The dimethylsulfoxonium methylide is described as a unique and useful reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-alpha-amino acid and N-Fmoc-peptide esters. The new methodology was applied successfully both to solution- and solid-phase peptide synthesis. The adopted methodology was extended successfully also to peptides containing amino acids bearing acid-sensitive protecting group in side chains. Furthermore no measurable epimerization was observed in the deprotection reaction of N-Fmoc-dipeptide methyl esters with dimethylsulfoxonium methylide. (C) 2013 Elsevier Ltd. All rights reserved.

The dimethylsulfoxonium methylide as unique reagent for the simultaneous deprotection of amino and carboxyl function on N-Fmoc-alfa - amino acid and N-Fmoc-peptide esters / Liguori, Angelo; Belsito, E. L.; De Marco, R.; Spinella, M.. - In: TETRAHEDRON. - ISSN 0040-4020. - 69:8(2013), pp. 2010-2016.

The dimethylsulfoxonium methylide as unique reagent for the simultaneous deprotection of amino and carboxyl function on N-Fmoc-alfa - amino acid and N-Fmoc-peptide esters

LIGUORI, Angelo;Leggio A.;
2013

Abstract

The dimethylsulfoxonium methylide is described as a unique and useful reagent for the simultaneous deprotection of amino and carboxyl function of N-Fmoc-alpha-amino acid and N-Fmoc-peptide esters. The new methodology was applied successfully both to solution- and solid-phase peptide synthesis. The adopted methodology was extended successfully also to peptides containing amino acids bearing acid-sensitive protecting group in side chains. Furthermore no measurable epimerization was observed in the deprotection reaction of N-Fmoc-dipeptide methyl esters with dimethylsulfoxonium methylide. (C) 2013 Elsevier Ltd. All rights reserved.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/142293
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