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Journal articles on the topic 'Guanidinium chloride'

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Published: 4 June 2021

Last updated: 11 February 2022

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1

Mazzini, Alberto, and Roberto Favilla. "The Effect of Guanidinium Chloride on the Self-Association of Bovine Liver Glutamate Dehydrogenase: A Gel Filtration Study." Zeitschrift für Naturforschung C 42, no. 3 (March 1, 1987): 217–20. http://dx.doi.org/10.1515/znc-1987-0308.

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The associative behaviour of bovine liver glutamate dehydrogenase has been studied by gel chromatography at neutral pH in 1 ᴍ guanidinium chloride and 1 ᴍ sodium chloride. In guanidinium chloride both the elution volume and the elution profile of the enzyme are independent of protein concentration, whereas in sodium chloride they are strongly dependent on it. In NaCl the enzyme behaves as expected according to the well established random association model, whereas in guanidinium chloride it appears to have completely lost the self-associative property. Furthermore, since the elution volume of the enzyme in guanidinium chloride corresponds to that of an hexamer, trimer formation reported to occur in these conditions is not confirmed by this technique.

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2

Kantlehner, Willi, Jochen Mezger, Ralf Kreß, Horst Hartmann, Thorsten Moschny, Ioannis Tiritiris, Boyan Iliev, et al. "Orthoamide, LXIX [1]. Beiträge zur Synthese N,N,N´,N´,N´´-peralkylierter Guanidine und N,N,N´,N´,N´´䞲,N´´-persubstituierter Guanidiniumsalze / Orthoamides, LXIX [1]. Contributions to the Synthesis of N, N, N´, N´, N´-peralkylated Guanidines and N, N, N´, N´, N´´, N´´-persubstituted Guanidinium Salts." Zeitschrift für Naturforschung B 65, no. 7 (July 1, 2010): 873–906. http://dx.doi.org/10.1515/znb-2010-0712.

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N, N, N´, N´-Tetraalkyl-chloroformamidinium chlorides 6 are prepared from N, N, N´, N´-tetraalkylureas 5 and phosgene in acetonitrile. The iminium salts 6 react with primary and secondary amines in the presence of triethylamine to give N, N, N´, N´, N´´-pentasubstituted and N, N, N´, N´, N´´, N´´- hexasubstituted guanidinium salts 7 and 8, respectively, Treatment of the guanidinium salts 7 with sodium hydroxide in excess affords the N, N, N´N´, N´´-pentasubstituted guanidines 9a - 9aa. Additionally, the N, N, N´, N´, N´´-pentasubstituted and N, N, N´, N´, N´´, N´´-hexasubstituted guanidinium salts 7l´, 7p´ and 8a - c can be obtained from the reaction mixtures by addition of stoichiometric amounts of sodium hydroxide. A modified method is described for the preparation of guanidinium salts possessing dialkylamino substituents consisting of two long-chain alkyl groups (>C14). Some guanidines 9 were alkylated with allyl chloride and bromide, ethyl bromide, butyl bromide, benzyl bromide and chloride, dimethyl sulfate, diethyl sulfate, and methyl methansulfonate to give the corresponding guanidinium salts 11 - 15. By alkylation of the N, N, N´, N´, N´´-pentasubstituted guanidine 9v with triethyloxonium tetrafluoroborate the guandinium tetrafluoroborate 16a is accessible. N-Functionalized guanidinium salts 17 - 18a - c result from the reaction of N, N, N´, N´, N´´-pentasubstituted guanidines with ethyl bromoacetate and bromoacetonitrile, respectively, and subsequent anion exchange with sodium tetraphenylborate. N, N, N´, N´-Tetramethylguanidine (21) adds to ethyl acrylate to give the labile guanidine 22, which forms the guanidinium salt 23a on treatment with methyl iodide. Zwitterionic guanidinium salts 25 result, when N, N, N´, N´, N´´-pentasubstituted guanidines are treated with sultones 24.

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3

Puri, N. K., E. Crivelli, M. Cardamone, R. Fiddes, J. Bertolini, B. Ninham, and M. R. Brandon. "Solubilization of growth hormone and other recombinant proteins from Escherichia coli inclusion bodies by using a cationic surfactant." Biochemical Journal 285, no. 3 (August 1, 1992): 871–79. http://dx.doi.org/10.1042/bj2850871.

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Recombinant pig growth hormone (rPGH) was solubilized from inclusion bodies by using the cationic surfactant cetyltrimethylammonium chloride (CTAC). The solubilizing action of CTAC appeared to be dependent on the presence of a positively charged head group, as a non-charged variant was inactive. Relatively low concentrations of CTAC were required for rapid solubilization, and protein-bound CTAC was easily removed by ion-exchange chromatography. Compared with solubilization and recovery of rPGH from inclusion bodies with 7.5 M-urea and 6 M-guanidinium chloride, the relative efficiency of solubilization was lower with CTAC. However, superior refolding efficiency resulted in final yields of purified rPGH being in the order of CTAC greater than urea greater than or equal to guanidinium chloride. Detailed comparison of the different rPGH preparations as well as pituitary-derived growth hormone by h.p.l.c., native PAGE, c.d. spectral analysis and radioreceptor-binding assay showed that the CTAC-derived rPGH was essentially indistinguishable from the urea and guanidinium chloride preparations. The CTAC-derived rPGH was of greater biopotency than pituitary-derived growth hormone. The advantages of CTAC over urea and guanidinium chloride for increasing recovery of monomeric rPGH by minimizing aggregation during refolding in vitro were also found with recombinant sheep interleukin-I beta and a sheep insulin-like growth factor II fusion protein. In addition, the bioactivity of the CTAC-derived recombinant interleukin-1 beta was approximately ten-fold greater than that of an equivalent amount obtained from urea and guanidinium chloride preparations. It is concluded that CTAC represents, in general, an excellent additional approach or a superior alternative to urea and in particular guanidinium chloride for solubilization and recovery of bioactive recombinant proteins from inclusion bodies.

