Synthesis of tripeptide inhibitors of peptidylglycine alpha-amidating monooxygenase (PAM) containing D- and L-styrylglycine

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