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Biocatalytic Promiscuity of Lipases in Carbon‐Phosphorus Bond Formation
Author(s) -
Koszelewski Dominik,
Ostaszewski Ryszard
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900397
Subject(s) - chemistry , furfural , organic chemistry , biocatalysis , lipase , catalysis , carbon fibers , enzyme catalysis , enzyme , reaction mechanism , materials science , composite number , composite material
A promiscuous lipase‐catalyzed carbon‐phosphorus bond formation is presented. The developed enzymatic Pudovik‐Abramov reaction of various aromatic and aliphatic aldehydes with dialkyl phosphonates provides biologically and pharmacologically relevant α‐hydroxy phosphonates with the yields from 11 % to 85 %. The developed protocol proceeds in the presence of porcine pancreas lipase under environmentally sustainable conditions. The influence of the reaction conditions including enzyme origin, organic solvent, and temperature on the reaction course was examined. The developed protocol is applicable to a range of aldehydes, including synthetically relevant heterocyclic furfural and 2‐thiophenecarbaldehyde.