Issue 23, 2013
From the journal:

Organic & Biomolecular Chemistry

C → N and N → C solution phase peptide synthesis using the N-acyl 4-nitrobenzenesulfonamide as protection of the carboxylic function†

Rosaria De Marco,a   Mariagiovanna Spinella,a   Anna De Lorenzo,a   Antonella Leggio*a  and  Angelo Liguori*a  

* Corresponding authors

a Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria, Ed. Polifunzionale, 87036, Arcavacata di Rende, Italy
E-mail: a.liguori@unical.it
Fax: +39 0984 493265
Tel: +39 0984 493205

Abstract

In this paper we describe a solution phase peptide synthesis strategy using the 4-nitrobenzenesulfonamido/N-methyl-4-nitrobenzenesulfonamido group as a protecting/activating system of the carboxyl function. The 4-nitrobenzenesulfonamido group is stable during peptide chain elongation (Fmoc chemistry). The N-aminoacyl or N-dipeptidyl-4-nitrobenzensulfonamides, when activated by methylation, can be easily coupled with another amino acid or reconverted into the free-carboxyl function amino acids or peptides. This activatable protecting group allows both the C → N and the N → C direction solution phase peptide synthesis. We also verified that the absolute configuration at the chiral centers does not change during the coupling reactions.

Graphical abstract: C → N and N → C solution phase peptide synthesis using the N-acyl 4-nitrobenzenesulfonamide as protection of the carboxylic function

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3OB40169C
Article type
Paper
Submitted
25 Jan 2013
Accepted
11 Apr 2013
First published
12 Apr 2013

Org. Biomol. Chem., 2013,11, 3786-3796

Permissions

Request permissions

C → N and N → C solution phase peptide synthesis using the N-acyl 4-nitrobenzenesulfonamide as protection of the carboxylic function

R. De Marco, M. Spinella, A. De Lorenzo, A. Leggio and A. Liguori, Org. Biomol. Chem., 2013, 11, 3786 DOI: 10.1039/C3OB40169C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements