were accessed divergently via chemoselective and stereoselective reductions. The rapid synthesis of this key α-amino-γ-oxopentanoic acid was achieved by a highly diastereoselective crystallisation-driven three-component Mannich reaction from the readily available building blocks acetone, glyoxylic acid monohydrate, and (S)-(4-methoxyphenyl)ethylamine. The enantiomeric purity of all target molecules was confirmed by HPLC analysis, either of the amino acids or their derivatives.

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3

Dutta, Arpita, Suven Das, Purak Das, Suvendu Maity, Prasanta Ghosh i Soumya Shankha Biswas. "Unique supramolecular assembly of a synthetic achiral α, γ-hybrid tripeptide". Zeitschrift für Kristallographie - Crystalline Materials 237, nr 1-3 (1.03.2022): 77–81. http://dx.doi.org/10.1515/zkri-2022-0002.

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Abstract An achiral tripeptide, namely, Boc-γ-Abu-m-ABA-Aib-OMe (γ-Abu: γ−amino butyric acid; m-ABA: meta-aminobenzoic acid) was synthesized by solution phase procedure. The α, γ-hybrid peptide was designed in such a way that two dissimilar γ−amino acids, one flexible and another rigid, were positioned sidewise along with α-amino isobutyric acid (Aib) as C-terminal residue. The single crystal X-ray diffraction analysis revealed that two kinks were generated around centrally placed m-ABA. Interestingly, the peptide self-assembled via three intermolecular N–H···O and one intermolecular C–H···O hydrogen bonding interactions to supramlecular helical architecture.

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4

Кудрявский, Дмитрий Леонович, Елена Константиновна Фомина, Людмила Юльевна Тычинская, Евгений Доминикович Скаковский i Светлана Евгеньевна Богушевич. "NMR spectroscopy of Cu(II) complexes with acrylamide and sodium acrylate copolymer and ω-amino acids". Journal of the Belarusian State University. Chemistry, nr 1 (12.04.2021): 85–98. http://dx.doi.org/10.33581/2520-257x-2021-1-85-98.

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Macromolecular complexes of acrylamide and sodium acrylate copolymer with microelements, including Cu(II), may form at preparation of crop protection and stimulation compositions, where the copolymer serves as an adhesive, water-retaining and film-forming agent. Preparations for crop production may also contain amino acids that protect plants under stressful conditions (cold, dry, etc.). Carboxylic groups of copolymer, carboxylic and amino groups of amino acids may be involved in mixed Cu(II) ions complexes formation. Number of methylene groups separating carboxylic and amino group of amino acids affects its ability to form a stable chelate cycle and, therefore, ligand composition of mixed Cu(II) ions complexes with acrylamide and sodium acrylate copolymer and amino acid. This work is aimed at determining the ligand composition of mixed macromolecular Cu(II) ion complexes with acrylamide and sodium acrylate copolymer and ω-amino acids (β-alanine, γ-aminobutyric acid, ε-aminocaproic acid). 13C and 1H NMR spectroscopy was used to clarify complexes composition. A complex where carboxylic groups of amino acids are ligands has been found to form in aqueous solutions of Cu(II) ions and ω-amino acid (β-alanine, γ-aminobutyric acid, ε-aminocaproic acid) at molar ratio of Cu(II) ions – amino acid equal to 1 : 6. A chelate complex where both carboxylic and amino groups of β-alanine are involved in coordination has been discovered to form in the solution containing Cu(II) ions, β-alanine, as well as acrylamide and sodium acrylate copolymer at molar ratio of Cu(II) – β-alanine – copolymer COO− equal to 1 : 6 : 30. Carboxylic groups of copolymer participate in complex formation as well. Carboxylic groups of both amino acids and the copolymer have been shown to participate in complex formation in aqueous solutions containing Cu(II) ions, either γ-aminobutyric or ε-aminokaproic acid and also acrylamide and sodium acrylate copolymer.

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5

Speranza, Giovanna, Marco Rabuffetti, Nikolina Vidović i Carlo F. Morelli. "Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure". Molbank 2020, nr 3 (10.07.2020): M1147. http://dx.doi.org/10.3390/m1147.

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γ-Glutamyl derivatives of sulfur amino acids have been prepared in multigram scale starting from readily available starting materials. The synthesis comprises two one-pot operations, both consisting of two reactions. In the first operation, N-phtaloyl-l-glutamic acid anhydride is obtained from l-glutamic acid and phtalic anhydride. In the second one, N-phtaloyl-l-glutamic acid anhydride is used to acylate amino acids and the N-phtaloyl protecting group is removed. The described approach offers a viable entry to γ-glutamyl derivatives of sulfur-containing amino acids with flavor-enhancer and nutraceutical properties.

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6

Čeřovský, Václav, i Karel Jošt. "Enzymatically catalyzed synthesis of dipeptides of γ-carboxy-L-glutamic acid from benzyloxycarbonyl-γ-carboxy-DL-glutamic acid". Collection of Czechoslovak Chemical Communications 50, nr 4 (1985): 878–84. http://dx.doi.org/10.1135/cccc19850878.

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Enantioselective reaction of benzyloxycarbonyl-γ-carboxy-DL-glutamic acid with phenylhydrazides of various amino acids and with leucine, protected with various carboxy-protecting groups, has been studied.

