SYNTHESIS OF THE SUICIDE SUBSTRATE D-PROPARGYLGLYCINE STEREOSPECIFICALLY LABELED WITH DEUTERIUM AND INVESTIGATION OF ITS OXIDATION BY D-AMINO-ACID OXIDASE

Stereospecifically deuteriated samples of D-propargylglycine 1 have be en prepared by reaction of the labelled Pmc-protected aziridine free a cids 22 with a lithium acetylide followed by deprotection. These sampl es have been used to show that D-amino acid oxidase, in converting D-p ropargylglycine to the lactone 5, deprotonates C-3 in a non-stereospec ific manner. This strongly supports the idea that non-enzymic deproton ation is a key step in the formation of this compound.