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Ring‐Extended Gramicidin S Analogs Containing cis δ ‐Sugar Amino Acid Turn Mimetics with Varying Ring Size
Author(s) -
Knijnenburg Annemiek D.,
Spalburg Emile,
de Neeling Albert J.,
MarsGroenendijk Roos H.,
Noort Daan,
Grotenbreg Gijsbert M.,
van der Marel Gijs A.,
Overkleeft Herman S.,
Overhand Mark
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200497
Subject(s) - chemistry , gramicidin s , stereochemistry , ring (chemistry) , residue (chemistry) , protonation , oxetane , sugar , turn (biochemistry) , gramicidin , side chain , amino acid , organic chemistry , biochemistry , ion , membrane , polymer
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.