TY - JOUR PY - 1998// TI - Synthesis of the suicide substrate D-propargylglycine stereospecifically labelled with deuterium and investigation of its oxidation by D-amino acid oxidase JO - Journal of the Chemical Society - Perkin Transactions 1 A1 - Church, N.J. A1 - Young, D.W. SP - 1475 EP - 1482 VL - IS - 9 N2 - 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 a key step in the formation of this compound.

Language: en

LA - en SN - 0300-922X UR - http://dx.doi.org/10.1039/a800579f ID - ref1 ER -