Biomimetic Stereoselective Formation of Methyllanthionine

Fmoc-(2R,3S)-3-methyl-Se-phenylselenocysteine was used for the synthesis of dehydrobutyrine (Dhb)-containing peptides. Biomimetic cyclization via Michael addition of Cys to a Dhb yielded the B-ring of the lantibiotic subtilin as a single diastereomer. The methyllanthionine product was shown to have...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2002-04, Vol.4 (8), p.1335-1338
Main Authors: Zhou, Hao, van der Donk, Wilfred A
Format: Article
Language:English
Subjects:
Alanine - analogs & derivatives
Alanine - chemical synthesis
Anti-Bacterial Agents - chemical synthesis
Chromatography, High Pressure Liquid
Cyclization
Fluorenes
Indicators and Reagents
Magnetic Resonance Spectroscopy
Stereoisomerism
Sulfides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Fmoc-(2R,3S)-3-methyl-Se-phenylselenocysteine was used for the synthesis of dehydrobutyrine (Dhb)-containing peptides. Biomimetic cyclization via Michael addition of Cys to a Dhb yielded the B-ring of the lantibiotic subtilin as a single diastereomer. The methyllanthionine product was shown to have the natural configuration by preparation of the authentic stereoisomer. The formation of a single isomer suggests that the prepeptide has a strong intrinsic preference for the stereochemistry observed in lantibiotics.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol025629g