Title
Ring-extended gramicidin S analogs Containing cis δ-sugar amino acid turn mimetics with varying ring size
Author
Knijnenburg, A.D.
Spalburg, E.
de Neeling, A.J.
Mars-Groenendijk, R.H.
Noort, D.
Grotenbreg, G.M.
van der Marel, G.A.
Overkleeft, H.S.
Overhand, M.
Publication year
2012
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.
Subject
Life
CBRN - CBRN Protection
EELS - Earth, Environmental and Life Sciences
Defence Research
Defence, Safety and Security
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
To reference this document use:
http://resolver.tudelft.nl/uuid:5b1f7a7d-243b-4624-9a73-1ece82d378c5
DOI
https://doi.org/10.1002/hlca.201200497
TNO identifier
470048
ISSN
0018-019X
Source
Helvetica Chimica Acta, 95 (12), 2544-2561
Bibliographical note
Chemicals/CAS: amino acid, 65072-01-7; gramicidin S, 113-73-5, 15207-30-4, 17174-97-9, 57572-76-6; ornithine, 70-26-8, 7006-33-9
Document type
article