The mechanism of inactivation of penicillin by cysteine and other mercaptoamines.

作者: Karl Ford Nakken , Lorentz Eldjarn , Alexander Pihl

DOI: 10.1016/0006-2952(60)90025-3

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摘要: Abstract The kinetics of penicillin inactivation by various mercaptoamines have been followed polarimetry. In the case primary mereaptoamines reactions are second order with respect to time and concentration reactants. By determining appropriate rate constants under different conditions pH ionic strength conclusion is reached that limiting step a bimolecular reaction involving mercaptide ion. mechanism probably involves formation semimercaptol. Several possible mechanisms for role amino group in opening β-lactam ring discussed. tertiary mercaptoamine N:N-dimethylcysteamine nearly follows first gives as end product partially racemized penicilloic acid.

参考文章(11)
Fritz Lipmann, L.Constanc. Tuttle, A SPECIFIC MICROMETHOD FOR THE DETERMINATION OF ACYL PHOSPHATES Journal of Biological Chemistry. ,vol. 159, pp. 21- 28 ,(1945) , 10.1016/S0021-9258(19)51298-4
Lorentz Eldjarn, Karl F. Nakken, Alexander Pihl, K. E. Almin, Arne Magnéli, Herbert Pestmalis, Stig Åsbrink, The Interaction of Cysteamine and Cysteine with various Carbonyl Compounds. Acta Chemica Scandinavica. ,vol. 11, pp. 1085- 1086 ,(1957) , 10.3891/ACTA.CHEM.SCAND.11-1085B
Bertil Hansen, Åke Hanngren, Olof Theander, Margareta Zackrisson, L. Ernster, E. Diczfalusy, Kinetics of the Hydrolytic Cleavage of Organic Protolytes. Acta Chemica Scandinavica. ,vol. 12, pp. 324- 331 ,(1958) , 10.3891/ACTA.CHEM.SCAND.12-0324
E. A. Moelwyn-Hughes, The Kinetics of Reactions in Solutions. The Journal of Physical Chemistry. ,vol. 38, pp. 854- 855 ,(1933) , 10.1021/J150357A018
C. J. CAVALLITO, J. H. BAILEY, PRELIMINARY NOTE ON THE INACTIVATION OF ANTIBIOTICS Science. ,vol. 100, pp. 390- 390 ,(1944) , 10.1126/SCIENCE.100.2600.390
S. Gabriel, Ernst Leupold, Zur Kenntniss einiger Abkömmlinge des Bromäthyl‐ und Brompropyl‐Amins European Journal of Inorganic Chemistry. ,vol. 31, pp. 2832- 2839 ,(1898) , 10.1002/CBER.18980310344
Alexander Pihl, Lorentz Eldjarn, Karl F. Nakken, K. Hartiala, S. Veige, E. Diczfalusy, The Nucleophilic Reactivity of Biological Thiols with Respect to Thiol-Disulphide Exchange Reactions. Acta Chemica Scandinavica. ,vol. 12, pp. 1357- 1357 ,(1958) , 10.3891/ACTA.CHEM.SCAND.12-1357
Ruth E. Benesch, Reinhold Benesch, The Acid Strength of the -SH Group in Cysteine and Related Compounds Journal of the American Chemical Society. ,vol. 77, pp. 5877- 5881 ,(1955) , 10.1021/JA01627A030
R. O. Clinton, U. J. Salvador, S. C. Laskowski, C. M. Suter, Sulfur-containing amines; local anesthetics. Journal of the American Chemical Society. ,vol. 70, pp. 950- 955 ,(1949) , 10.1021/JA01183A018
Nancy Atkinson, Neville F Stanley, Antibacterial Substances produced by Moulds. 4. The Detection and Occurrence of Suppressors ol Penicidin Activity. Immunology and Cell Biology. ,vol. 21, pp. 249- 253 ,(1943) , 10.1038/ICB.1943.34