THIOLYSIS OF Nim‐2, 4‐DINITROPHENYL‐HISTIDINE PEPTIDES WITH 2‐MERCAPTOETHANOL
- 12 January 1978
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 11 (1), 1-8
- https://doi.org/10.1111/j.1399-3011.1978.tb02814.x
Abstract
The thiolysis of Nim-2, 4-dinitrophenyl-histidine peptides with 2-mercaptoethanol demonstrates an optimal rate between pH 8.5 and 9.0. Base lability of both reactants and product was investigated as a possible cause for the pH optimum. N-2, 4-Dinitrophenylimidazole, a model for Nim-2, 4-dinitrophenyl-histidine peptides, 2-mercaptoethanol and the product of thiolysis, 2, 4-dinitrophenyl-S-mercaptoethan-2-ol, were subjected to aqueous basic conditions (pH 8.5 to 12.0). The reactions were followed spectrophotometrically, and products were identified by comparison of their ultra-violet spectra with commercially available or synthetic compounds. Mechanisms and rate constants for base hydrolysis of 2, 4-dinitrophenyl-thio ethers are presented. Although N-2, 4-dinitrophenylimidazole and 2, 4-dinitrophenyl-S-mercaptoethan-2-ol dohydrolyze, it is the oxidation of 2-mercaptoethanol to 2-mercaptoethanol disulfide which results in the decreasing rate of thiolysis above pH 9.0.Keywords
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