Issue 17, 2009

Application of carbodiimide mediated Lossen rearrangement for the synthesis of α-ureidopeptides and peptidylureas employing N-urethane α-amino/peptidyl hydroxamic acids

Abstract

Application of the Lossen rearrangement to the synthesis of N-urethane protected α-peptidyl ureas and ureidopeptides is reported. The carbodiimide mediated rearrangement of N-Boc/Z/Fmoc protected α-amino/peptide hydroxamic acids into isocyanates and coupling of the latter with the amino acid esters/peptide esters have been accomplished in a single-pot to obtain good yields of urea products. Synthesis of the ureidoalanine derivatives via the hydroxamate derivatives of N-protected aspartic acid has also been carried out using the same procedure.

Graphical abstract: Application of carbodiimide mediated Lossen rearrangement for the synthesis of α-ureidopeptides and peptidyl ureas employing N-urethane α-amino/peptidyl hydroxamic acids

Supplementary files

Article information

Article type
Paper
Submitted
24 Mar 2009
Accepted
20 May 2009
First published
07 Jul 2009

Org. Biomol. Chem., 2009,7, 3520-3526

Application of carbodiimide mediated Lossen rearrangement for the synthesis of α-ureidopeptides and peptidyl ureas employing N-urethane α-amino/peptidyl hydroxamic acids

N. Narendra, G. Chennakrishnareddy and V. V. Sureshbabu, Org. Biomol. Chem., 2009, 7, 3520 DOI: 10.1039/B905790K

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