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4

Goward, C. R., L. I. Irons, J. P. Murphy, and T. Atkinson. "The secondary structure of protein G′, a robust molecule." Biochemical Journal 274, no. 2 (March 1, 1991): 503–7. http://dx.doi.org/10.1042/bj2740503.

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The secondary structure of recombinant streptococcal Protein G' was predicted and compared with spectropolarimetric data. The predicted secondary structure consisted of 37 +/- 4% alpha-helix and 30 +/- 5% beta-sheet, whereas the values obtained from c.d. data were 29 +/- 2% alpha-helix and 41 +/- 3% beta-sheet. An alpha-helix-beta-sheet/turn-alpha-helix motif is conjectured to comprise the Fc-binding unit. The c.d. spectra in the near u.v. and far u.v. show that the Protein G' molecule is stable to heating at 100 degrees C and to extremes of pH (pH 1.5 to 11.0). The protein retained biological activity at these extremes. The molecule uncoils above pH 11.5 in a time-dependent fashion. Unfolding of the molecule in guanidinium chloride was monitored by c.d. and fluorescence emission; 3 M-guanidinium chloride was required to unfold the protein by 50%. The protein was completely unfolded in 5.5 M-guanidinium chloride and fully refolded with restoration of activity after removal of guanidinium chloride.

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5

Kantlehner, Willi, Ralf Kreß, Jochen Mezger, and Georg Ziegler. "Orthoamide und Iminiumsalze, LXXXVIII. Synthese N,N,N′,N′,N″,N″-persubstituierter Guanidiniumsalze aus N,N′-persubstituierten Harnstoff/Säurechlorid-Addukten**." Zeitschrift für Naturforschung B 70, no. 1 (January 1, 2015): 9–27. http://dx.doi.org/10.1515/znb-2014-0102.

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AbstractN,N,N′,N′,N″,N″-Hexamethylguanidinium chloride9cwas prepared by treating the reaction mixture formed fromN,N,N′,N′-tetramethylurea (1a) and phthaloyl chloride (16) with dimethyltrimethylsilylamine15.N,N,N′,N′-Tetramethyl-chloroformamidinium chloride (2a) is an intermediate in this synthesis. The chloroformamidinium chloride2acan also be prepared by treating the urea1awith thionyl chloride or phosphorus pentachloride, respectively. The guanidinium salt9ccan be obtained from the crude2athus prepared and the silylamine15. From urea/phosphoryl chloride adducts and primary aromatic amines have been prepared guanidines38, which are converted toN,N′-diaryl-N,N′,N″,N″-tetramethyl-guanidinium iodides39on treatment with methyl iodide. TheN,N′,N″-trimethyl-N,N′,N″-triphenylguanidinium salt44awas prepared from the chloroformamidinium salt43andN-methylaniline. The guanidinium salt9cis the reaction product when the urea1a/POCl3adduct is treated with the silylamine15.

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6

Ring, Joshua R., Sean Parkin, and Peter A. Crooks. "(4-Methoxy-3-nitrobenzylideneamino)guanidinium chloride." Acta Crystallographica Section C Crystal Structure Communications 63, no. 7 (June 14, 2007): o392—o394. http://dx.doi.org/10.1107/s0108270107023475.

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7

Wang, Bei, Pei-Zhi Zhang, Xin Chen, Ai-Quan Jia, and Qian-Feng Zhang. "Syntheses and crystal structures of guanidine hydrochlorides with two Schiff base functions as efficient colorimetric and selective sensors for fluoride." Zeitschrift für Naturforschung B 73, no. 8 (August 28, 2018): 601–9. http://dx.doi.org/10.1515/znb-2018-0102.

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AbstractA series of guanidinium chloride derivatives have been synthesized by condensation of 1,3-diaminoguanidine monohydrochloride with heteroaromatic formaldehydes in good yields. All compounds were characterized by nuclear magnetic resonances and infrared spectroscopies, and the molecular structures of four compounds were determined by single crystal X-ray diffraction. The optical properties of these guanidinium chloride derivatives with fluoride anions were investigated, showing selective color changes from colorless to yellow or orange, red-shifted in the ultraviolet/visible absorption spectra.

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8

Mayr, Lorenz M., and Franz X. Schmid. "Stabilization of a protein by guanidinium chloride." Biochemistry 32, no. 31 (August 1993): 7994–98. http://dx.doi.org/10.1021/bi00082a021.

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9

Serra, M. A., and R. B. Honzatko. "Structure of 1-(p-nitrobenzylidineamino)guanidinium chloride." Acta Crystallographica Section C Crystal Structure Communications 42, no. 12 (December 15, 1986): 1755–57. http://dx.doi.org/10.1107/s0108270186090686.

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10

Mohamed, Shaaban K., Peter N. Horton, Mahmoud A. A. El-Remaily, and Seik Weng Ng. "2-(1,3-Benzothiazol-2-yl)guanidinium chloride." Acta Crystallographica Section E Structure Reports Online 67, no. 11 (October 29, 2011): o3132. http://dx.doi.org/10.1107/s1600536811044643.

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11

Mohamed, Shaaban K., Peter N. Horton, Mahmoud A. A. El-Remaily, and Seik Weng Ng. "2-(1,3-Benzoxazol-2-yl)guanidinium chloride." Acta Crystallographica Section E Structure Reports Online 67, no. 11 (October 29, 2011): o3133. http://dx.doi.org/10.1107/s1600536811044655.

