73703-25-0Relevant articles and documents
Stereochemical Analysis of γ-Replacement and γ-Elimination Processes Catalyzed by a Pyridoxal Phosphate Dependent Enzyme
Chang, Michael N. T.,Walsh, Christopher T.
, p. 4921 - 4927 (1981)
(Z)- and (E)-Vinylglycine samples have been synthesized and used to determine the stereochemical outcome of a pyridoxal phosphate dependent bacterial enzyme cyctathionine γ-synthase.For the first time both the γ-replacement mode, vinylglycine or O-succinylhomoserine to cystathionine, and the γ-elimination mode, vinylglycine or O-succinylhomoserine to α-ketobutyrate, have been solved stereochemically.The diastereomeric cyctathionines produces enzymically in the γ-replacement mode were degraded to homoserines, the absolute chiralities were determined, and then the compounds were succinilated.The O-succinylhomoserines were then processed enzymically to cystathionines enzymically, and the stereochemical course of the first half-reaction was thereby determined.
