Biocatalytic Promiscuity of Lipases in Carbon‐Phosphorus Bond Formation. Issue 10 (23rd April 2019)

• Record Type: Journal Article
• Authors: Koszelewski, Dominik; Ostaszewski, Ryszard
• Is Part Of: ChemCatChem. Volume 11:Issue 10(2019)
• Page Start: 2554
• Page End: 2558
• Publication Date: 2019-04-23
• Subjects: Pudovik-Abramov reaction -- α-hydroxy phosphonates -- promiscuity -- hydrolases -- biocatalysis; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201900397
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: 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. Abstract : Party PPL ! Promiscuous lipase‐catalyzed carbon‐phosphorus bond formation is presented. The developed enzymatic Pudovik‐Abramov reaction of various aromatic and aliphatic aldehydes and dialkyl phosphonates provides biologically and pharmacologically relevant α‐hydroxy phosphonates with the yields up to 85 %. PPL: Porcine pancreas lipase