Synthesis and Biological Evaluation of Novel Gramicidin S Analogues (Eur. J. Org. Chem. 25/2009)

The cover picture shows the cationic antimicrobial peptide Gramicidin S (GS, left structure), which disrupts the bacterial membrane, however with little selectivity over the erythrocytic membrane. This mode of action is explained by the amphiphilic β‐sheet structure of GS. Three new analogues of GS...

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Published in:European journal of organic chemistry 2009-09, Vol.2009 (25), p.4187-4187
Main Authors: Tuin, Adriaan Willem, Palachanis, Dimitrios Konstantinos, Buizert, Annelies, Grotenbreg, Gijsbert Marnix, Spalburg, Emile, de Neeling, Albert J., Mars-Groenendijk, Roos H., Noort, Daan, van der Marel, Gijsbert A., Overkleeft, Herman S., Overhand, Mark
Format: Article
Language:English
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Summary:The cover picture shows the cationic antimicrobial peptide Gramicidin S (GS, left structure), which disrupts the bacterial membrane, however with little selectivity over the erythrocytic membrane. This mode of action is explained by the amphiphilic β‐sheet structure of GS. Three new analogues of GS were designed in which one DPhe‐Pro β‐turn motif has been replaced by different sugar amino acids (1, 2 and 3 in the right structures). The solution structures of these new analogues were assessed by 1D and 2D NMR spectroscopy, which shows a slightly altered backbone conformation. The antibacterial and hemolytic activities of all analogues were also determined in this study. Details are discussed in the article by M. Overhand et al. on p. 4231 ff.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200990069