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12

Mason, Philip E., George W. Neilson, John E. Enderby, Marie-Louise Saboungi, Christopher E. Dempsey, Alexander D. MacKerell, and John W. Brady. "The Structure of Aqueous Guanidinium Chloride Solutions." Journal of the American Chemical Society 126, no. 37 (August 27, 2004): 11462–70. http://dx.doi.org/10.1021/ja040034x.

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13

Sonar, Vijayakumar N., Sundar Neelakantan, Maxime Siegler, and Peter A. Crooks. "(E)-1-[(2-Methoxyphenyl)methyleneamino]guanidinium chloride." Acta Crystallographica Section E Structure Reports Online 63, no. 2 (January 10, 2007): o535—o536. http://dx.doi.org/10.1107/s1600536806055383.

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14

Sonar, Vijayakumar N., Joshua R. Ring, Maxime Siegler, and Peter A. Crooks. "(E)-1-[(2-Chlorophenyl)methyleneamino]guanidinium chloride." Acta Crystallographica Section E Structure Reports Online 63, no. 2 (January 31, 2007): o974—o975. http://dx.doi.org/10.1107/s1600536807002887.

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15

CALMETTES, P., D. DURAND, J. C. SMITH, M. DESMADRIL, P. MINARD, and R. DOUILLARD. "Structure of proteins unfolded by guanidinium chloride." Le Journal de Physique IV 03, no. C8 (December 1993): C8–253—C8–256. http://dx.doi.org/10.1051/jp4:1993849.

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16

Wei, Bin. "Guanidinium chloride–18-crown-6 (2/1)." Acta Crystallographica Section E Structure Reports Online 68, no. 5 (April 21, 2012): o1490. http://dx.doi.org/10.1107/s1600536812016959.

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17

Makhatadze, George I., and Peter L. Privalov. "Protein interactions with urea and guanidinium chloride." Journal of Molecular Biology 226, no. 2 (July 1992): 491–505. http://dx.doi.org/10.1016/0022-2836(92)90963-k.

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18

Bogdanov, Milen G., Desislava Petkova, Stanimira Hristeva, Ivan Svinyarov, and Willi Kantlehner. "New Guanidinium-based Room-temperature Ionic Liquids. Substituent and Anion Effect on Density and Solubility in Water." Zeitschrift für Naturforschung B 65, no. 1 (January 1, 2010): 37–48. http://dx.doi.org/10.1515/znb-2010-0108.

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In order to examine the influence of the alkyl chain length on some physical properties of guanidinium salts, the synthesis of a homologous series of new N″-n-alkylsubstituted N,N-diethyl-N′ ,N′- di-n-propyl-N″-n-hexyl guanidinium ionic liquids (gILs), containing chloride (Cl), tetrafluoroborate (BF4), acesulfamate (Ace), saccharinate (Sac), and tosylate (Tos) as anions, is reported. Cn-gILAce, Cn-gILSac, and Cn-gILBF4 were obtained by ion exchange reaction of the corresponding hexasubstituted guanidinium chlorides (Cn-gCl, n = 3, 4, 6, 8, 10), which were synthesized by a quaternization reaction of the pentaalkyl-substituted guanidine 3 and the corresponding alkylchloride in DMF. The tosylates gILs Cn-gTos (n = 1, 2, 4, 6, 8, 10) were synthesized by alkylation of 3 with the corresponding alkyltosylates. Some physical properties, such as solubility in water and organic solvents, refractive index and density, are considered as a function of the length of the n-alkyl substituent R and the nature of the anion

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19

Szabo, Jan, and Gerhard Maas. "Derivatives of the triaminoguanidinium ion, 6. Aminal-forming reactions with aldehydes and ketones." Zeitschrift für Naturforschung B 75, no. 3 (February 25, 2020): 317–26. http://dx.doi.org/10.1515/znb-2019-0216.

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AbstractCyclic aminals (N,N-acetals) could be prepared by the reaction of N,N′,N″-triaminoguanidinium sulfate, N,N′,N″-tris(benzylamino)guanidinium chloride or N,N′,N″-tris(benzylamino)guanidine with formaldehyde or acetone. In all cases, 1,2,4,5-tetrazinane derivatives were obtained, which were structurally confirmed by X-ray crystal structure determinations. In two cases, 1:1 cocrystals of two different tetrazinane products were isolated. On the other hand, the reaction of N,N′,N″-tris(benzylamino)guanidinium chloride with benzaldehyde yielded a 3-(2-benzylidenehydrazin-1-yl)-1H-1,2,4-triazole.

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20

Kantlehner, Willi, Heinz Malik, and Ralf Kreß. "Orthoamide und Iminiumsalze, C. Vinyloge Guanidiniumsalz-basierte ionische Flüssigkeiten sowie phenyloge Guanidiniumsalze und Orthoamide." Zeitschrift für Naturforschung B 75, no. 6-7 (August 27, 2020): 697–708. http://dx.doi.org/10.1515/znb-2019-0231.

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AbstractCyclopropylacetylene and N,N,N′,N′,N′′,N′′-hexamethylguanidinium chloride (1a) react to give the orthoamide derivative 8c, in the presence of sodium hydride. 8c is transformed by elemental iodine to the vinylogous guanidinium salt 6f. Anion metathesis with the salts 5a, 5e, 6g delivers vinylogous guanidinium salts 5e–5i, 12a with counter ions derived from carbon acids (tricyanomethane, 1,1,3,3-tetracyano-propene). Phenylogous amidinium salts 15 guanidinium salts 19, 21 and the phenylogous orthoamide derivatives of formic acid 18 and carbonic acid 33 have been prepared.

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21

Ratcliffe, Christopher I. "Nuclear magnetic resonance studies of molecular motion in guanidinium chloride, bromide, and iodide." Canadian Journal of Chemistry 63, no. 6 (June 1, 1985): 1239–44. http://dx.doi.org/10.1139/v85-211.

