STEREOCHEMISTRY OF CONVERSION OF THE SUICIDE SUBSTRATES BETA-CHLORO-D-ALANINE AND D-SERINE AND L-SERINE O-SULFATES INTO PYRUVATE BY D-AMINO-ACID AMINOTRANSFERASE AND BY L-ASPARTATE AMINOTRANSFERASE
Bs. Axelsson et al., STEREOCHEMISTRY OF CONVERSION OF THE SUICIDE SUBSTRATES BETA-CHLORO-D-ALANINE AND D-SERINE AND L-SERINE O-SULFATES INTO PYRUVATE BY D-AMINO-ACID AMINOTRANSFERASE AND BY L-ASPARTATE AMINOTRANSFERASE, Journal of the Chemical Society. Perkin transactions. I, (15), 1994, pp. 2137-2142
beta-Chloro-D-alanine and D-serine O-sulfate are converted into a puta
tive aminoacrylate intermediate by D-amino acid aminotransferase. This
either reacts with pyridoxal phosphate to form a reactive inhibitor o
f the enzyme or it is protonated and hydrolysed to give pyruvate. The
protonation reaction is shown to occur with modest stereoselectivity.
indicating overall retention of stereochemistry in replacement of the
leaving group by hydrogen. The corresponding reaction of L-serine O-su
lfate using L-aspartate aminotransferase shows little or no stereosele
ctivity.