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
This publication has 23 references indexed in Scilit:
- Studies of the Synthetic Model Enzyme. The Synthesis of Cyclo(His–Glu–Cys-d-Phe–Gly)2 as the Esterase ModelBulletin of the Chemical Society of Japan, 1973
- Bridging of peptides to solid supports through the dinitrophenylene moiety. Bidirectional extension of peptide chainsJournal of the American Chemical Society, 1972
- Use of Nim-dinitrophenylhistidine in the solid-phase synthesis of the tricosapeptides 124-146 of human hemoglobin .beta. chainBiochemistry, 1969
- Thiolysis of some dinitrophenyl derivatives of amino acidsBiochemical and Biophysical Research Communications, 1967
- Chemical Interactions between Lysine and Dehydroalanine in Modified Bovine Pancreatic RibonucleaseJournal of the American Chemical Society, 1964
- Nim-2,4-dinitrophenyl-l-histidinBiochimica et Biophysica Acta (BBA) - General Subjects, 1964
- Cleavage of Histidyl Peptide Bonds by N-BromosuccinimideJournal of the American Chemical Society, 1963
- The Reaction of p-Nitrophenyl Acetate with ThiolsJournal of the American Chemical Society, 1962
- Reactivity of Nucleophilic Reagents toward EstersJournal of the American Chemical Society, 1960
- The Acid Strength of the -SH Group in Cysteine and Related CompoundsJournal of the American Chemical Society, 1955