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Synthesis and biological evaluation of novel gramicidin s analogues

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Author: Tuin, A.W. · Palachanis, D.K. · Buizert, A. · Grotenbreg, G.M. · Spalburg, E. · Neeling, A.J. de · Mars-Groenendijk, R.H. · Noort, D. · Marel, G.A. van der · Overkleeft, H.S. · Overhand, M.
Type:article
Date:2009
Institution: TNO Defensie en Veiligheid
Source:European Journal of Organic Chemistry, 25, 4231-4241
Identifier: 183954
doi: doi:10.1002/ejoc.200900460
Keywords: Chemistry · Antibiotics · Conformation analysis · Peptidomimetics · Sugar amino acid

Abstract

The synthesis of three new analogues of the cyclic cationic antimicrobial peptide Gramicidin S is described. These derivatives contain a modified turn region in which the DPhe-Pro motif has been replaced by a constrained furanoid sugar amino acid or a flexible linear aminoethoxy acetic acid moiety. Structural analysis revealed conformational changes in the modified turn region compared to GS. The biological profile of these compounds however resembles that of Gramicidin S and previously described analogues. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.