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7

Zhu, Shaozhou, Cuiyu Gong, Dawei Song, Shuaihua Gao i Guojun Zheng. "Discovery of a Novel (+)-γ-Lactamase from Bradyrhizobium japonicum USDA 6 by Rational Genome Mining". Applied and Environmental Microbiology 78, nr 20 (10.08.2012): 7492–95. http://dx.doi.org/10.1128/aem.01398-12.

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ABSTRACTA novel (+)-γ-lactamase used for the resolution of racemic γ-lactam fromBradyrhizobium japonicumUSDA 6 was found as a result of sequence-structure guided genome mining. It consists of 409 amino acids, only 49% of which are identical to the amino acid sequences of the known (+)-γ-lactamase fromSulfolobus solfataricus. This is only the third (+)-γ-lactamase gene to be reported.

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8

Pataj, Zoltán, István Ilisz, Anita Aranyi, Enikő Forró, Ferenc Fülöp, Daniel W. Armstrong i Antal Péter. "LC Separation of γ-Amino Acid Enantiomers". Chromatographia 71, S1 (5.02.2010): 13–19. http://dx.doi.org/10.1365/s10337-010-1484-2.

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9

Onozato, Mayu, Kana Kobata, Tatsuya Sakamoto, Hideaki Ichiba i Takeshi Fukushima. "LC–MS/MS Analysis of Thiol-Containing Amino Acids in Exosomal Fraction of Serum". Journal of Chromatographic Science 58, nr 7 (24.06.2020): 636–40. http://dx.doi.org/10.1093/chromsci/bmaa028.

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Abstract It has been suggested that thiol-containing amino acids could be used as biomarkers for diseases associated with oxidative stress. We investigated the thiol-containing amino acids, homocysteine (Hcy), cysteine (Cys), glutathione (GSH) and γ-glutamylcysteine (γ-GluCys), in commercial human serum by using liquid chromatography–tandem mass spectrometry (LC–MS/MS) after precolumn derivatization with 4-fluoro-7-sulfobenzofurazan. This method was applied to determine the composition of thiol-containing amino acids in exosomes prepared from the serum. Hcy, Cys, GSH and γ-GluCys could be detected in the exosomal fraction, and the ratio of each thiol-containing amino acid was similar to those in the corresponding native serum. Cys (94.76%) was most enriched in the exosomal fraction, followed by GSH (2.97%), γ-GluCys (1.59%) and Hcy (0.68%). These findings suggest that thiol-containing amino acids, Hcy, Cys, GSH and γ-GluCys, are included in exosomes in human serum.

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10

Allan, RD, RK Duke, TW Hambley, GAR Johnston, KN Mewett, N. Quickert i HW Tran. "Synthesis of Unsaturated Analogues of Glutamic Acid: Amination of Trianions From Unsaturated Dicarboxylic Acids With Chloramine". Australian Journal of Chemistry 49, nr 7 (1996): 785. http://dx.doi.org/10.1071/ch9960785.

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Trianions can be formed from dicarboxylic acids which contain a β,γ -double bond, and amination with chloramine yields β,γ-unsaturated α-amino acids. This methodology provides a convenient synthesis of amino acids that are inaccessible by other routes. (Z)-3-Phenylthiopent-2-enedioic acid and all four stable unsaturated analogues of the conformationally restricted glutamate analogue 1-aminocyclopentane-1,3-dicarboxylic acid have been synthesized to demonstrate the applicability of the method. The structure of one of the amino acid products, (�)-cis-1-aminocyclopent-4-ene-1,3-dicarboxylic acid (7), has been determined; it crystallizes in the space group P21/c, a 9.245(24), b 8.455(2), c 9.311(3) Ǻ, β 95.00(2)°, and the structure was refined to R 0.035 for 980 F.

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11

Srinivasulu, G., M. H. V. Ramana Rao, S. Kiran Kumar i A. C. Kunwar. "β-Hairpin peptides containing 3-amino benzoic acid, a constrained γ-amino acid". Arkivoc 2004, nr 8 (9.01.2005): 69–86. http://dx.doi.org/10.3998/ark.5550190.0005.810.

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12

Baldwin, Jack E., Mark G. Moloney i Michael North. "Non-proteinogenic amino acid synthesis: Synthesis of β,γ-unsaturated α-amino acids from asparic acid". Tetrahedron 45, nr 19 (styczeń 1989): 6319–30. http://dx.doi.org/10.1016/s0040-4020(01)85141-3.

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13

Campbell, Malcolm M., Arthur J. Floyd, Terry Lewis, Mary F. Mahon i Ronald J. Ogilvie. "β,γ,-Unsaturated α-amino acid δ-lactones; precursors for polyhydroxy amino acids". Tetrahedron Letters 30, nr 15 (styczeń 1989): 1993–96. http://dx.doi.org/10.1016/s0040-4039(00)99633-3.

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14

Capasso, R., P. Pucci, G. Randazzo i A. Malorni. "Fast atom bombardment (FAB) and chemical ionization (CI) mass spectrometry of γ-carboxyglutamic acid, 5-substituted-4,4-dicarboxyprolines, and their monodecarboxy derivatives glutamic acid and 5-substituted-4-carboxyprolines". Canadian Journal of Chemistry 66, nr 9 (1.09.1988): 2177–80. http://dx.doi.org/10.1139/v88-346.

