Journal
CHEMCATCHEM
Volume 11, Issue 11, Pages 2600-2606Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201900382
Keywords
Asymmetric reduction; directed evolution; chiral lactones; carbonyl reductase; biocatalysis
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Funding
- National Key Research and Development Program of China [2016YFA0204300]
- National Natural Science Foundation of China [21536004, 21776085, 21871085]
- Natural Science Foundation of Shanghai [18ZR1409900, 18DZ1112703]
- Fundamental Research Funds for the Central Universities [22221818014, 222201714026, WF1714026]
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Structurally diverse gamma- and delta-lactones were efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500-fold) and thermostability toward 14 gamma-/delta-keto acids and esters, compared with the wild-type enzyme, with 110-fold enhancement in catalytic efficiency (k(cat)/K-m) toward methyl 4-oxodecanoate. The preparative synthesis of alkyl and aromatic gamma- and delta-lactones with 95 %->99 % ee and 78 %-90 % yields was demonstrated. The highest space-time yield, 1175 g L-1 d(-1), was achieved for (R)-gamma-decalactone.
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