Expansion of Phosphane Treasure Box for Staudinger Peptide Ligation

A smooth traceless ligation strategy using an air-stable phosphane probe (2-(diphenylphosphanyl)­phenyl)­methanol as a C-terminus activator has been demonstrated at simple and sterically hindered amino acid junctions (Gly, Ala, Trp, Glu). This Staudinger peptide ligation proceeds via formation of a...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2020-10, Vol.85 (19), p.12147-12159
Main Authors: Bajaj, Kiran, Pillai, Girinath G, Sakhuja, Rajeev, Kumar, Dalip
Format: Article
Language:English
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:A smooth traceless ligation strategy using an air-stable phosphane probe (2-(diphenylphosphanyl)­phenyl)­methanol as a C-terminus activator has been demonstrated at simple and sterically hindered amino acid junctions (Gly, Ala, Trp, Glu). This Staudinger peptide ligation proceeds via formation of a seven-membered transition state to afford di-, tetra-, and pentapeptides in 78–95% yields. The experimental results of ligation at Gly junction and regioselective ligation at Glu junction were theoretically studied by computational calculations. These findings established the versatile behavior of our synthesized phosphane probe for Staudinger peptide ligation toward synthesizing peptides and proteins of choice.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01319