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DL-γ-Carboxyglutamic acid (Gla) reacts easily and quantitatively with aldehydes to give the racemic diastereoisomers of 5-substituted-4,4-dicarboxyprolines. After heating at 100 °C for 30 minutes these amino acids lose a carboxyl group from C-γ of Gla and C-4 of the proline ring to give glutamic acid and the racemic diastereoisomers of cyclic analogs of glutamic acid respectively. This paper reports a study of the above-mentioned compounds by using FAB mass spectrometry in comparison with CI analysis. FAB turned out to be an adequate ionization technique for dealing with such nonvolatile and thermolabile amino acids, and may thus allow the development of a rapid and sensitive method for detecting γ-carboxyglutamic acid in urine and in other biological matrices in pathological cases (i.e., renal stones and blood serum).

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15

Matsumura, Atsushi, Yoshinosuke Usuki i Tetsuya Satoh. "Palladium-Catalyzed sp3 C–H Acetoxylation of α,α-Disubstituted α-Amino Acids". Chemistry 5, nr 2 (1.06.2023): 1369–77. http://dx.doi.org/10.3390/chemistry5020093.

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The sp3 C–H acetoxylation at the β-position of α,α-disubstituted α-amino acids proceeds smoothly under palladium catalysis in the presence of PhI(OAc)2. This reaction provides a straightforward synthetic route to non-natural β-acetoxy-α-amino acids. The reaction of α-aminocyclopropanecarboxylic acid takes place via ring-opening to selectively afford an acyclic γ-acetoxy-α,β-unsaturated amino acid.

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16

Remete, Attila Márió, i Loránd Kiss. "Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs". Molecules 24, nr 1 (3.01.2019): 161. http://dx.doi.org/10.3390/molecules24010161.

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Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of the formed adduct with HC(OMe)3 and nucleophilic displacement of chlorine with various N-nucleophiles in the resulting 6-chloropurine moiety.

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17

Pettit, George R., i Paul S. Nelson. "Synthesis of amino acid diazoketones". Canadian Journal of Chemistry 64, nr 11 (1.11.1986): 2097–102. http://dx.doi.org/10.1139/v86-346.

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A study of carboxylic acid → diazoketone conversion was pursued employing the γ-carboxyl group of otherwise protected L-glutamic acids. The Arndt–Eistert route employing carboxylic acid chloride intermediates was found best (52% yield, 5b), performed at very low temperatures employing oxalyl chloride in dimethylformamide–tetrahydrofuran followed by diazomethane at −23 °C. Alternatively, substitution of a mixed carbonic anhydride for the acyl chloride led to very similar yields (57% of 5b) of diazoketones (5). Among a series of active ester intermediates (7) examined, only the ODnp (7d) and SPfp (7f) esters were found to react (23–26% yield), at least partially, with diazomethane. The latter two reactions appear to represent the first such examples employing active esters.

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18

Jiang, Yang, Ru-Gang Zhong, Bo Tan, Yan-Mei Li i Yu-Fen Zhao. "Recognition of α-Amino Acid from β- and γ-Amino Acid by N -Phosphorylation". Phosphorus, Sulfur, and Silicon and the Related Elements 178, nr 4 (kwiecień 2003): 831–37. http://dx.doi.org/10.1080/10426500307806.

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19

Brodzki, Adam, Piotr Brodzki, Maria Szpetnar i Marcin R. Tatara. "Serum Concentration of Free Amino Acids in Dogs Suffering From Perianal Tumours". Bulletin of the Veterinary Institute in Pulawy 57, nr 1 (1.03.2013): 47–52. http://dx.doi.org/10.2478/bvip-2013-0009.

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Abstract The aim of the study was to determine serum free amino acid concentration in male dogs suffering from benign and malignant perianal tumours. Serum concentrations of cysteic acid, glutamic acid, glutamine, aspartic acid, glycine, γ-aminobutyric acid, tryptophan, methionine, arginine, taurine, threonine, tyrosine, alanine, valine, isoleucine, and leucine were significantly changed in dogs suffering from benign and/or malignant tumours when compared to the control group (P<0.05). Serum concentration of serine, phenylalanine, lysine and histidine was not influenced in dogs with neoplastic disease (P>0.05). The evaluation of serum free amino acid concentration, has shown that threonine, glutamic acid, alanine, valine, isoleucine, leucine, γ-aminobutyric acid, and glycine have the highest diagnostic and prognostic value in dogs suffering from benign and malignant perianal tumours. Highly diagnostic and prognostic value in relation to benign tumour growth was also found while evaluating branched chain and acidic groups of amino acids. Serine, phenylalanine, lysine, and histidine, as well as alkaline amino acids were proved not to have diagnostic and prognostic value in dogs with the tumours. Thus, the evaluation of free amino acid concentration may serve diagnostic purposes and help in tumour malignancy differentiation. The elaborated experimental model may be used in further studies on neoplastic disease development and monitoring of applied treatment efficiency.

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20

Doğan, Fatih, Kevser Temizkan i İsmet Kaya. "Regioselective synthesis of polygamma (γ) acid". RSC Advances 5, nr 66 (2015): 53369–80. http://dx.doi.org/10.1039/c5ra07408h.

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The oxidative polymerization of 6-amino-4-hydroxy-2-naphthalenesulfonic acid was carried out in an aqueous alkaline medium. The polymer showed uncommon multicolored emission behavior in DMSO, emitting blue, green, and yellow light at 405, 480, and 532 nm, respectively.

