4.3 Article

Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

Journal

CHIRALITY
Volume 28, Issue 9, Pages 623-627

Publisher

WILEY-BLACKWELL
DOI: 10.1002/chir.22623

Keywords

Bacteria; diols; lactones; oxidation; Rhodococcus erythropolis DSM 44534; stereoselectivity

Funding

  1. National Science Centre [2011/03/B/NZ9/05005]

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In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding - (2b) and -decalactones (3b) with yield of 80% and enantiomeric excess (ee)=75% and ee=90%, respectively. Among oxidation of meso diols, (-)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee=76% as well as (-)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee=90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623-627, 2016. (c) 2016 Wiley Periodicals, Inc.

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