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Synthesis and Biological Evaluation of Novel Gramicidin S Analogues (Eur. J. Org. Chem. 25/2009)
Author(s) -
Tuin Adriaan Willem,
Palachanis Dimitrios Konstantinos,
Buizert Annelies,
Grotenbreg Gijsbert Marnix,
Spalburg Emile,
de Neeling Albert J.,
MarsGroenendijk Roos H.,
Noort Daan,
van der Marel Gijsbert A.,
Overkleeft Herman S.,
Overhand Mark
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200990069
Subject(s) - chemistry , gramicidin s , cationic polymerization , gramicidin , peptide , stereochemistry , amphiphile , nuclear magnetic resonance spectroscopy , selectivity , antibacterial peptide , membrane , mode of action , cyclic peptide , antibacterial activity , combinatorial chemistry , biochemistry , organic chemistry , bacteria , polymer , copolymer , catalysis , biology , genetics
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 Three new analogues of GS were designed in which one D Phe‐Pro β‐turn motif has been replaced by different sugar amino acids ( 1 , 2 and 3 in the right structures).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.