Facile ring-opening of N-acylisatins for the development of novel peptidomimetics

A range of novel mono- and bis-glyoxylamide peptidomimetics were prepared via the facile ring-opening of N-acylisatins with amino acids and peptide derivatives. The ring-opening of N-acylisatins with dipeptides and tripeptides was discovered to be the most efficient strategy for the synthesis of sec...

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Bibliographic Details
Published in:Tetrahedron 2011-09, Vol.67 (39), p.7603-7610
Main Authors: Cheah, Wai Ching, Wood, Kasey, Black, David StC, Kumar, Naresh
Format: Article
Language:English
Subjects:
Amino acids
Chemistry
Derivatives
Exact sciences and technology
Glyoxylamides
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
N-acylisatins
Organic chemistry
Peptides
Peptidomimetics
Preparations and properties
Strategy
Synthesis (chemistry)
Tetrahedrons
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Summary:A range of novel mono- and bis-glyoxylamide peptidomimetics were prepared via the facile ring-opening of N-acylisatins with amino acids and peptide derivatives. The ring-opening of N-acylisatins with dipeptides and tripeptides was discovered to be the most efficient strategy for the synthesis of second and third generation glyoxylamides. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2011.07.036