Enzymatic Resolution of 1-Phenylethanol and Formation of a Diastereomer: An Undergraduate 1H NMR Experiment To Introduce Chiral Chemistry

被引：7

作者：

Faraldos, Juan A. ^{[1
]}

Giner, Jose-Luis ^{[1
]}

Smith, David H. ^{[2
]}

Wilson, Mark ^{[2
]}

Ronhovde, Kyla ^{[2
]}

Wilson, Erin ^{[2
]}

Clevette, David ^{[2
]}

Holmes, Andrea E. ^{[2
]}

Rouhier, Kerry ^{[3
]}

机构：

[1] SUNY ESF, Dept Chem, Syracuse, NY 13210 USA

[2] Doane Coll, Dept Chem, Crete, NE 68333 USA

[3] Kenyon Coll, Dept Chem, Gambier, OH 43022 USA

来源：

JOURNAL OF CHEMICAL EDUCATION | 2011年 / 88卷 / 03期

基金：

美国国家科学基金会;

关键词：

Second-Year Undergraduates; Laboratory Instruction; Organic Chemistry; Collaborative/Cooperative Learning; Hands-On Learning/Manipulatives; Chirality/Optical Activity; Diastereomers; Stereochemistry; Enzymes; NMR Spectroscopy; KINETIC RESOLUTION; SECONDARY ALCOHOLS; ORGANIC-CHEMISTRY; ACYLASE; REDUCTION; PROJECT; YEAST; DERIVATIVES; HYDROLYSIS; MANDELATE;

D O I：

10.1021/ed100325p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This organic laboratory experiment introduces students to stereoselective enzyme reactions, resolution of enantiomers, and NMR analysis of diastereomers. The reaction between racemic 1-phenylethanol and vinyl acetate in hexane to form an ester is catalyzed by acylase I. The unreacted alcohol is then treated with a chiral acid and the resulting ester diastereomer is analyzed by NMR. This experiment is suitable for group work in the laboratory as several diastereomers are synthesized and compared to determine which enantiomer of 1-phenylethanol reacts with the enzyme.

引用

页码：334 / 336

页数：3

共 27 条

[1] Enantiomeric resolution wof (±)-mandelic acid by (1R,2S)-(-)-ephedrine [J].