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21

Haneishi, Ayumi, Kazuyoshi Yamauchi, Fumiko Terasawa, Toshiro Ito, Fumihiro Ishida, Nobuo Okumura i Noriko Fujihara. "A C-terminal amino acid substitution in the γ-chain caused by a novel heterozygous frameshift mutation (Fibrinogen Matsumoto VII) results in hypofibrinogenaemia". Thrombosis and Haemostasis 104, nr 08 (2010): 213–33. http://dx.doi.org/10.1160/th09-08-0540.

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SummaryWe found a novel hypofibrinogenemia designated as Matsumoto VII (M-VII), which is caused by a heterozygous nucleotide deletion at position g.7651 in FGG and a subsequent frameshift mutation in codon 387 of the γ-chain. This frameshift results in 25 amino acid substitutions, late termination of translation with elongation by 15 amino acids, and the introduction of a canonical glycosylation site. Western blot analysis of the patient’s plasma fibrinogen visualised with anti-γ-chain antibody revealed the presence of two extra bands. To identify the extra bands and determine which of the above-mentioned alterations caused the assembly and/or secretion defects in the patient, 11 variant vectors that introduced mutations into the cDNA of the γ-chain or γ′-chain were transfected into Chinese hamster ovary cells. In vitro expression of transfectants containing γΔ7651A and γΔ7651A/399T (γΔ7651A with an amino acid substitution of 399Asn by Thr and a variant lacking the canonical glycosylation site) demonstrated a reduction in secretion to approximately 20% of the level seen in the transfectants carrying the normal γ-chain. Furthermore, results from other transfectants demonstrated that eight aberrant residues between 391 and 398 of the M-VII variant, rather than the 15 amino acid extension or the additional glycosylation, are responsible for the reduced levels of assembly and secretion of M-VII variant fibrinogen. Finally, the results of this study and our previous reports demonstrate that the fibrinogen γ-chain C-terminal tail (388–411) is not necessary for protein assembly or secretion, but the aberrant amino acid sequence observed in the M-VII variant (especially 391–398) disturbs these functions.

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22

Guruprasad, K., S. Shukla, S. Adindla i L. Guruprasad. "Prediction of γ-turns from amino acid sequences". Journal of Peptide Research 61, nr 5 (28.03.2003): 243–51. http://dx.doi.org/10.1034/j.1399-3011.2003.00054.x.

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23

Grib, H. "Amino acid retention with alumina γ nanofiltration membrane". Journal of Membrane Science 172, nr 1-2 (1.07.2000): 9–17. http://dx.doi.org/10.1016/s0376-7388(00)00320-3.

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24

Mouriès, Christine, Brigitte Deguin, Foudil Lamari, Marie-José Foglietti, François Tillequin i Michel Koch. "Homochiral rigid γ-amino acid glycosides from aucubin". Tetrahedron: Asymmetry 14, nr 9 (maj 2003): 1083–86. http://dx.doi.org/10.1016/s0957-4166(03)00020-x.

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25

Wenger, Mazal, i Joel Bernstein. "Designing a Cocrystal of γ-Amino Butyric Acid". Angewandte Chemie 118, nr 47 (4.12.2006): 8134–37. http://dx.doi.org/10.1002/ange.200603241.

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26

Wenger, Mazal, i Joel Bernstein. "Designing a Cocrystal of γ-Amino Butyric Acid". Angewandte Chemie International Edition 45, nr 47 (4.12.2006): 7966–69. http://dx.doi.org/10.1002/anie.200603241.

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Reynolds, J. N., i W. J. Racz. "Effects of methylmercury on the spontaneous and potassium-evoked release of endogenous amino acids from mouse cerebellar slices". Canadian Journal of Physiology and Pharmacology 65, nr 5 (1.05.1987): 791–98. http://dx.doi.org/10.1139/y87-127.

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The effects of methylmercury on the spontaneous and potassium-evoked release of endogenous amino acids from mouse cerebellar slices have been examined. Methylmercury induced a concentration-dependent increase in the spontaneous release of glutamate, aspartate, γ-aminobutyric acid, and taurine from mouse cerebellar slices. Glycine release was slightly increased, but not in a concentration-dependent manner. The spontaneous release of glutamine from mouse cerebellar slices was not altered by any concentration of methylmercury examined (10, 20, and 50 μM). The tissue content of glutamate, γ-aminobutyric acid, glutamine, and taurine decreased after exposure to methylmercury. Exposure of cerebellar slices to 20 μM methylmercury resulted in a significant enhancement in glutamate release during stimulation with 35 mM K+. This increase could be accounted for by the methylmercury-induced increase in spontaneous glutamate release. The increase in spontaneous release of glutamate and γ-aminobutyric acid was independent of the availability of extracellular calcium. These results suggest that methylmercury increases the release of neurotransmitter amino acids, particularly γ-aminobutyric acid and glutamate, by acting at intracellular sites to increase release from a neurotransmitter pool. The increase in the potassium-stimulated release of glutamate may reflect an increased sensitivity of the cerebellar granule cell to the effects of methylmercury. It is suggested that alterations in amino acid neurotransmitter function in the cerebellum may contribute to some of the neurological symptoms of methylmercury intoxication.

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Takeda, Kein, Yoshikazu Tanaka i Jun Kaneko. "The N-terminal amino-latch region of Hlg2 component of staphylococcal bi-component γ-haemolysin is dispensable for prestem release to form β-barrel pores". Journal of Biochemistry 168, nr 4 (24.04.2020): 349–54. http://dx.doi.org/10.1093/jb/mvaa052.

