Synthesis of individual glutamate-containing phosphonamidothionate stereoisomers

The acquisition of the individual stereoisomers of chiral phosphonothioic a cids is anticipated to reveal the significance of phosphorus stereochemistr y upon the inhibition of metallocarboxypeptidases as well as their utility as chiral and stereoselective inhibitory probes. Two methods for preparing individual glutamate-containing phosphonamidothioic acid diastereomers have been identified. One method achieves the resolution through fractional cry stallization of the intermediate 9-fluorenemethoxy phosphonamidates while t he second does so through chromatographic resolution of intermediate beta-( acylmercapto)ethyl phosphonamidothiolates. (C) 2001 Elsevier Science Ltd. A ll rights reserved.