title: Optical resolution and absolute configuration of N-benzyloxycarbonyl-alpha-alkoxyglycines
abstract: Optical resolution of racemic N-benzyloxycarbonyl-protected alpha-alkoxyglycines, (+/-)-Cbz-Gly(OR)-OH (R = Et and Pr(i)), was achieved by means of fractional crystallization of diastereomeric salts with (+)-(1S,2S)-2-amino-1-phenyl-1,3-propanediol or diastereomeric esters of (+)- or (-)-menthol. The D- and L-configurations were assigned to the (+)- and (-)-Cbz-Gly(OR)-OH, respectively, based on L-enantioselective enzymatic hydrolysis of (+/-)-Cbz-Gly(OR)-OR' (R = Me, Et, and Pr(i); R' = CH(2)CF(3) and Me) using porcine pancreatic lipase and papain. Chiroptical properties and HPLC retention times of D- and L-Gly(OR)-residue (R = Me and Pr(i))-containing peptides were compared in relation to their configurational assignments. Copyright 1999 Wiley-Liss, Inc.
authors.affiliation: Department of Applied Chemistry, Nagoya Institute of Technology, Showa-ku, Nagoya 466-8555, Japan.
authors.initials: M
authors.lastname: Kawai
authors.initials: K
authors.lastname: Yamada
authors.initials: K
authors.lastname: Hosoda
authors.initials: Y
authors.lastname: Omori
authors.initials: S
authors.lastname: Kato
authors.initials: N
authors.lastname: Nagayama
authors.initials: S
authors.lastname: Masui
authors.initials: M
authors.lastname: Kamiya
authors.initials: H
authors.lastname: Yamamura
authors.initials: S
authors.lastname: Araki
authors.initials: Y
authors.lastname: Butsugan