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Guanidinium [Formula: see text] chloride, bromide, and iodide salts have been studied by 1H and 2H nmr as a function of temperature. The 2H powder lineshapes show conclusively that reorientation of the guanidinium ion occurs about the principal three-fold axis in the chloride, bromide, and high temperature phase of the iodide. Activation energies for this process have been obtained from 1H spin-lattice relaxation results. The question of whether or not there are concurrent two-fold flips of the —NH2 units is discussed, but must presently remain unresolved. It was found that the high temperature phase of the iodide can be supercooled.

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22

Venn, G., and R. M. Mason. "Changes in mouse intervertebral-disc proteoglycan synthesis with age. Hereditary kyphoscoliosis is associated with elevated synthesis." Biochemical Journal 234, no. 2 (March 1, 1986): 475–79. http://dx.doi.org/10.1042/bj2340475.

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Mice with hereditary kyphoscoliosis (ky/ky) develop intervertebral-disc degeneration at the cervico-thoracic junction. Disc proteoglycans were investigated to determine whether changes in synthesis or structure were associated with this. Elevated 35S-proteoglycan synthesis was found in one or more cervico-thoracic discs in 80-day-old ky/ky mice. The hydrodynamic size and aggregation properties of ky/ky-mouse disc 35S-proteoglycans extracted with 4 M-guanidinium chloride were normal. Increased proportions of small 35S-proteoglycans were extracted with 0.5 M-guanidinium chloride from discs of normal and ky/ky mice with increasing age.

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23

Graziano, Giuseppe. "Contrasting the denaturing effect of guanidinium chloride with the stabilizing effect of guanidinium sulfate." Physical Chemistry Chemical Physics 13, no. 25 (2011): 12008. http://dx.doi.org/10.1039/c1cp20843h.

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24

Gros, P., P. Le Perchec, P. Gauthier, and J. P. Senet. "Selective Esterification Reaction Involving Hexaalkyl Guanidinium Chloride Catalyst." Synthetic Communications 23, no. 13 (July 1993): 1835–42. http://dx.doi.org/10.1080/00397919308011284.

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25

Godawat, Rahul, Sumanth N. Jamadagni, and Shekhar Garde. "Unfolding of Hydrophobic Polymers in Guanidinium Chloride Solutions." Journal of Physical Chemistry B 114, no. 6 (February 18, 2010): 2246–54. http://dx.doi.org/10.1021/jp906976q.

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26

Grimsley, Gerald R., Beatrice M. P. Huyghues-Despointes, C. Nick Pace, and J. Martin Scholtz. "Determining a Urea or Guanidinium Chloride Unfolding Curve." Cold Spring Harbor Protocols 2006, no. 1 (January 1, 2006): pdb.prot4242. http://dx.doi.org/10.1101/pdb.prot4242.

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27

Szabo, Jan, Kerstin Karger, Nicolas Bucher, and Gerhard Maas. "Derivatives of the triaminoguanidinium ion, 3. Multiple N-functionalization of the triaminoguanidinium ion with isocyanates and isothiocyanates." Beilstein Journal of Organic Chemistry 10 (September 24, 2014): 2255–62. http://dx.doi.org/10.3762/bjoc.10.234.

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1,2,3-Triaminoguanidinium chloride was combined with benzaldehyde and hydratropic aldehyde to furnish the corresponding tris(imines), which were converted into 1,2,3-tris(benzylamino)guanidinium salts by catalytic hydrogenation in the former, and by borane reduction in the latter case. The resulting alkyl-substituted triaminoguanidinium salts underwent a threefold carbamoylation with aryl isocyanates to furnish 1,2,3-tris(ureido)guanidinium salts, while p-toluenesulfonyl isocyanate led only to a mono-ureido guanidinium salt. With aryl isothiocyanates, 3-hydrazino-1H-1,2,4-triazole-5(4H)-thione derivatives were obtained. Compounds 7a and 8 show interesting solid-state structures with intra- and intermolecular hydrogen bonds.

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28

Flemström, Andreas, Simina Vintila, and Sven Lidin. "Inheritance of the guanidinium chloride structure in two molybdenum (II) chloride salts." Comptes Rendus Chimie 8, no. 11-12 (November 2005): 1750–59. http://dx.doi.org/10.1016/j.crci.2005.06.002.

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29

Mandal, Manoj, and Chaitali Mukhopadhyay. "Microsecond molecular dynamics simulation of guanidinium chloride induced unfolding of ubiquitin." Phys. Chem. Chem. Phys. 16, no. 39 (2014): 21706–16. http://dx.doi.org/10.1039/c4cp01657b.

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30

Wong, H. J., J. E. Aubin, S. Wasi, and J. Sodek. "Cell adhesion to low-Mr proteins extractable from mineralized and soft connective tissues." Biochemical Journal 232, no. 1 (November 15, 1985): 119–23. http://dx.doi.org/10.1042/bj2320119.

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Guanidinium chloride (4 M) containing proteinase inhibitors was used to extract proteins from porcine calvariae and long bones. The extracted proteins were separated on polyacrylamide slab gels and transferred electrophoretically to nitrocellulose strips. Proteins with cell-adhesion properties were identified by incubating the strips with cells and staining with Amido Black. In addition to binding to fibronectin, both bone cells and fibroblast-like cells adhered to proteins of Mr approximately 30 000 and approximately 14 000-17 000. 4 M-Guanidinium chloride extracts of porcine skin and gingiva yielded cell-binding proteins with similar Mr values. These data suggest that these low-Mr proteins may have a general cell-adhesion function in both soft and mineralized connective tissues.