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Abstract The contribution of N-terminal regions of staphylococcal bi-component γ-haemolysin toxin components to haemolytic activity towards human erythrocyte cells was investigated in this study. A deletion construct of N-terminal amino acids 1–10 of Hlg2 (Hlg2 ΔN10), which is the S-component protein of γ-haemolysin, had little effect on its haemolytic activity, whereas N-terminal 1–11 amino acid deletion (Hlg2 ΔN11) significantly delayed haemolysis. Moreover, a deletion of N-terminal amino acids 1–17 of LukF, which is the F-component protein of γ-haemolysin, increased its haemolytic activity in combination with either the wild-type or Hlg2 ΔN10. Unlike the N-terminal amino-latch region of staphylococcal α-haemolysin, which is a single component β-barrel pore-forming toxin, the N-terminal regions present in γ-haemolysin components are dispensable for the haemolytic activity of the bi-component toxin. These results strengthen our recent proposal that staphylococcal bi-component γ-haemolysin toxin uses an N-terminal amino-latch independent molecular switch for prestem release during the formation of β-barrel pores.

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29

Appleton, TG, JR Hall i SF Ralph. "15N and 195Pt NMR-Study of the Effect of Chain-Length, n, on the Reactions of Amino-Acids, +NH3(CH2)NCO2 (N = 1, 2, 3), With Platinum(II) Ammine Complexes". Australian Journal of Chemistry 39, nr 9 (1986): 1347. http://dx.doi.org/10.1071/ch9861347.

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15N and 195Pt n.m.r. have been used to study the reactions in solution of cis -Pt(15NH3)2(H2O)22+ (1), cis -Pt(15NH3)2(OH)2 (2), cis -Pt(15NH3)2Cl2 (3), Pt(15NH3)3(H2O)2+ (4) and Pt(15NH3)3(OH)+ (5) with the amino acids +NH3(CH2)nCO2- (LH) [n = 1 ( glycine, glyH ); n = 2 (β- alanine , βalaH ), n = 3 (γ- aminobutyric acid, abaH )]. While glycine with (1) gives initially cis -Pt(NH3)2( glyH -O)(H2O)2+, with facile ring closure to Pt(NH3)2( gly - N,O)+, β- alanine and γ- aminobutyric acid with (1) give solutions containing a mixture of cis -Pt(NH3)2(LH-O)(H2O)2+, cis -Pt(NH3)2(LH.O)22+, and {Pt(NH3)2}2(μO,O-LH)(μ-OH)3+, which are quite stable kinetically under mildly acid conditions. Ring closure to Pt(NH3)2(L-N,O)+ becomes increasingly difficult as n increases. At 37°C and initial pH 7, (3) with glycine gives Pt(NH3)2( gly -N,O)+, but β- alanine and γ- aminobutyric acid give predominantly cis -Pt(NH3)2Cl(LH-O)+. Compound (4) with glycine gives initially Pt(NH3)3( glyH -O)2+, which then isomerizes to Pt(NH3)3( glyH -N)2+. In corresponding reactions with β- alanine and γ- aminobutyric acid, Pt(NH3)3(LH-O)2+ is stable indefinitely under mildly acid conditions. Differences in reactivity of the amino acids with (2) and (5) in alkaline solutions may be correlated with decreasing nucleophilicity of the amine group of NH2(CH2)nCO2- as n increases.

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30

Burky, Richard R., Donna L. Kirner, R. E. Taylor, P. E. Hare i John R. Southon. "14C Dating of Bone Using γ-Carboxyglutamic Acid and α-Carboxyglycine (Aminomalonate)". Radiocarbon 40, nr 1 (1997): 11–20. http://dx.doi.org/10.1017/s0033822200017823.

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Radiocarbon determinations have been obtained on γ-carboxyglutamic acid [Gla] and α-carboxyglycine (aminomalonate) [Am] as well as acid- and base-hydrolyzed total amino acids isolated from a series of fossil bones. As far as we are aware, Am has not been reported previously in fossil bone and neither Gla nor Am 14C values have been measured previously. Interest in Gla, an amino acid found in the non-collagen proteins osteocalcin and matrix Gla-protein (MGP), proceeds from the suggestion that it may be preferentially retained and more resistant to diagenetic contamination affecting 14C values in bones exhibiting low and trace amounts of collagen. Our data do not support these suggestions. The suite of bones examined showed a general tendency for total amino acid and Gla concentrations to decrease in concert. Even for bones retaining significant amounts of collagen, Gla (and Am extracts) can yield 14C values discordant with their expected age and with 14C values obtained on total amino-acid fractions isolated from the same bone sample.

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31

Palomo, Claudio, José I. Miranda i Anthony Linden. "New Approach to the Coupling of γ-Amino β-Hydroxy Acids and β,γ-Dihydroxy Acids with α-Amino Acid Esters". Journal of Organic Chemistry 61, nr 26 (styczeń 1996): 9196–201. http://dx.doi.org/10.1021/jo961219s.

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32

FLEMING, David E., Wilhelm VAN BRONSWIJK i Rosemary Lyons RYALL. "A comparative study of the adsorption of amino acids on to calcium minerals found in renal calculi". Clinical Science 101, nr 2 (20.06.2001): 159–68. http://dx.doi.org/10.1042/cs1010159.

