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Biooxidation of Primary Alcohols to Aldehydes through Hydrogen Transfer Employing Janibacter terrae
Author(s) -
Orbegozo Thomas,
de Vries Johannes G.,
Kroutil Wolfgang
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000260
Subject(s) - chemistry , primary (astronomy) , allylic rearrangement , acetaldehyde , substituent , alcohol , solvent , biocatalysis , organic chemistry , acceptor , substrate (aquarium) , alcohol oxidation , hydrogen , primary alcohol , combinatorial chemistry , catalysis , ethanol , reaction mechanism , physics , oceanography , astronomy , geology , condensed matter physics
Chemoselective oxidations still represent a challenge for chemists. Lyophilized cells of Janibacter terrae were employed for the chemoselective oxidation of primary alcohols to the corresponding aldehydes by hydrogen transfer with the use of acetaldehyde as the hydrogen acceptor. Secondary alcohol moieties were transformed at a much slower rate. The substrate spectrum encompasses substituted benzyl alcohols, whereby substrates with a substituent in the meta position were well tolerated, whereas only very small substituents were tolerated in the ortho position. Furthermore, n ‐alkanols and allylic alcohols were transformed with good conversions. The biocatalyst was compatible with DMSO as a water miscible organic solvent up to 30 % v/v.