- Stereochemical Analysis of γ-Replacement and γ-Elimination Processes Catalyzed by a Pyridoxal Phosphate Dependent Enzyme
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(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.
- Chang, Michael N. T.,Walsh, Christopher T.
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