Synthesis of stereospecifically labelled D-prop-2-ynylglycine and investigation of the action of D-amino acid oxidase

Abstract

Stereospecifically deuteriated samples of D-prop-2-ynylglycine 1 are synthesised by reaction of the labelled aziridines 13 with a carbon nucleophile followed by deprotection; incubation of these samples with D-amino acid oxidase indicates that, in formation of the lactone 5, deprotonation at C-3 is non-stereospecific, strongly supporting non-enzymatic deprotonation as a key step in the formation of this compound.