A proline-based phosphine template for Staudinger ligation

Chung-Min Park; Wei Niu; Chunrong Liu; Tyler D Biggs; Jiantao Guo; Ming Xian

doi:10.1021/ol3022484

A proline-based phosphine template for Staudinger ligation

Org Lett. 2012 Sep 7;14(17):4694-7. doi: 10.1021/ol3022484. Epub 2012 Aug 27.

Authors

Chung-Min Park¹, Wei Niu, Chunrong Liu, Tyler D Biggs, Jiantao Guo, Ming Xian

Affiliation

¹ Department of Chemistry, Washington State University, Pullman, Washington 99164, USA.

PMID: 22924811
DOI: 10.1021/ol3022484

Abstract

A proline-based phosphine template enabling a rapid Staudinger ligation of azide-containing substrates under mild conditions is reported. This reaction has a second-order rate constant of 1.12 M(-1) s(-1). It is expected that the proline-based Staudinger ligation strategy will be a useful method for bioconjugation and proline based peptide coupling.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Azides / chemistry
Chemistry, Organic / methods*
Combinatorial Chemistry Techniques
Molecular Structure
Peptides / chemistry
Proline / analogs & derivatives*
Proline / chemistry*

Substances

Azides
Peptides
Proline