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Thematische Bibliographien / Anomeric position

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Zeitschriftenartikel

Auswahl der wissenschaftlichen Literatur zum Thema „Anomeric position“

Autor: Grafiati

Veröffentlicht am 25. Mai 2024

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Zeitschriftenartikel zum Thema "Anomeric position"

1

Filho, João Rufino de Freitas, Jucleiton José Rufino de Freitas, Pedro Ramos de Souza Neto, et al. "Recent Advances Related to Anomeric and Exo-anomeric Effects in Carbohydrate Chemistry." International Research Journal of Pure and Applied Chemistry 24, no. 5 (2023): 95–110. http://dx.doi.org/10.9734/irjpac/2023/v24i5830.

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The anomeric effect in carbohydrate chemistry is known as the interaction between the OHd substituent at the anomeric position to favor an axial orientation rather than an equatorial one, despite the increased 1,3-diaxial interactions. In the anomeric effect, a sugar ring is stabilized by an electronegative substituent at the C1 carbon, also known as the anomeric carbon. The stabilization is thought to result from interactions between lone electron pairs on oxygen and a C1 antibonding orbital. On the other hand, the anomeric effect can be of two types: endo-anomeric and exo-anomeric. The effect is called endo-anomeric when the lone pair comes from the oxygen atom in the sugar ring and exo-anomeric when the lone pair comes from oxygen in a substituent on C1. Several factors influence the anomeric effect. In this way, this review aims to describe the recent advances in main theories, observations, and advances achieved in the last decades related to the anomeric effect. GRAPHICAL ABSTRACT

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2

Jabbari, Hadi. "Selective Anomeric Deacetylation of Per-Acetylated Carbohydrates Using (i-Pr)3Sn(OEt) and Synthesis of New Derivatives." Journal of Molecular Biology Research 10, no. 1 (2020): 166. http://dx.doi.org/10.5539/jmbr.v10n1p166.

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In this study natural carbohydrates such as glucose, galactose, xylose, fructose andlactose, are acetylated by acetic anhydride and sodium acetate catalyst. Anomeric configuration is deacetylated by (i-Pr)3Sn(OEt)as a catalyst, an easy synthetic regioselective deacetylation of full acetylated carbohydrates using (i--Pr)3Sn(OEt) is described. The acetylated carbohydrates reacted with HBr (solution in AcOH, 32 wt.%) for the bromination of anomeric position. The synthesis oxazaphosphorine, and bromo hexa alkyl Methylsulfonate derivatives from anomeric position of carbohydrates was reacted. FT IR, 1H, 13C NMR, 31PNMR spectroscopy techniques were employed to examine the synthesized compounds.

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3

Lee, Sang Jun, Dale E. A. Lewis, and Sankar Adhya. "Induction of the Galactose Enzymes in Escherichia coli Is Independent of the C-1-Hydroxyl Optical Configuration of the Inducer d-Galactose." Journal of Bacteriology 190, no. 24 (2008): 7932–38. http://dx.doi.org/10.1128/jb.01008-08.

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ABSTRACT The two optical forms of aldohexose galactose differing at the C-1 position, α-d-galactose and β-d-galactose, are widespread in nature. The two anomers also occur in di- and polysaccharides, as well as in glycoconjugates. The anomeric form of d-galactose, when present in complex carbohydrates, e.g., cell wall, glycoproteins, and glycolipids, is specific. Their interconversion occurs as monomers and is effected by the enzyme mutarotase (aldose-1-epimerase). Mutarotase and other d-galactose-metabolizing enzymes are coded by genes that constitute an operon in Escherichia coli. The operon is repressed by the repressor GalR and induced by d-galactose. Since, depending on the carbon source during growth, the cell can make only one of the two anomers of d-galactose, the cell must also convert one anomer to the other for use in specific biosynthetic pathways. Thus, it is imperative that induction of the gal operon, specifically the mutarotase, be achievable by either anomer of d-galactose. Here we report in vivo and in vitro experiments showing that both α-d-galactose and β-d-galactose are capable of inducing transcription of the gal operon with equal efficiency and kinetics. Whereas all substitutions at the C-1 position in the α configuration inactivate the induction capacity of the sugar, the effect of substitutions in the β configuration varies depending upon the nature of the substitution; methyl and phenyl derivatives induce weakly, but the glucosyl derivative does not.

