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

article








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.
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.
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Antimicrobial activityConformational analysisGramicidin SPeptidesAnti-microbial activityConformational analysisGramicidin SMimeticsOxetanesProtonatedRing sizesSide-chainsSugar amino acidsPeptidesSugarsAmino acidsAmino acidFuran derivativeGramicidin derivativeGramicidin SGramicidin s derivativeHemolytic agentOrnithineOxetane derivativePyran derivativeUnclassified drugAntibacterial activityBiomimeticsControlled studyDrug synthesisGram negative bacteriumGram positive bacteriumHmolysisHumanHuman cellHydrophobicityMinimum inhibitory concentrationMolecular sizeNonhumanPriority journalProton transportStructure activity relation
TNO Identifier
470048
Repository link
https://resolver.tno.nl/uuid:5b1f7a7d-243b-4624-9a73-1ece82d378c5
ISSN
0018-019X
Source
Helvetica Chimica Acta, 95(12), pp. 2544-2561.
Pages
2544-2561
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