Peptide transformation leading to peptide-peptidosulfonamide hybrids and oligo peptidosulfonamides

Liskamp, R.M.J. and Kruijtzer, J.A.W. (2004) Peptide transformation leading to peptide-peptidosulfonamide hybrids and oligo peptidosulfonamides. Molecular Diversity, 8(2), pp. 79-87. (doi: 10.1023/B:MODI.0000025651.88080.9d)

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The sulfonamide moiety was introduced as a potential transition state isostere of the hydrolysis of the amide bond. Subsequently, the increased acidity of a sulfonamide N-H as compared to a regular amide N-H was explored in the development of peptidosulfonamide synthetic receptor molecules for binding and catalysis. The required building blocks for these compounds were accessible via an efficient synthesis, which also enabled the synthesis of oligopeptidosulfonamides as well as peptidosulfonamide-betapeptide hybrids. The structural consequences of the introduction of the peptidosulfonamide residues were studied and were further explored by the synthesis of cyclic peptidosulfonamides e.g. by ring-closing metathesis.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Liskamp, R.M.J., and Kruijtzer, J.A.W.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Molecular Diversity
ISSN (Online):1573-501X

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