SYNTHESIS OF TRIPEPTIDE INHIBITORS OF PEPTIDYLGLYCINE ALPHA-AMIDATINGMONOOXYGENASE (PAM) CONTAINING D-STYRYLGLYCINE AND L-STYRYLGLYCINE

Both enantiomers of (E)- and (Z)-2-amino-4-phenyl-3-butenoic acids (st yrylglycines) 11a,b and 12a,b, were synthesised in non-racemic form, i n 7 steps starting from either- or L-aspartic acid. (E)-Styrylglycine 11a was converted to the tripeptide D-Phe-L-Phr-D-styrylglycine 15, an d also to three diastereomeric tripeptides 16-18. All four tripeptides , and both enantiomers of N-acetylstyryl-glycine 13a and 13b, were tes ted as inhibitors of peptidylglycine alpha-amidating monooxygenase (PA M). (C) 1997 Elsevier Science Ltd.