Kinetically Controlled Chemoselective Cyclization Simplifies the Access to Cyclic and Branched Peptides

A bis­(2-sulfanylethyl)­amido group reacts significantly faster with cysteinyl peptides when installed on the C-terminal end of a peptide in comparison with the side-chain of Asp and Glu. This property enabled the design of a kinetically controlled chemoselective peptide cyclization reaction, giving...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 18; no. 15; pp. 3842 - 3845
Main Authors Boll, Emmanuelle, Drobecq, Hervé, Lissy, Elizabeth, Cantrelle, François-Xavier, Melnyk, Oleg
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.08.2016
Amer Chemical Soc
Subjects
Analytical chemistry
Chemical Sciences
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BACKBONE CYCLIZATION
CONTROLLED LIGATION
HYDRAZIDES
SURROGATES
AFFINITY
STABILITY
STRATEGY
PROTEIN CHEMICAL-SYNTHESIS
THIOESTERS
SCAFFOLDS
Online AccessGet full text

Cover

More Information
Summary:A bis­(2-sulfanylethyl)­amido group reacts significantly faster with cysteinyl peptides when installed on the C-terminal end of a peptide in comparison with the side-chain of Asp and Glu. This property enabled the design of a kinetically controlled chemoselective peptide cyclization reaction, giving straightforward access to cyclic and branched peptides in one pot.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01847