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Ring-extended gramicidin S analogs Containing cis δ-sugar amino acid turn mimetics with varying ring size

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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:2012
Source:Helvetica Chimica Acta, 12, 95, 2544-2561
Identifier: 470048
doi: doi:10.1002/hlca.201200497
Keywords: Antimicrobial activity · Conformational analysis · Gramicidin S · Peptides · Anti-microbial activity · Conformational analysis · Gramicidin S · Mimetics · Oxetanes · Protonated · Ring sizes · Side-chains · Sugar amino acids · Peptides · Sugars · Amino acids · Amino acid · Furan derivative · Gramicidin derivative · Gramicidin S · Gramicidin s derivative · Hemolytic agent · Ornithine · Oxetane derivative · Pyran derivative · Unclassified drug · Antibacterial activity · Biomimetics · Controlled study · Drug synthesis · Gram negative bacterium · Gram positive bacterium · Hmolysis · Human · Human cell · Hydrophobicity · Minimum inhibitory concentration · Molecular size · Nonhuman · Priority journal · Proton transport · Structure activity relation · Defence Research · Defence, Safety and Security · Life · CBRN - CBRN Protection · EELS - Earth, Environmental and Life Sciences

Abstract

This article presents a series of ring-extended gramicidin S derivatives, 9-14, that have four ornithine residues as polar protonated side chains and one modified turn region containing a mono-functionalized cis-δ-oxetane, δ-furanoid, or δ-pyranoid sugar amino acid residue. Of the GS analogs evaluated, we identified compound 7, which contains the mono-benzyloxy cis-δ-pyranoid sugar amino acid, as having a better biological profile than the clinically applied topical antibiotic gramicidin S. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.