Lanthionine macrocyclization by in situ activation of serine

J Pept Res. 1998 Jun;51(6):432-6. doi: 10.1111/j.1399-3011.1998.tb00641.x.

Abstract

The present report details a straightforward, solid-phase approach to cyclolanthionine peptides. After stepwise assembly of the linear sequence and transformation of a single exposed serine to bromoalanine using P(Ph)3/CBr4, the detritilation of a cysteine side-chain sets the stage for a base-promoted macrocyclization. The entire procedure can be carried out in a solid-phase vessel using conventional 9-fluorenylmethyloxycarbonyl/tert-butyl-based chemistry and is amenable to automated format. The utility of this novel procedure is demonstrated by the synthesis of two previously reported lanthionine-containing cyclic peptides.

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemistry
  • Amino Acids, Cyclic / chemistry*
  • Chromatography, High Pressure Liquid
  • Molecular Structure
  • Sequence Analysis
  • Serine / chemistry*
  • Sulfides

Substances

  • Amino Acids, Cyclic
  • Sulfides
  • Serine
  • lanthionine
  • Alanine