Synthesis of ethyl-(3 R,5 S)-dihydroxy-6-benzyloxyhexanoates via diastereo- and enantioselective microbial reduction: Cloning and expression of ketoreductase III from Acinetobacter sp. SC 13874
Previously we have demonstrated the reduction of ethyl and t-butyl diketoesters 1 to the corresponding syn-(3 R,5 S)-dihydroxy esters 2a by Acinetobacter sp. 13874. The syn-(3 R,5 S)-dihydroxy ester 2a was obtained with an enantiomeric excess (e.e.) of 99% and a diastereomeric excess (de) of 63%. In...
Saved in:
Published in | Enzyme and microbial technology Vol. 43; no. 7; pp. 544 - 549 |
---|---|
Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Amsterdam
Elsevier Inc
10.12.2008
Elsevier |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Summary: | Previously we have demonstrated the reduction of ethyl and
t-butyl diketoesters
1 to the corresponding syn-(3
R,5
S)-dihydroxy esters
2a by
Acinetobacter sp. 13874. The
syn-(3
R,5
S)-dihydroxy ester
2a was obtained with an enantiomeric excess (e.e.) of 99% and a diastereomeric excess (de) of 63%. In this report, we identified a gene encoding desired ketoreductase III which catalyzed the diastereoselective reduction of diketoesters
1 to
syn-(3
R,5
S)-dihydroxy esters
2a and describe cloning and expression of ketoreductase III into
Escherichia coli. Cells or extracts of recombinant
E. coli efficiently reduced the diketoester
1 to the corresponding
syn-(3
R,5
S)-dihydroxy ester
2a in 99.3% yield, 100% e.e., and 99.8% de. |
---|---|
Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0141-0229 1879-0909 |
DOI: | 10.1016/j.enzmictec.2008.07.005 |