Catalytic removal of N-allyloxycarbonyl groups using the [CpRu(IV)(pi-C3H5)(2-quinolinecarboxylato)]PF6 complex. A new efficient deprotecting method in peptide synthesis

Shinji Tanaka; Hajime Saburi; Takanori Murase; Masahiro Yoshimura; Masato Kitamura

doi:10.1021/jo060445r

Catalytic removal of N-allyloxycarbonyl groups using the [CpRu(IV)(pi-C3H5)(2-quinolinecarboxylato)]PF6 complex. A new efficient deprotecting method in peptide synthesis

J Org Chem. 2006 Jun 9;71(12):4682-4. doi: 10.1021/jo060445r.

Authors

Shinji Tanaka¹, Hajime Saburi, Takanori Murase, Masahiro Yoshimura, Masato Kitamura

Affiliation

¹ Research Center for Materials Science and Department of Chemistry, Nagoya University, Japan.

PMID: 16749807
DOI: 10.1021/jo060445r

Abstract

A variety of amines including even sterically less demanding and highly nucleophilic secondary amines have been efficiently deprotected without decarboxylative N-allylation from the corresponding N-allyloxycarbonyl (N-AOC) compounds by using a catalytic amount of [CpRu(IV)(pi-C3H5)(2-quinolinecarboxylato)]PF6 in the presence of 1 molar amount of trifluoromethanesulfonic acid, the general utility of which has been demonstrated by the efficient synthesis of a collagen protein unit tripeptide, Pro-Pro-Gly.

Publication types

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

MeSH terms

Amines / chemistry
Catalysis
Collagen
Methods
Oligopeptides / chemical synthesis*
Peptides / chemical synthesis*

Substances

Amines
Oligopeptides
Peptides
prolyl-prolyl-glycine
Collagen