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To assess the binding of individual amino acids to the principal calcium minerals found in human kidney stones, the adsorption of 20 amino acids on to calcium oxalate monohydrate, CaHPO4.2H2O, Ca3(PO4)2 and Ca5(PO4)3OH crystals was determined over the physiological urinary pH range (pH 5–8) in aqueous solutions. All amino acids adsorbed most strongly at pH 5, and this decreased in all cases as the pH was increased. The amino acids which adsorbed most strongly were aspartic acid, glutamic acid and γ-carboxyglutamic acid, with the last displaying the strongest affinity. All amino acids bound more avidly to calcium oxalate monohydrate than to any of the phosphate minerals. Adsorption on to CaHPO4.2H2O was generally higher than for Ca3(PO4)2 and Ca5(PO4)3OH, for which all amino acids, with the exception of γ-carboxyglutamic acid, had only a weak affinity. The binding affinity of these acids is thought to be due to their zwitterions being able to adopt conformations in which two carboxyl groups, and possibly the amino group, can interact with the mineral surface without further rotation. The strong binding affinity of di-and tri-carboxylic acids for calcium stone minerals indicates that proteins rich in these amino acids are more likely to play a functional role in stone pathogenesis than those possessing only a few such residues. These findings, as well as the preferential adsorption of the amino acids for calcium oxalate monohydrate rather than calcium phosphate minerals, have ramifications for research aimed at discovering the true role of proteins in stone formation and for potential application in the design of synthetic peptides for use in stone therapy.

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33

Grof, CPL, M. Johnston i PF Brownell. "Free Amino Acid Concentrations in Leaves of Sodium-Deficient C4 Plants". Functional Plant Biology 13, nr 3 (1986): 343. http://dx.doi.org/10.1071/pp9860343.

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Consistent changes in the free amino acid concentrations in response to sodium nutrition were observed in mature leaves of the C4 species Amaranthus tricolor and Chloris gayana. The amino acids alanine, γ-aminobutyric acid and glycine were present in greater and aspartate and arginine in lower concentrations in mature leaves of sodium-deficient than in normal plants of both species.

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34

HAELEWYN, Joost, Lieve MICHIELS, Peter VERHAERT, Marc F. HOYLAERTS, Raphaël WITTERS i Marc DE LEY. "Interaction of truncated human interferon γ variants with the interferon γ receptor: crucial importance of Arg-129". Biochemical Journal 324, nr 2 (1.06.1997): 591–95. http://dx.doi.org/10.1042/bj3240591.

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Recombinant human interferon γ (IFN-γ), produced in Escherichia coli, was selectively truncated at its C-terminus with chymotrypsin, clostripain or plasmin. The C-terminal amino acid residues of the three truncated IFN-γ variants were identified as Phe136, Arg129 and Lys128, indicating the removal of 7, 14 and 15 amino acid residues from the full-length molecule. The absence of seven C-terminal residues did not influence the binding of IFN-γ to its receptor. In contrast, the truncation of 14 residues resulted in a decrease in the Ka value to 1/24, as determined by surface plasmon resonance analysis. The removal of one additional amino acid residue from the C-terminal region of IFN-γ led to a marked loss of receptor-binding capacity and biological activity. These observations demonstrate that Arg129 is an essential part of a functionally important C-terminal IFN-γ sequence that is involved in receptor interaction.

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35

Golubev, Alexander S., Norbert Sewald i Klaus Burger. "Synthesis of γ-oxo α-amino acids from L-aspartic acid". Tetrahedron 52, nr 47 (listopad 1996): 14757–76. http://dx.doi.org/10.1016/0040-4020(96)00942-8.

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36

Zhang, Wenzhong, Wanxing Sha, Romana Pajkert, Haibo Mei, Yi Pan, Jianlin Han, Gerd-Volker Röschenthaler i Vadim A. Soloshonok. "β-Amino-γ,γ-difluoro-ω-phosphonoglutamic Acid Derivatives: An Unexplored, Multifaceted Structural Type of Tailor-Made α-Amino Acids". European Journal of Organic Chemistry 2017, nr 24 (26.06.2017): 3451–56. http://dx.doi.org/10.1002/ejoc.201700570.

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37

Meher, Hari Charan, Vijay T. Gajbhiye i Ghanendra Singh. "A GC-ECD Method for Estimation of Free and Bound Amino Acids, γ-Aminobutyric Acid, Salicylic Acid, and Acetyl Salicylic Acid from Solanum lycopersicum (L.)". Journal of AOAC INTERNATIONAL 94, nr 1 (1.01.2011): 232–42. http://dx.doi.org/10.1093/jaoac/94.1.232.

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Abstract A gas chromatograph with electron capture detection method for estimation of selected metabolites—amino acids (free and bound), γ-aminobutyric acid (GABA), salicylic acid (SA), and acetyl salicylic acid (ASA) from tomato—is reported. The method is based on nitrophenylation of the metabolites by 1-fluoro-2,4-dinitrobenzene under aqueous alkaline conditions to form dinitrophenyl derivatives. The derivatives were stable under the operating conditions of GC. Analysis of bound amino acids comprised perchloric acid precipitation of protein, alkylation (carboxymethylation) with iodoacetic acid, vapor-phase hydrolysis, and derivatization with 1-fluoro-2,4-dinitrobenzene in that order. The metabolites were resolved in 35 min, using a temperature-programmed run. The method is rapid, sensitive, and precise. It easily measured the typical amino acids (aspartate, asparagine, glutamate, glutamine, alanine, leucine, lysine, and phenylalanine) used for identification and quantification of a protein, resolved amino acids of the same mass (leucine and isoleucine), satisfactorily measured sulfur amino acids (methionine, cystine, and cysteine), and quantified GABA, SA, and ASA, as well. The developed method was validated for specificity, linearity, and precision. It has been applied and recommended for estimation of 25 metabolites from Solanum lycopersicum (L.).

