Issue 15, 2010

Nitroneprotecting groups for enantiopure N-hydroxyamino acids: synthesis of N-terminal peptide hydroxylamines for chemoselective ligations

Abstract

The synthesis of enantiopure N-benzylidene nitrones of N-hydroxy-α-amino acids and their incorporation using standard Fmoc-based peptide chemistry into solid-supported peptide chains is described. Deprotection and resin cleavage affords N-terminal peptide hydroxylamines, which are the key substrates for chemoselective ligations with C-terminal peptide α-ketoacids. This general route is applicable to a variety of different N-terminal residues and provides a general approach to the solid phase synthesis of peptide hydroxylamines.

Graphical abstract: Nitrone protecting groups for enantiopure N-hydroxyamino acids: synthesis of N-terminal peptide hydroxylamines for chemoselective ligations

Supplementary files

Article information

Article type
Paper
Submitted
19 Mar 2010
Accepted
13 May 2010
First published
22 Jun 2010

Org. Biomol. Chem., 2010,8, 3405-3417

Nitrone protecting groups for enantiopure N-hydroxyamino acids: synthesis of N-terminal peptide hydroxylamines for chemoselective ligations

S. I. Medina, J. Wu and J. W. Bode, Org. Biomol. Chem., 2010, 8, 3405 DOI: 10.1039/C004490C

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