Lanthionine macrocyclization by in situ activation of serine
- 1 June 1998
- journal article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 51 (6) , 432-436
- https://doi.org/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.Keywords
This publication has 26 references indexed in Scilit:
- Unique peptide modifications involved in the biosynthesis of lantibioticsTrends in Biotechnology, 1995
- Biosynthesis and Biological Activities of Lantibiotics with Unique Post‐Translational ModificationsEuropean Journal of Biochemistry, 1995
- Biosynthesis and Biological Activities of Lantibiotics with Unique Post-Translational ModificationsEuropean Journal of Biochemistry, 1995
- New application of peptide cyclization on an oxime resin (the PCOR method): preparation of lanthionine peptidesJournal of the Chemical Society, Chemical Communications, 1993
- TheMitsunobu ReactionPublished by Wiley ,1992
- CONSTRAINED PEPTIDES: MODELS OF BIOACTIVE PEPTIDES AND PROTEIN SUBSTRUCTURESAnnual Review of Biochemistry, 1992
- Conformational restrictions of biologically active peptides via amino acid side chain groupsLife Sciences, 1982
- Synthesis and some biological activities of analogues of deamino-vasopressin with the disulphide bridge altered to a thioether bridgeCollection of Czechoslovak Chemical Communications, 1974
- Structure and synthesis of dihydroxypentyluracil from bacteriophage SP-15 deoxyribonucleic acidJournal of the American Chemical Society, 1973
- Preparation and mass spectral properties of cystine and lanthionine derivatives. Novel synthesis of L-lanthionine by selective desulfurizationThe Journal of Organic Chemistry, 1971