PMID: 9650717Jul 3, 1998Paper

Lanthionine macrocyclization by in situ activation of serine

The Journal of Peptide Research : Official Journal of the American Peptide Society
J P MayerM A Jarosinski

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.

References

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Citations

Sep 4, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·John S Davies
Sep 20, 2012·Angewandte Chemie·Aline Dantas de AraujoPaul F Alewood
Feb 20, 2016·Chemical Communications : Chem Comm·Ellen C GleesonAndrea J Robinson
Nov 14, 2000·Organic Letters·Z Miao, J P Tam
Oct 11, 2003·The Journal of Organic Chemistry·M Firouz Mohd MustapaAlethea B Tabor
Apr 13, 2002·Organic Letters·Hao Zhou, Wilfred A van der Donk

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