Issue 20, 2003

Enzymatic synthesis of phosphocarnitine, phosphogabob and fosfomycin

Abstract

Phosphocarnitine was conveniently obtained from easily available diethyl 3-chloro-2-oxopropanephosphonates, followed by subsequent reduction, Mucor miehei lipase (IM) mediated resolution, amination and dealkylation. Candida antarctica lipase B (CALB) served as an effective biocatalyst in the resolution of several 1- or 2- hydroxyalkanephosphonates. The chlorine atom in different positions on the molecules greatly affected their enantioselectivity. CALB also showed satisfactory enantioselectivity toward those molecules bearing an azido moiety. Both enantiomers of phosphogabob and fosfomycin were also prepared via CALB-mediated resolution as the key step.

Graphical abstract: Enzymatic synthesis of phosphocarnitine, phosphogabob and fosfomycin

Article information

Article type
Paper
Submitted
04 Jul 2003
Accepted
01 Sep 2003
First published
17 Sep 2003

Org. Biomol. Chem., 2003,1, 3564-3569

Enzymatic synthesis of phosphocarnitine, phosphogabob and fosfomycin

K. Wang, Y. Zhang and C. Yuan, Org. Biomol. Chem., 2003, 1, 3564 DOI: 10.1039/B307638P

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