Access to Enantiomerically Pure cis- and trans-β-Phenylproline by High-Performance Liquid Chromatography Resolution

被引：7

作者：

Fatas, Paola ^{[1
]}

Gil, Ana M. ^{[1
]}

Isabel Calaza, M. ^{[1
]}

Jimenez, Ana I. ^{[1
]}

Cativiela, Carlos ^{[1
]}

机构：

[1] Univ Zaragoza, CSIC, Dept Quim Organ, ISQCH, E-50009 Zaragoza, Spain

来源：

CHIRALITY | 2012年 / 24卷 / 12期

关键词：

proline analog; phenylalanine analog; polysaccharide-derived chiral stationary phase; chiral HPLC; HPLC enantioseparation; 3-SUBSTITUTED PROLINE DERIVATIVES; CHIRAL STATIONARY-PHASE; CONSTRAINED AMINO-ACIDS; HPLC RESOLUTION; ANTIGEN PRESENTATION; EFFICIENT RESOLUTION; CYCLOPROPANE ANALOG; CYCLOHEXANE ANALOGS; MICHAEL ADDITION; STEREOISOMERS;

D O I：

10.1002/chir.22101

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The preparation of all four stereoisomers of the proline analog that bears a phenyl group attached to the beta carbon either cis or trans to the carboxylic acid (cis- and trans-beta-phenylproline, respectively) has been addressed. The methodology developed allows access to multigram quantities of the target amino acids in enantiomerically pure form and suitably protected for use in peptide synthesis. Racemic precursors of cis-beta-phenylproline and trans-beta-phenylproline were prepared from easily available starting materials and subjected to high-performance liquid chromatography enantioseparation. Semipreparative columns (250?x?20?mm) containing chiral stationary phases based on amylose (Chiralpak IA) (Daicel-Chiral Technologies Europe, Illkirch, France) or cellulose (Chiralpak IC) were used respectively for the resolution of the cis- and trans-beta-phenylproline precursors. Chirality, 24:1082-1091, 2012. (c) 2012 Wiley Periodicals, Inc.

引用

页码：1082 / 1091

页数：10

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