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38

Corvo, M. C., i M. M. A. Pereira. "Synthesis of γ-amino acid analogues from natural α-amino acids by a radical pathway". Amino Acids 32, nr 2 (2.08.2006): 243–46. http://dx.doi.org/10.1007/s00726-006-0378-y.

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39

Gao, X., Y. Liu, P. X. Xu, Y. M. Cai i Y. F. Zhao. "α-Amino acid behaves differently from β- or γ-amino acids as treated by trimetaphosphate". Amino Acids 34, nr 1 (2.11.2007): 47–53. http://dx.doi.org/10.1007/s00726-007-0599-8.

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40

Pokrovsky, Vadim S., Olga E. Chepikova, Denis Zh Davydov, Andrey A. Zamyatnin Jr, Alexander N. Lukashev i Elena V. Lukasheva. "Amino Acid Degrading Enzymes and their Application in Cancer Therapy". Current Medicinal Chemistry 26, nr 3 (26.03.2019): 446–64. http://dx.doi.org/10.2174/0929867324666171006132729.

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Background:Amino acids are essential components in various biochemical pathways. The deprivation of certain amino acids is an antimetabolite strategy for the treatment of amino acid-dependent cancers which exploits the compromised metabolism of malignant cells. Several studies have focused on the development and preclinical and clinical evaluation of amino acid degrading enzymes, namely L-asparaginase, L-methionine γ-lyase, L-arginine deiminase, L-lysine α-oxidase. Further research into cancer cell metabolism may therefore define possible targets for controlling tumor growth.Objective:The purpose of this review was to summarize recent progress in the relationship between amino acids metabolism and cancer therapy, with a particular focus on Lasparagine, L-methionine, L-arginine and L-lysine degrading enzymes and their formulations, which have been successfully used in the treatment of several types of cancer.Methods:We carried out a structured search among literature regarding to amino acid degrading enzymes. The main aspects of search were in vitro and in vivo studies, clinical trials concerning application of these enzymes in oncology.Results:Most published research are on the subject of L-asparaginase properties and it’s use for cancer treatment. L-arginine deiminase has shown promising results in a phase II trial in advanced melanoma and hepatocellular carcinoma. Other enzymes, in particular Lmethionine γ-lyase and L-lysine α-oxidase, were effective in vitro and in vivo.Conclusion:The findings of this review revealed that therapy based on amino acid depletion may have the potential application for cancer treatment but further clinical investigations are required to provide the efficacy and safety of these agents.

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41

Chatterjee, Sunanda, Rituparna Sinha Roy i P. Balaram. "Expanding the polypeptide backbone: hydrogen-bonded conformations in hybrid polypeptides containing the higher homologues of α-amino acids". Journal of The Royal Society Interface 4, nr 15 (23.01.2007): 587–606. http://dx.doi.org/10.1098/rsif.2006.0203.

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Half a century has passed since the hydrogen-bonded secondary structures of polypeptides and proteins were first recognized. An extraordinary wealth of conformational information is now available on peptides and proteins, which are formed of α-amino acid residues. More recently, the discovery of well-folded structures in oligopeptides containing β-amino acids has focused a great deal of current interest on the conformational properties of peptides constructed from higher homologues (ω) of α-amino acids. This review examines the nature of intramolecularly hydrogen-bonded conformations of hybrid peptides formed by amino acid residues, with a varying number of backbone atoms. The β-turn, a ubiquitous structural feature formed by two residue (αα) segments in proteins and peptides, is stabilized by a 10-atom (C 10 ) intramolecular 4→1 hydrogen bond. Hybrid turns may be classified by comparison with their αα counterparts. The available crystallographic information on hydrogen-bonded hybrid turns is surveyed in this review. Several recent examples demonstrate that individual ω-amino acid residues and hybrid dipeptide segments may be incorporated into the regular structures of α-peptides. Examples of both peptide helices and hairpins are presented. The present review explores the relationships between folded conformations in hybrid sequences and their counterparts in all α-residue sequences. The use of stereochemically constrained ω-residues promises to expand the range of peptide design strategies to include ω-amino acids. This approach is exemplified by well-folded structures like the C 12 (αγ) and C 14 (γγ) helices formed in short peptides containing multiply substituted γ-residues. The achiral γ-residue gabapentin is a readily accessible building block in the design of peptides containing γ-amino acids. The construction of globular polypeptide structures using diverse hybrid sequences appears to be a realistic possibility.

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42

Sugiura, Masaharu, Chieko Mori, Keiichi Hirano i Shū Kobayashi. "Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine". Canadian Journal of Chemistry 83, nr 6-7 (1.06.2005): 937–42. http://dx.doi.org/10.1139/v05-096.

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Hydroxyglycine, the ammonia adduct of glyoxylic acid, was found to react with various allylboronates in the presence of triethylamine in methanol to give unprotected α-amino acids directly with high stereoselectivity. For instance, the reactions with (E)- and (Z)-crotylboronates afforded the corresponding anti- and syn-crotylated products (isoleucine and alloisoleucine after hydrogenation) with high diastereoselectivity, respectively. Interestingly, it was found that isomerization of the products (γ-adducts to α-adducts) occurred under the reaction conditions in some cases. Control experiments have suggested that the isomerization took place via 2-aza (or azonia) Cope rearrangement of imines derived from γ-adducts and glyoxylic acid.Key words: hydroxyglycine, glyoxylic acid, allylboronates, α-amino acids, allylglycines, isoleucine, alloisoleucine, stereoselective reactions, isomerization, 2-aza (azonia) Cope rearrangement.

