Ring‐Extended Gramicidin S Analogs Containing cis δ‐Sugar Amino Acid Turn Mimetics with Varying Ring Size |
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Authors: | Annemiek D Knijnenburg Emile Spalburg Albert J de Neeling Roos H Mars‐Groenendijk Daan Noort Gijsbert M Grotenbreg Gijs A van der Marel Herman S Overkleeft Mark Overhand |
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Institution: | 1. Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, NL‐2300 RA Leiden, (fax: +31715274307);2. National Institute of Public Health and the Environment, Laboratory for Infectious Diseases, P.O. Box 1, NL‐3720 BA Bilthoven;3. TNO, Prins Maurits Laboratory, P.O. Box 45, NL‐2280 AA Rijswijk |
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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. |
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Keywords: | Gramicidin S Antimicrobial activity Conformational analysis Peptides |
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