A biomimetic approach to lanthionines

Org Lett. 2012 Jan 6;14(1):334-7. doi: 10.1021/ol203068s. Epub 2011 Dec 16.

Abstract

The asymmetric sulfa-Michael additions of appropriately protected L- and D-cysteine derivatives to new chiral dehydroamino acid derivatives have been developed as key steps in the synthesis of biologically important cysteine derivatives, such as lanthionine (Lan) and β-methyllanthionine (MeLan), which are unusual bis-α-amino acids found in the emerging lantibiotics such as nisin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Amino Acids / chemistry
  • Biomimetic Materials / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism
  • Sulfides / chemical synthesis*

Substances

  • Amino Acids
  • Sulfides
  • lanthionine
  • Alanine