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4

Ölgen, Süreyya, and Chung K. Chu. "Synthesis And Antiviral Activity Of 2'-Deoxy-2'-Fluoro-L-Arabinofuranosyl 1,2,3-Triazole Derivatives." Zeitschrift für Naturforschung B 56, no. 8 (2001): 804–11. http://dx.doi.org/10.1515/znb-2001-0814.

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The title compounds were prepared by building up the triazole ring at the anomeric position via the glycosyl azides 5 a,b. The anomeric configurations of these nucleosides were assigned by using 1H, 13C and NOESY NMR spectroscopy. The synthesized nucleosides were evaluated against HIV-1 and HBV

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5

Estevez, Juan C., Helen Ardron, Mark R. Wormald, David Brown, and George W. J. Fleet. "Spirocyclic peptides at the anomeric position of mannofuranose." Tetrahedron Letters 35, no. 47 (1994): 8889–90. http://dx.doi.org/10.1016/s0040-4039(00)78526-1.

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6

Tanzi, Lisa, Marina Simona Robescu, Sara Marzatico, et al. "Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks." Molecules 25, no. 23 (2020): 5764. http://dx.doi.org/10.3390/molecules25235764.

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Regioselective deprotection of acetylated mannose-based mono- and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells.

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7

Hain, Julia, Patrick Rollin, Werner Klaffke, and Thisbe K. Lindhorst. "Anomeric modification of carbohydrates using the Mitsunobu reaction." Beilstein Journal of Organic Chemistry 14 (June 29, 2018): 1619–36. http://dx.doi.org/10.3762/bjoc.14.138.

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The Mitsunobu reaction basically consists in the conversion of an alcohol into an ester under inversion of configuration, employing a carboxylic acid and a pair of two auxiliary reagents, mostly triphenylphosphine and a dialkyl azodicarboxylate. This reaction has been frequently used in carbohydrate chemistry for the modification of sugar hydroxy groups. Modification at the anomeric position, leading mainly to anomeric esters or glycosides, is of particular importance in the glycosciences. Therefore, this review focuses on the use of the Mitsunobu reaction for modifications of sugar hemiacetals. Strikingly, unprotected sugars can often be converted regioselectively at the anomeric center, whereas in other cases, the other hydroxy groups in reducing sugars have to be protected to achieve good results in the Mitsunobu procedure. We have reviewed on the one hand the literature on anomeric esterification, including glycosyl phosphates, and on the other hand glycoside synthesis, including S- and N-glycosides. The mechanistic details of the Mitsunobu reaction are discussed as well as this is important to explain and predict the stereoselectivity of anomeric modifications under Mitsunobu conditions. Though the Mitsunobu reaction is often not the first choice for the anomeric modification of carbohydrates, this review shows the high value of the reaction in many different circumstances.

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8

Wang, Ruibo, Kaimin Cai, Hua Wang, Chen Yin, and Jianjun Cheng. "A caged metabolic precursor for DT-diaphorase-responsive cell labeling." Chemical Communications 54, no. 38 (2018): 4878–81. http://dx.doi.org/10.1039/c8cc01715h.

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9

de Robichon, Morgane, Andrea Bordessa, Maciej Malinowski, Jacques Uziel, Nadège Lubin-Germain, and Angélique Ferry. "Access to C-aryl/alkenylglycosides by directed Pd-catalyzed C–H functionalisation of the anomeric position in glycal-type substrates." Chemical Communications 55, no. 78 (2019): 11806–8. http://dx.doi.org/10.1039/c9cc05993h.

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10

Sandoval, M., P. Hoyos, A. Cortés, T. Bavaro, M. Terreni та M. J. Hernáiz. "Development of regioselective deacylation of peracetylated β-d-monosaccharides using lipase from Pseudomonas stutzeri under sustainable conditions". RSC Adv. 4, № 98 (2014): 55495–502. http://dx.doi.org/10.1039/c4ra10401c.

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An efficient deacylation of peracetylated pyranosides has been developed in different biosolvents, catalyzed by Pseudomonas stutzeri lipase, which displayed regiospecific activity towards the anomeric position.

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