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Issue 23, 2013
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CN and NC solution phase peptide synthesis using the N-acyl 4-nitrobenzenesulfonamide as protection of the carboxylic function

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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 CN and the NC 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

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Publication details

The article was received on 25 Jan 2013, accepted on 11 Apr 2013 and first published on 12 Apr 2013


Article type: Paper
DOI: 10.1039/C3OB40169C
Citation: Org. Biomol. Chem., 2013,11, 3786-3796
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    CN and NC 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

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