Title
Exploring the conformational and biological versatility of ß-turn-modified gramicidin s by using sugar amino acid homologues that vary in ring size
Author
Knijnenburg, A.D.
Tuin, A.W.
Spalburg, E.
de Neeling, A.J.
Mars-Groenendijk, R.H.
Noort, D.
Otero, J.M.
Llamas-Saiz, A.L.
van Raaij, M.J.
van der Marel, G.A.
Overkleeft, H.S.
Overhand, M.
Publication year
2011
Abstract
Monobenzylated sugar amino acids (SAAs) that differ in ether ring size (containing an oxetane, furanoid, and pyranoid ring) were synthesized and incorporated in one of the ß-turn regions of the cyclo-decapeptide gramicidin S (GS). CD, NMR spectroscopy, modeling, and X-ray diffraction reveal that the ring size of the incorporated SAA moieties determines the spatial positioning of their cis-oriented carboxyl and aminomethyl substituents, thereby subtly influencing the amide linkages with the adjacent amino acids in the sequence. Unlike GS itself, the conformational behavior of the SAA-containing peptides is solvent dependent. The derivative containing the pyranoid SAA is slightly less hydrophobic and displays a diminished haemolytic activity, but has similar antimicrobial properties as GS. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Subject
Life
CBRN - CBRN Protection
EELS - Earth, Environmental and Life Sciences
Chemistry
ß-turn
Amino acids
Antimicrobial peptides
Conformation analysis
Gramicidin S
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DOI
https://doi.org/10.1002/chem.201002895
TNO identifier
428815
ISSN
0947-6539
Source
Chemistry - A European Journal, 17 (14), 3995-4004
Document type
article