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31

White, M. F., L. A. Fothergill-Gilmore, S. M. Kelly, and N. C. Price. "Dissociation of the tetrameric phosphoglycerate mutase from yeast by a mutation in the subunit contact region." Biochemical Journal 295, no. 3 (November 1, 1993): 743–48. http://dx.doi.org/10.1042/bj2950743.

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Phosphoglycerate mutases from different sources exhibit a variety of quaternary structures (tetramer, dimer and monomer). To perturb the tetrameric structure of yeast phosphoglycerate mutase we have prepared a mutant enzyme in which Lys-168 in the subunit-contact region has been replaced by proline. The K168P mutant enzyme undergoes dissociation to dimers at low concentrations; thus on lowering the concentration from 200 micrograms/ml to 5 micrograms/ml the proportion of tetramer falls from 85% to 53%. The tetrameric structure of the wild-type enzyme remains intact over this range of concentrations. The mutant enzyme has similar kinetic properties to the wild-type enzyme, with kcat. being reduced by 26%. Far-u.v. c.d. studies show that there has been a small loss of helical structure in the mutant. Compared with wild-type enzyme, the K168P mutant enzyme is slightly less stable towards proteolysis by trypsin, but significantly less stable towards denaturation by guanidinium chloride, with the midpoint concentration of guanidinium chloride some 50% lower. After denaturation, the mutant enzyme could regain activity and quaternary structure when the guanidinium chloride concentration was lowered to 0.05 M. The properties of the mutant enzyme are discussed in terms of other dimeric phosphoglycerate and bisphosphoglycerate mutases which contain proline at position 168.

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32

Hutchinson, J. P., T. S. el-Thaher, and A. D. Miller. "Refolding and recognition of mitochondrial malate dehydrogenase by Escherichia coli chaperonins cpn 60 (groEL) and cpn10 (groES)." Biochemical Journal 302, no. 2 (September 1, 1994): 405–10. http://dx.doi.org/10.1042/bj3020405.

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In vitro refolding of pig mitochondrial malate dehydrogenase is investigated in the presence of Escherichia coli chaperonins cpn60 (groEL) and cpn10 (groES). When the enzyme is initially denatured with 3 M guanidinium chloride, chaperonin-assisted refolding is 100% efficient. C.d. spectroscopy reveals that malate dehydrogenase is almost unfolded in 3 M guanidinium chloride, suggesting that a state with little or no residual secondary structure is the optimal ‘substrate’ for chaperonin-assisted refolding. Malate dehydrogenase denatured to more highly structured states proves to refold less efficiently with chaperonin assistance. The enzyme is shown not to aggregate under the refolding conditions, so that losses in refolding efficiency result from irreversible misfolding. Evidence is advanced to suggest that the chaperonins are unable to rescue irreversibly misfolded malate dehydrogenase. A novel use is made of 100 K Centricon concentrators to study the binding of [14C]acetyl-labelled malate dehydrogenase to groEL by an ultrafiltration binding assay. Analysis of the data by Scatchard plot shows that acetyl-malate dehydrogenase, which has previously been extensively unfolded with guanidinium chloride, binds to groEL at a specific binding site(s). At saturation, one acetyl-malate dehydrogenase homodimer (two polypeptides) is shown to bind to each groEL homooligomer with a binding constant of approx. 10 nM.

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33

Tiritiris, Ioannis, and Willi Kantlehner. "Orthoamide und Iminiumsalze, LXXIX [1]. N-[w-(Dimethylamino)alkyl]-N´,N´,N´´,N´´-tetramethylguanidine und davon abgeleitete Guanidiniumsalze: Synthese und Kristallstrukturen/ Orthoamides and Iminium Salts, LXXIX [1]. N-[w-(Dimethylamino)alkyl]-N´,N´,N´´,N´´- tetramethylguanidines and Salts Derived therefrom: Synthesis and Crystal Structures." Zeitschrift für Naturforschung B 67, no. 7 (July 1, 2012): 685–98. http://dx.doi.org/10.5560/znb.2012-0061.

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N-(ω-Dimethylammonioalkyl)-N´,N´,N´´,N´´-tetramethylguanidinium-dichlorides 5a, b are obtained from the chloroformamidinium salt 2 and diamines 3a, b. Their crystal structures reveal that the guanidinium ions are associated with the chloride ions via N-H· · ·Cl hydrogen bonds. By deprotonation of 5a, b with one equivalent of sodium hydroxide, the guanidinium chlorides 4a, b are accessible, and a further deprotonation leads to the aminoguanidines 6a, b, which hydrolyze in the presence of excessive aqueous sodium hydroxide to give the aminoalkylureas 7a, b. The salts 9a, b and 10a, b were synthesized from 4a, b and 5a, b, respectively, by anion metathesis by means of sodium tetraphenylborate. 7a reacts with dimethyl sulfate to give the waxy ammonium salt 11a, which was converted to the crystalline tetraphenylborate salt 12a. The crystal structures of all the tetraphenylborates were determined by single-crystal X-ray diffraction analysis.

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34

Olyaei, Abolfazl, Amir Mohamadi, and Nilufar Rahmani. "Green synthesis of new lawsone enaminones and their Z/E(CC)-isomerization induced by organic solvent." RSC Advances 11, no. 21 (2021): 12990–94. http://dx.doi.org/10.1039/d1ra01858b.

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The synthesis of a new class of lawsone enaminone derivatives by using lawsone, triethyl orthoformate and aromatic amines in the presence of guanidinium chloride under solvent-free conditions has been developed.

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35

Garcia-Mira, Maria M., and Jose M. Sanchez-Ruiz. "pH Corrections and Protein Ionization in Water/Guanidinium Chloride." Biophysical Journal 81, no. 6 (December 2001): 3489–502. http://dx.doi.org/10.1016/s0006-3495(01)75980-2.

