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Ring-extended derivatives of gramicidin S with furanoid sugar amino acids in the turn region have enhanced antimicrobial activity

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Author: Knijnenburg, A.D. · Spalburg, E. · Neeling, A.J. de · Mars-Groenendijk, R.H. · Noort, D. · Grotenbreg, G.M. · Marel, G.A. van der · Overkleeft, H.S. · Overhand, M.
Type:article
Date:2009
Institution: TNO Defensie en Veiligheid
Source:ChemMedChem, 12, 4, 1976-1979
Identifier: 275971
doi: doi:10.1002/cmdc.200900379
Keywords: Defence · β turns · Antibiotics · Cyclic peptides · Gramicidin S · Sugar amino acids

Abstract

(Chemical Equation Presented) A series of ring-extended gramicidin S (GS) derivatives containing furanoid sugar amino acids were evaluated. Although the extended GS derivatives have a less well-defined secondary structure as determined by NMR and CD, some derivatives show an improved biological profile, namely, an increased antibacterial activity and decreased hemolytic activity. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.