Issue 7, 2007

A concise stereoselective synthesis of orthogonally protected lanthionine and β-methyllanthionine

Abstract

Lantibiotics such as nisin are active against most Gram-positive bacteria and constitute an important class of antibacterial agents. These ribosomally synthesized peptides contain either one or both of the unusual amino acids meso-lanthionine (m-Lan) or β-methyllanthionine (β-MeLan). Nucleophilic ring opening of sulfamidates allows facile preparation of stereochemically pure derivatives of m-Lan and β-MeLan with orthogonal protection for solid phase synthesis of lantibiotic analogues.

Graphical abstract: A concise stereoselective synthesis of orthogonally protected lanthionine and β-methyllanthionine

Supplementary files

Article information

Article type
Paper
Submitted
13 Dec 2006
Accepted
26 Jan 2007
First published
07 Feb 2007

Org. Biomol. Chem., 2007,5, 1031-1038

A concise stereoselective synthesis of orthogonally protected lanthionine and β-methyllanthionine

S. L. Cobb and J. C. Vederas, Org. Biomol. Chem., 2007, 5, 1031 DOI: 10.1039/B618178C

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