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36

Sudha, L., K. Subramanian, J. Senthil Selvan, Th Steiner, G. Koellner, K. Ramdas, and N. Srinivasan. "3,3-(Oxydiethyl)-1,2-di(o-methylphenyl)guanidinium Chloride Monohydrate." Acta Crystallographica Section C Crystal Structure Communications 52, no. 12 (December 15, 1996): 3238–40. http://dx.doi.org/10.1107/s0108270196011274.

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37

Weakley, T. J. R., M. W. Scherz, and J. F. W. Keana. "N-Adamant-1-yl-N'-(2-iodophenyl)guanidinium chloride." Acta Crystallographica Section C Crystal Structure Communications 46, no. 11 (November 15, 1990): 2234–36. http://dx.doi.org/10.1107/s0108270190002918.

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38

Ahmad, F., S. Yadav, and S. Taneja. "Determining stability of proteins from guanidinium chloride transition curves." Biochemical Journal 287, no. 2 (October 15, 1992): 481–85. http://dx.doi.org/10.1042/bj2870481.

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The guanidinium chloride (GdmCl) denaturation of RNAase A, lysozyme and metmyoglobin was investigated at several pH values by using absorbance measurements at 287, 300 and 409 nm respectively. From these measurements the free-energy change on denaturation, delta Gapp., was calculated, assuming a two-state mechanism, and values of delta Gapp. at zero concentration of the denaturant were measured. For each protein all delta Gapp. values were adjusted to pH 7.00 by using the appropriate relationship between delta Gapp. and pH. Dependence of the adjusted delta Gapp. value on GdmCl concentration increases for metmyoglobin and decreases for the other two proteins as the denaturant concentration decreases. It has been shown that these are expected results if the presence of the acid-denatured state during the GdmCl denaturation of proteins is considered.

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39

Matyushin, Yu N., T. S. Kon'kova, K. V. Titova, V. Ya Rosolovskii, and Yu A. Lebedev. "Enthalpy of formation of guanidinium nitrate, perchlorate, and chloride." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 4 (April 1985): 713–16. http://dx.doi.org/10.1007/bf00948042.

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40

Khan, M. Y., M. S. Medow, and S. A. Newman. "Unfolding transitions of fibronectin and its domains. Stabilization and structural alteration of the N-terminal domain by heparin." Biochemical Journal 270, no. 1 (August 15, 1990): 33–38. http://dx.doi.org/10.1042/bj2700033.

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Changes in the conformational state of human plasma fibronectin and several of its fragments were studied by fluorescence emission, intrinsic fluorescence polarization and c.d. spectroscopy under conditions of guanidinium chloride-and temperature-induced unfolding. Fragments were chosen to represent all three types of internal structural homology in the protein. Low concentration (less than 2 M) of guanidinium chloride induced a gradual transition in the intact protein that was not characteristic of any of the isolated domains, suggesting the presence of interdomain interactions within the protein. Intermediate concentrations of guanidinium chloride (2-3 M) and moderately elevated temperatures (55-60 degrees C) induced a highly co-operative structural transition in intact fibronectin that was attributable to the central 110 kDa cell-binding domain. High temperatures (greater than 60 degrees C) produced a gradual unfolding in the intact protein attributable to the 29 kDa N-terminal heparin-binding and 40 kDa collagen-binding domains. Binding of heparin to intact fibronectin and to its N-terminal fragment stabilized the proteins against thermal unfolding. This was reflected in increased delta H for the unfolding transitions of the heparin-bound N-terminal fragment, as well as decreased accessibility to solvent perturbants of internal chromophores in this fragment when bound to heparin. These results help to account for the biological efficacy of the interaction between the fibronectin N-terminal domain and heparin, despite its relatively low affinity.

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41

Takeuchi, Y., T. Matsumoto, E. Ogata, and Y. Shishiba. "Isolation and characterization of proteoglycans synthesized by mouse osteoblastic cells in culture during the mineralization process." Biochemical Journal 266, no. 1 (February 15, 1990): 15–24. http://dx.doi.org/10.1042/bj2660015.

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Proteoglycans in mineralized (0.5 M-EDTA/4 M-guanidinium chloride-extractable) and non-mineralized (4 M-guanidinium chloride-extractable) matrices synthesized by a mouse osteoblastic-cell line MC3T3-E1 were characterized at different phases of mineralization in vitro. Cell cultures were labelled with [35S]sulphate and either [3H]glucosamine or 3H-labelled amino acids. At the mineralization phase a large majority of proteoglycans were extracted with 4 M-guanidinium chloride (G extract), and at least five species of labelled proteoglycans were identified; dermatan sulphate proteoglycans (DSPG), apparent Mr approx. 120,000 and 70,000), heparan sulphate proteoglycans (HSPG, apparent Mr approx. 200,000 and 120,000) and DS chains with very little core protein. DSPGs weakly bound to an octyl-Sepharose CL-4B column and HSPGs bound more tightly, whereas DS chains did not bind to the column. Amounts of labelled proteoglycans extracted with 0.5 M-EDTA/4 M-guanidinium chloride (EDTA extract) were much less than those in G extract. Although the predominant species in the EDTA extract were comparable with the DS or DSPGs in the G extract, none of them bound to octyl-Sepharose CL-4B, indicating their lack of hydrophobicity. At the nonmineralizing phase a large chondroitin sulphate proteoglycan (Mr greater than 600,000) was found in the matrix in addition to the five proteoglycan species similar to those at the mineralization phase. Although DS chains at the early phase were similar in size to those at the mineralization phase, the ratio of 2-acetamido-2-deoxy-3-O-(beta-D-gluco-4-enepyranosyluronic acid)-4-O-sulpho-D-galactose to 2-acetamido-2-deoxy-3-O-(beta-D-gluculo-4-enepyranosyluronic acid)-6-O-sulpho-D-galactose was less than that at the mineralization phase. These results agree with those of previous studies performed in vivo and suggest that alteration in the synthesis of proteoglycans is involved in the mineralization process. They also suggest that at the osteoblastic mineralization front proteoglycans undergo partial degradation and lose their hydrophobicity.