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43

Przybylska, J., i B. Chwałek. "Free amino acids in different Lotus species". Acta Societatis Botanicorum Poloniae 40, nr 3 (2015): 439–50. http://dx.doi.org/10.5586/asbp.1971.032.

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Studies on free amino acid pools in various organs of different Lotus species showed mature seeds to be distinguished by a high concentration of canavanine and by the presence of γ-glutamyltyrosine and γ-glutamylphenylalanine. In seeds of <i>L. helleri</i> and <i>L. purshianus</i> homoarginine has been found which is interesting as the occurrence of this amino acid seemed to be restricted to the genus <i>Lathyrus</i>.

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44

Hosie, A. H. F., D. Allaway, C. S. Galloway, H. A. Dunsby i P. S. Poole. "Rhizobium leguminosarum Has a Second General Amino Acid Permease with Unusually Broad Substrate Specificity and High Similarity to Branched-Chain Amino Acid Transporters (Bra/LIV) of the ABC Family". Journal of Bacteriology 184, nr 15 (1.08.2002): 4071–80. http://dx.doi.org/10.1128/jb.184.15.4071-4080.2002.

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ABSTRACT Amino acid uptake by Rhizobium leguminosarum is dominated by two ABC transporters, the general amino acid permease (Aap) and the branched-chain amino acid permease (BraRl). Characterization of the solute specificity of BraRl shows it to be the second general amino acid permease of R. leguminosarum. Although BraRl has high sequence identity to members of the family of hydrophobic amino acid transporters (HAAT), it transports a broad range of solutes, including acidic and basic polar amino acids (l-glutamate, l-arginine, and l-histidine), in addition to neutral amino acids (l-alanine and l-leucine). While amino and carboxyl groups are required for transport, solutes do not have to be α-amino acids. Consistent with this, BraRl is the first ABC transporter to be shown to transport γ-aminobutyric acid (GABA). All previously identified bacterial GABA transporters are secondary carriers of the amino acid-polyamine-organocation (APC) superfamily. Also, transport by BraRl does not appear to be stereospecific as d amino acids cause significant inhibition of uptake of l-glutamate and l-leucine. Unlike all other solutes tested, l-alanine uptake is not dependent on solute binding protein BraCRl. Therefore, a second, unidentified solute binding protein may interact with the BraDEFGRl membrane complex during l-alanine uptake. Overall, the data indicate that BraRl is a general amino acid permease of the HAAT family. Furthermore, BraRl has the broadest solute specificity of any characterized bacterial amino acid transporter.

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Enders, Dieter, Qiang Liu, Xiang-Yu Chen, Sun Li, Fabrizio Vetica i Gerhard Raabe. "Two-Step Synthesis of α,β-Unsaturated γ-Amino Acid Esters via N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Enals and Nitroso Compounds". Synthesis 50, nr 01 (7.09.2017): 127–33. http://dx.doi.org/10.1055/s-0036-1590901.

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An efficient strategy for the synthesis of various of α,β-unsaturated γ-amino acid esters has been established employing N-heterocyclic carbene catalyzed [4+2] cycloadditions of β-methyl enals and aromatic nitroso compounds to afford 1,2-oxazin-6-ones in good yields. A subsequent acid-catalyzed esterification under ring opening yields the γ-amino enoates in good yields.

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46

Zhang, Rui, Jiamu Tan, Zhenzhen Luo, Haihong Dong, Ningshan Ma i Cangsong Liao. "Stereo-selective synthesis of non-canonical γ-hydroxy-α-amino acids by enzymatic carbon–carbon bond formation". Catalysis Science & Technology 11, nr 22 (2021): 7380–85. http://dx.doi.org/10.1039/d1cy00955a.

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Zhu, Ye, Sakunchai Khumsubdee, Amber Schaefer i Kevin Burgess. "Asymmetric Syntheses of α-Methyl γ-Amino Acid Derivatives". Journal of Organic Chemistry 76, nr 18 (16.09.2011): 7449–57. http://dx.doi.org/10.1021/jo201215c.

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Mitsuda, Teruhiko, Yoshika Hayakawa, Masanori Itoh, Kazunori Ohta i Toshiyuki Nakagawa. "ATF4 regulates γ-secretase activity during amino acid imbalance". Biochemical and Biophysical Research Communications 352, nr 3 (styczeń 2007): 722–27. http://dx.doi.org/10.1016/j.bbrc.2006.11.075.

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Kuroda, Yasuhisa, Hiroshi Ueda, Hiroshi Nozawa i Hisanobu Ogoshi. "Adamantyl amino acid as γ-turn inducer for peptide". Tetrahedron Letters 38, nr 45 (listopad 1997): 7901–4. http://dx.doi.org/10.1016/s0040-4039(97)10101-0.

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Antoni, Gunnar, i Bengt Långström. "Synthesis of γ-amino[4-11C]butyric acid (GABA)". Journal of Labelled Compounds and Radiopharmaceuticals 27, nr 5 (maj 1989): 571–76. http://dx.doi.org/10.1002/jlcr.2580270510.

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