A chemo-enzymatic route to synthesize ( S)-γ-valerolactone from levulinic acid

Götz, Katharina; Liese, Andreas; Ansorge-Schumacher, Marion; Hilterhaus, Lutz
May 2013
Applied Microbiology & Biotechnology;May2013, Vol. 97 Issue 9, p3865
Academic Journal
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.


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