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Structural and biological evaluation of some loloatin C analogues

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Author: Tuin, A.W. · 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:Bioorganic and Medicinal Chemistry, 17, 17, 6233-6240
Identifier: 183955
doi: doi:10.1016/j.bmc.2009.07.049
Keywords: Chemistry · Cationic antimicrobial peptide · Loloatin C · Structure-activity relationship · Sugar amino acid

Abstract

Loloatin C is a cyclic cationic antimicrobial peptide which is active against Gram positive as well as certain Gram negative bacteria. Unfortunately, it is equally potent against human erythrocytes. To probe the structure-activity relationship of this promising antibiotic peptide, amino acid substitution and/or incorporation of a constraint sugar amino acid dipeptide isoster has been applied. Six new derivatives have been synthesized using SPPS and their solution structure investigated using NMR studies. Finally, the antimicrobial and the hemolytic activities have been determined. © 2009 Elsevier Ltd. All rights reserved.