Title
Synthesis and biological evaluation of novel gramicidin s analogues
Author
Tuin, A.W.
Palachanis, D.K.
Buizert, A.
Grotenbreg, G.M.
Spalburg, E.
de Neeling, A.J.
Mars-Groenendijk, R.H.
Noort, D.
van der Marel, G.A.
Overkleeft, H.S.
Overhand, M.
TNO Defensie en Veiligheid
Publication year
2009
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 These derivatives contain a modified turn region in which the DPhe-Pro motif has been replaced by a constrained furanoid sugar amino acid or a flexible linear aminoethoxy acetic acid moiety.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.
Subject
Chemistry
Antibiotics
Conformation analysis
Peptidomimetics
Sugar amino acid
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DOI
https://doi.org/10.1002/ejoc.200900460
TNO identifier
183954
ISSN
1434-193X
Source
European Journal of Organic Chemistry (25), 4231-4241
Document type
article