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J Pept Sci. 2011 Mar;17(3):211-7. doi: 10.1002/psc.1314. Epub 2010 Oct 25.

Synthesis, biological activity and solution structure of new analogues of the antimicrobial Gramicidin S.

Author information

1
University of Gdańsk, Faculty of Chemistry, Sobieskiego 18, Gdańsk, 80-952, Poland. kamysz@chem.univ.gda.pl

Abstract

Gramicidin S (GS) is a cyclo-decapeptide antibiotic isolated from Bacillus brevis. The structural studies have shown that GS forms a two-stranded antiparallel β-sheet imposed by two II' β-turns. Despite its wide Gram+ and Gram- antimicrobial spectrum, GS is useless in therapy because of its high hemotoxicity in humans. It was found, however, that the analogues of GS-14 (GS with 14 amino acid residues) attained a better antimicrobial selectivity when their amphipatic moments were perturbed. In this study, we report effects of similar perturbations imposed on GS cyclo-decapeptide analogues. Having solved their structures by NMR/molecular dynamics and having tested their activities/selectivities, we have concluded that the idea of perturbation of the amphipatic moment does not work for GS-10_0 analogues. An innovative approach to the synthesis of head-to-tail cyclopeptides was used.

PMID:
21308877
DOI:
10.1002/psc.1314
[Indexed for MEDLINE]

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