Document Detail


A chemo-enzymatic route to synthesize (S)-γ-valerolactone from levulinic acid.
MedLine Citation:
PMID:  23296499     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Levulinic acid is a feasible platform chemical derived from acid-catalyzed hydrolysis of lignocellulose. The conversion of this substrate to (S)-γ-valerolactone ((S)-GVL) was investigated in a chemo-enzymatic reaction sequence that benefits from mild reaction conditions and excellent enantiomeric excess of the desired (S)-GVL. For that purpose, levulinic acid was chemically esterified over the ion exchange resin Amberlyst 15 to yield ethyl levulinate (LaOEt). The keto ester was successfully reduced by (S)-specific carbonyl reductase from Candida parapsilosis (CPCR2) in a substrate-coupled cofactor regeneration system utilizing isopropanol as cosubstrate. In classical batch experiments, a maximum conversion of 95 % was achieved using a 20-fold excess of isopropanol. Continuous reduction of LaOEt was carried out for 24 h, and a productivity of more than 5 mg (S)-ethyl-4-hydroxypentanoate (4HPOEt) per μg CPCR2 was achieved. Afterwards (S)-4HPOEt (>99%ee) was substituted to lipase-catalyzed lactonization using immobilized lipase B from Candida antarctica to yield (S)-GVL in 90 % overall yield and >99%ee.
Authors:
Katharina Götz; Andreas Liese; Marion Ansorge-Schumacher; Lutz Hilterhaus
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Publication Detail:
Type:  Journal Article     Date:  2013-01-08
Journal Detail:
Title:  Applied microbiology and biotechnology     Volume:  97     ISSN:  1432-0614     ISO Abbreviation:  Appl. Microbiol. Biotechnol.     Publication Date:  2013 May 
Date Detail:
Created Date:  2013-04-16     Completed Date:  2013-10-21     Revised Date:  2014-03-18    
Medline Journal Info:
Nlm Unique ID:  8406612     Medline TA:  Appl Microbiol Biotechnol     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  3865-73     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Alcohol Oxidoreductases / metabolism
Candida / enzymology
Lactones / chemistry*,  metabolism*
Levulinic Acids / chemistry*,  metabolism*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Lactones; 0/Levulinic Acids; EC 1.1.-/Alcohol Oxidoreductases; EC 1.1.1.21/carbonyl reductase (NADPH); O7056XK37X/gamma-valerolactone

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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