Non-enzymatic transamination and β-elimination ofDL-S-benzylcysteine catalysed by a potent pyridoxal model
- 1 January 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 3,p. 341-345
- https://doi.org/10.1039/p29850000341
Abstract
Non-enzymatic reactions of DL-S-benzylcysteine (2H) promoted by N-dodecylpyridoxal (1a) have been investigated in an aqueous hexadecyltrimethylammonium chloride (CTACI) micelle at 30.0 °C. The substrate undergoes mainly β-elimination at alkaline pH, whereas transamination with (1a) predominates in weakly acidic media. The kinetic α-deuterium isotope effects (kH/kD) of substrate were determined as 8.7 and 5.5 for β-elimination and transamination, respectively, at pH 7.0. These data indicate unambiguously that the rate-determining step of both reactions is the α-hydrogen abstraction from the reactive Schiff's base of substrate and (1a).Keywords
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