We report here a convenient and simple solid-phase synthesis of N-nosyl-N-methyl-α-amino acids and N-Fmoc-N-methyl-α-amino acids, important building blocks for the synthesis of conformationally restricted and protease-resistant natural peptides and peptide analogues. The methodology involves the use of 2-chlorotrityl chloride resin to temporarily protect the carboxylic group of α-amino acids and of diazomethane as the reagent to methylate the sulfonamidic function. The approach developed is particularly efficient also with α-amino acids bearing appropriately protected functionalized side chains.

Solid Phase Synthesis of N-Nosyl- and N-Fmoc-N-Methyl-α-Amino Acids

DI GIOIA Maria Luisa;Leggio Antonella;
2007

Abstract

We report here a convenient and simple solid-phase synthesis of N-nosyl-N-methyl-α-amino acids and N-Fmoc-N-methyl-α-amino acids, important building blocks for the synthesis of conformationally restricted and protease-resistant natural peptides and peptide analogues. The methodology involves the use of 2-chlorotrityl chloride resin to temporarily protect the carboxylic group of α-amino acids and of diazomethane as the reagent to methylate the sulfonamidic function. The approach developed is particularly efficient also with α-amino acids bearing appropriately protected functionalized side chains.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/20.500.11770/129485
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