Synthesis of the suicide substrate D-propargylglycine stereospecifically labelled with deuterium and investigation of its oxidation by D-amino acid oxidase 1

NJ Church, DW Young

Index: Church, Nicola J.; Young, Douglas W. Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 9 p. 1475 - 1482

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Citation Number: 14

Abstract

Stereospecifically deuteriated samples of D-propargylglycine 1 have been prepared by reaction of the labelled Pmc-protected aziridine free acids 22 with a lithium acetylide followed by deprotection. These samples have been used to show that D-amino acid oxidase, in converting D-propargylglycine to the lactone 5, deprotonates C-3 in a non- stereospecific manner. This strongly supports the idea that non-enzymic deprotonation is ...