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42

Tiritiris, Ioannis, and Willi Kantlehner. "N,N,N′,N′-Tetramethyl-N′′,N′′-dipropylguanidinium chloride–(2Z)-2,3-diaminobut-2-enedinitrile (1/1)." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (May 31, 2012): o1944. http://dx.doi.org/10.1107/s1600536812023264.

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In the crystal structure of the title compound, C11H26N3 +·Cl−·C4H4N4, the (2Z)-2,3-diaminobut-2-ene-dinitrile (Z-DAMN) molecules are connected with the chloride ions via N—H...Cl hydrogen bonds, forming ribbons running along the a axis. The guanidinium ions are located in between the ribbons formed by Z-DAMN molecules and chloride ions.

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43

Frank, Walter, and Guido J. Reiß. "Spezielle Alkylammoniumhexachlorometallate, III [1] Synthese und Kristallstruktur von Tris(guanidinium)- hexachlororhodat(III)-monohydrat, [C(NH2)3]3 [RhCl6] · H2O / Alkylammonium Hexachlorometallates, III [1] Synthesis, and Crystal Structure of Tris(guanidinium) Hexachlororhodate(III) Monohydrate, [C(NH2)3]3[RhCl6] · H2O." Zeitschrift für Naturforschung B 51, no. 10 (October 1, 1996): 1464–68. http://dx.doi.org/10.1515/znb-1996-1017.

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Tris(guanidinium) hexachlororhodate(III) monohydrate, [C(NH2)3]3[RhCl6] · H2O (1 ) has been obtained by the reaction of rhodium(III) chloride with guanidine hydrochloride in hydrochloric acid solution. 1 crystallizes in the triclinic space group P1̅ (a = 7.6013(9) Å, b = 8.6912(10) Å, c = 15.956(2) Å, α = 93.177(10)°, β = 101.691(10)°, γ = 113.995(9)°, V = 931.8(2), Z = 2). Two crystallographically independent hexachlororhodate ions, three crystallographically independent guanidinium ions and one water molecule are linked by a complex framework of hydrogen bonds.

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44

Kantlehner, Willi, Ioannis Tiritiris, Wolfgang Frey, and Ralf Kreß. "Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen." Zeitschrift für Naturforschung B 75, no. 6-7 (August 27, 2020): 685–95. http://dx.doi.org/10.1515/znb-2019-0230.

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AbstractBis[bis(dibutylamino)methylen]hydrazine 8 is prepared from N,N,N′,N′-tetrabutylchloroformamidinium chloride (4c) and hydrazine. Bromine transforms 8 to the heterocyclic guanidinium salt 15a which is isolated as tetraphenylborate. From N,N,N′,N′-tetraalkylchloroformamidiniumchlorides and ethylendiamine the diguanidines are prepared which are alkylated to give diguanidinium salts, From these salts guanidinium salts can be prepared by anion metathesis with tetraphenylborate-, iodide-, hexafluorphosphate-, trifluoromethansulfonat-, bis(trifluormethansulfonyl)imide and tricyanmethanide as counteranions. The structure of the compounds 15 and 17b is confirmed by crystal structure analyses.

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45

Leonarski, Filip, Monika Świniarska, and Andrzej Leś. "Asymmetric Behavior of Thymidylate Synthase Dimer Subunits in Denaturating Solvent Observed with Molecular Dynamics." Computational Biology Journal 2015 (March 11, 2015): 1–9. http://dx.doi.org/10.1155/2015/389018.

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A molecular dynamics simulations of the thymidylate synthase denaturation in chaotrope solvents (urea, guanidinium hydrochloride) were performed on 600 ns timescale. It appeared that this dimeric enzyme undergoes partial unfolding asymmetrically. It was shown also that urea is a better denaturant in the MD condition, as compared to guanidinium chloride. The unfolding occurs first at the external helices (AA 88-118) and follows by the AA 188-200 region. The present results correspond to the suggested in the literature activity of thymidylate synthase through a half-the-site mechanism.

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46

Vortman, M. Ya, Yu B. Pysmenna, A. I. Chuenko, A. V. Rudenko, V. V. Tretyak, V. N. Lemeshko, and V. V. Shevchenko. "Bactericidal and Fungicidal Activity of Polyetherguanidinium Chloride." Mikrobiolohichnyi Zhurnal 83, no. 1 (February 17, 2021): 49–57. http://dx.doi.org/10.15407/microbiolj83.01.049.

