Exploring the Conformational and Biological Versatility of β-Turn-Modified Gramicidin S by Using Sugar Amino Acid Homologues that Vary in Ring Size
Monobenzylated sugar amino acids (SAAs) that differ in ether ring size (containing an oxetane, furanoid, and pyranoid ring) were synthesized and incorporated in one of the β‐turn regions of the cyclo‐decapeptide gramicidin S (GS). CD, NMR spectroscopy, modeling, and X‐ray diffraction reveal that the...
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Published in | Chemistry : a European journal Vol. 17; no. 14; pp. 3995 - 4004 |
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Main Authors | , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Weinheim
WILEY-VCH Verlag
28.03.2011
WILEY‐VCH Verlag Wiley |
Subjects | |
Online Access | Get full text |
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Summary: | Monobenzylated sugar amino acids (SAAs) that differ in ether ring size (containing an oxetane, furanoid, and pyranoid ring) were synthesized and incorporated in one of the β‐turn regions of the cyclo‐decapeptide gramicidin S (GS). CD, NMR spectroscopy, modeling, and X‐ray diffraction reveal that the ring size of the incorporated SAA moieties determines the spatial positioning of their cis‐oriented carboxyl and aminomethyl substituents, thereby subtly influencing the amide linkages with the adjacent amino acids in the sequence. Unlike GS itself, the conformational behavior of the SAA‐containing peptides is solvent dependent. The derivative containing the pyranoid SAA is slightly less hydrophobic and displays a diminished haemolytic activity, but has similar antimicrobial properties as GS.
Ring size matters: Monobenzylated sugar amino acids (SAAs) that differ in ether ring size (containing an oxetane, furanoid, and pyranoid ring, see scheme) are synthesized and incorporated in one of the β‐turn regions of the cyclo‐decapeptide gramicidin S (GS). The pyranoid SAA derivative is slightly less hydrophobic and interestingly it displays a diminished haemolytic activity, but has similar antimicrobial properties to GS. |
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Bibliography: | Xunta de Galicia - No. BFU2008-01588 Leiden Institute of Chemistry ark:/67375/WNG-WD5JSTMF-C istex:A18166280ECC1F6A458D197C52B92D8A2468CAE8 ArticleID:CHEM201002895 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0947-6539 1521-3765 |
DOI: | 10.1002/chem.201002895 |