Synthesis of epimers of L-cyclopentenylglycine using enzymatic resolution.

Abstract:

:Both epimers of the naturally occurring nonproteinogenic amino acid L-cyclopentenylglycine, (2S,1'S)- and (2S, 1'R)-2-(cyclopent-2'-enyl)glycine, were obtained via a procedure involving condensation of 3-chlorocyclopentene with diethyl acetylaminomalonate, deethoxycarbonylation, chromatographic separation of the resulting two pairs of enantiomers, and enzymatic resolution of the racemates employing enantioselective hydrolysis of the ethyl ester group with alpha-chymotrypsin. The method was used for preparation of (13)C-labeled compounds of interest for biosynthetic tracer experiments. Enantiomeric purity of the products was determined by chiral HPLC on a Crownpak CR(+) column. The biologically active (2S,1'R) isomer was obtained as a pure compound and characterized for the first time. The (2R,1'R) and (2R,1'S) isomers were obtained as N-acetyl ethyl ester derivatives.

journal_name

Chirality

journal_title

Chirality

authors

Andersen L,Nielsen B,Jaroszewski JW

doi

10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;

subject

Has Abstract

pub_date

2000-10-01 00:00:00

pages

665-9

issue

9

eissn

0899-0042

issn

1520-636X

pii

10.1002/1520-636X(2000)12:9<665::AID-CHIR4>3.0.CO;

journal_volume

12

pub_type

杂志文章