Ring‐Extended Gramicidin S Analogs Containing  cis δ ‐Sugar Amino Acid Turn Mimetics with Varying Ring Size | Zendy

Knijnenburg Annemiek D. | Zendy; Spalburg Emile | Zendy; de Neeling Albert J. | Zendy; MarsGroenendijk Roos H. | Zendy; Noort Daan | Zendy; Grotenbreg Gijsbert M. | Zendy; van der Marel Gijs A. | Zendy; Overkleeft Herman S. | Zendy; Overhand Mark | Zendy

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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.

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