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Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones
Author(s) -
MartinezRojas Enriqueta,
Olejniczak Teresa,
Neumann Konrad,
Garbe LeifAlexander,
Boratyñski Filip
Publication year - 2016
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22623
Subject(s) - chemistry , yield (engineering) , diol , moiety , decane , chirality (physics) , enantiomeric excess , biocatalysis , enantiomer , organic chemistry , rhodococcus , catalysis , stereochemistry , enantioselective synthesis , reaction mechanism , materials science , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , metallurgy , quark , enzyme
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 γ‐ ( 2b ) and δ‐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 . © 2016 Wiley Periodicals, Inc.