Synthesis of (-)-lobeline via enzymatic desymmetrization of lobelanidine

Robert Chênevert; Pierre Morin

doi:10.1016/j.bmc.2009.01.055

Synthesis of (-)-lobeline via enzymatic desymmetrization of lobelanidine

Bioorg Med Chem. 2009 Mar 1;17(5):1837-9. doi: 10.1016/j.bmc.2009.01.055. Epub 2009 Jan 31.

Authors

Robert Chênevert¹, Pierre Morin

Affiliation

¹ Département de Chimie, PROTEO, Faculté des Sciences et de Génie, Université Laval, Québec, Canada. robert.chenevert@chm.ulaval.ca

PMID: 19217305
DOI: 10.1016/j.bmc.2009.01.055

Abstract

The bioactive alkaloid (-)-lobeline was synthesized via the stereoselective acylation (desymmetrization) of meso-lobelanidine by vinyl acetate in the presence of Candida antarctica lipase B.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biocatalysis
Fungal Proteins
Lipase / chemistry
Lobeline / analogs & derivatives*
Lobeline / chemical synthesis*
Lobeline / chemistry
Stereoisomerism

Substances

Fungal Proteins
Lobeline
Lipase
lipase B, Candida antarctica
lobelanidine