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There is information in the literature about the salts of polyhexamethylene guanidine (PGMG), which are effective biocidal and sterilizing drugs and disinfectants due to the wide range of their antimicrobial activity against gram-positive and gram-negative bacteria (including Mycobacterium tuberculosis), viruses, and fungi. The aim of this work is to study the bactericidal and fungicidal activity of the synthesized polyetherguanidinium chloride against a number of bacteria and microscopic fungi. Methods. Cultivation of microorganisms. Bacteria were grown on meat-peptone agar for 48 hours at a temperature of 28±2°C. Test cultures of micromycetes were cultured on beer wort agar (6°B), incubated for 14 days in a thermostat at a temperature of 28±2°C. Antimicrobial activity of newly synthesized polyetherguanidinium chloride was determined by standard disco-diffusion method, and fungicidal activity was determined by agar diffusion method. Results. The synthesis of polyetherguanidinium chloride was carried out in two stages. The first stage was the synthesis of a guanidinium-containing oligoether with terminal guanidine moieties by the reaction between an aromatic oligoepoxide and guanidine. The second stage was the synthesis of polyetherguanidinium chloride by the reaction between a guanidinium-containing oligoether with terminal guanidine moieties and oligooxyethylenediamine. The bactericidal and fungicidal activity of polyetherguanidinium chloride against various heterotrophic bacteria and microscopic fungi has been shown. It was found that polyetherguanidinium chloride at concentrations of 1–3% inhibited the growth of gram-negative (Escherichia coli 475, Klebsiella pneumonia 479) and gram-positive (Staphylococcus aureus 451) bacteria. The proposed 1% solution of polyetherguanidinium chloride shows a 1.5 times higher antimicrobial activity than the polymeric disinfectant polyhexamethyleneguanidinium chloride for E. coli 475 and K. pneumoniae 479 bacteria and lower antimicrobial activity for S. aureus 451 bacteria. According to the obtained data, it was noted that polyetherguanidinium chloride at a concentration of 1% had a high fungicidal activity against almost all investigated isolates: Aspergillus versicolor F-41250, Acremoneum humicola F-41252, Acremoneum roseum F-41251, Cladosporium sphaerospermum F-41255, Paecilomyces lilacinus F-41256 and Scopulariopsis candida F-41257. Conclusions. Received polyetherguanidinium chloride at a concentration of 1% showed bactericidal activity against S. aureus 451, E. coli 475, K. pneumoniae 479 and fungicidal effect to all fungi studied by us, and so can be used as a disinfectant for building materials.

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47

Sjöberg, P. O., M. Lindahl, J. Porath, and T. Wadström. "Purification and characterization of CS2, a sialic acid-specific haemagglutinin of enterotoxigenic Escherichia coli." Biochemical Journal 255, no. 1 (October 1, 1988): 105–11. http://dx.doi.org/10.1042/bj2550105.

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CS2 fimbriae of enterotoxigenic Escherichia coli were purified and characterized. The surface haemagglutinins (fimbriae) were detached by sonication from a strain producing only the CS2 fimbriae. Isolation was carried out by gel filtration on a Sepharose 4B column. After depolymerization, the fimbriae subunits were purified on a Sephacryl S-300 column in 8.0 M-guanidinium chloride. From 1 litre of medium, 4-6 mg of purified fimbriae was obtained. We found that CS2 fimbriae were completely dissociated by saturated guanidinium chloride into subunits with a molecular mass of 16.5 kDa. CS2 fimbriae was sialic acid-specific, since sialic acids were the most potent inhibitors, and neuraminidase treatment of erythrocytes abolished haemagglutination. Both fimbriae and fimbrial subunits were found to bind to bovine erythrocytes. The binding of subunits to erythrocytes could be inhibited with low concentrations of sialyl-lactose.

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48

Monterroso, Begoña, and Allen P. Minton. "Effect of High Concentration of Inert Cosolutes on the Refolding of an Enzyme." Journal of Biological Chemistry 282, no. 46 (September 18, 2007): 33452–58. http://dx.doi.org/10.1074/jbc.m705157200.

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The kinetics of refolding of carbonic anhydrase II following transfer from a buffer containing 5 m guanidinium chloride to a buffer containing 0.5 m guanidinium chloride were studied by measuring the time-dependent recovery of enzymatic activity. Experiments were carried out in buffer containing concentrations of two “inert” cosolutes, sucrose and Ficoll 70, a sucrose polymer, at concentrations up to 150 g/liter. Data analysis indicates that both cosolutes significantly accelerate the rate of refolding to native or compact near-native conformations, but decrease the fraction of catalytically active enzyme recovered in the limit of long time. According to the simplest model that fits the data, both cosolutes accelerate a competing side reaction yielding inactive compact species. Acceleration of the side reaction by Ficoll is significantly greater than that of sucrose at equal w/v concentrations.

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49

Sola-Penna, Mauro, and José Roberto Meyer-Fernandes. "Trehalose Protects Yeast Pyrophosphatase against Structural and Functional Damage Induced by Guanidinium Chloride." Zeitschrift für Naturforschung C 51, no. 3-4 (April 1, 1996): 160–64. http://dx.doi.org/10.1515/znc-1996-3-405.

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Abstract Trehalose is accumulated at very high concentrations in yeasts when this organism is sub mitted to a stress condition. This report approaches the question on the protective effect of trehalose and its degradation product, glucose, against structural and functional damage promoted by guanidinium on yeast cytosolic pyrophosphatase. Here it is shown that both, 1 ᴍ trehalose or 2 ᴍ glucose, are able to attenuate at almost the same extent the conforma tional changes promoted by guanidinium chloride on the pyrophosphatase structure. On the other hand, while 1 m trehalose increases 3.8 times the Ki (from 0.15 to 0.57 ᴍ) for guanidi nium chloride inhibition of pyrophosphatase activity, 2 m glucose did not even duplicate this parameter (from 0.15 to 0.25 ᴍ). These data support evidences for a functional reason for the accumulation by yeasts of trehalose, and not other compound, during stress conditions.

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50

Yu, Miao, Lijia Chen, Guannan Li, Cunyun Xu, Chuanyao Luo, Meng Wang, Gang Wang, et al. "Effect of guanidinium chloride in eliminating O2− electron extraction barrier on a SnO2 surface to enhance the efficiency of perovskite solar cells." RSC Advances 10, no. 33 (2020): 19513–20. http://dx.doi.org/10.1039/d0ra01501f.

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The charge transfer hindrance of adsorbed oxygen species on SnO₂ is successfully reduced by modifying it with guanidinium chloride, improving the power conversion efficiency from 15.33% to 18.46% (after modification) with maximum fill factor of 80%.

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