Optical resolution and absolute configuration of N-Benzyloxycarbonyl-α-alkoxyglycines

✍ Scribed by Masao Kawai; Keiichi Yamada; Kouji Hosoda; Yasuhiro Omori; Shuji Kato; Nobuhiro Nagayama; Seigo Masui; Masao Kamiya; Hatsuo Yamamura; Shuki Araki; Yasuo Butsugan

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 129 KB
• Volume: 11
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1999)11:7<561::aid-chir8>3.0.co;2-1

✦ Synopsis

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.