Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria, Ed. Polifunzionale, 87036, Arcavacata di Rende, Italy
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Org. Biomol. Chem., 2013,11, 3786-3796
25 Jan 2013,
11 Apr 2013
First published online
12 Apr 2013
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.
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Organic & Biomolecular Chemistry
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