title: C → N and N → C solution phase peptide synthesis using the N-acyl 4-nitrobenzenesulfonamide as protection of the carboxylic function.
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.
authors: Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria, Ed. Polifunzionale, 87036, Arcavacata di Rende, Italy.
authors: Rosaria
authors: R
authors: De Marco
authors: Mariagiovanna
authors: M
authors: Spinella
authors: Anna
authors: A
authors: De Lorenzo
authors: Antonella
authors: A
authors: Leggio
authors: Angelo
authors: A
authors: Liguori
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D009578:Nitrobenzenes / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D012996:Solutions
chemical_list: D002264:Carboxylic Acids; D009578:Nitrobenzenes; D010455:Peptides; D012996:Solutions; D002244:Carbon; C036077:nitrobenzene; D009584:Nitrogen