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dc.contributor.authorvan Raaij, Mark J.-
dc.contributor.authorOverhand, Mark-
dc.date.accessioned2012-07-10T10:26:21Z-
dc.date.available2012-07-10T10:26:21Z-
dc.date.issued2010-
dc.identifierdoi: 10.1002/chem.200902984-
dc.identifierissn: 0947-6539-
dc.identifier.citationChemistry - A European Journal 16(14): 4259-4265 (2010)-
dc.identifier.urihttp://hdl.handle.net/10261/53069-
dc.descriptionet al.-
dc.description.abstractThe cyclic decapeptide gramicidin S (GS) was used as a model for the evaluation of four turn mimetics. For this purpose, one of the D-Phe-Pro two-residue turn motifs in the rigid cyclic β-hairp0in structure of GS was replaced with morpholine amino acids (MAA 2-5), differing in stereochemistry and length of the side-chain. The conformational properties of the thus obtained GS analogues (6-9) was assessed by using NMR spectroscopy and X-ray crystallography, and correlated with their biological properties (antimicrobial and hemolytic activity). We show that compound 8, containing the dipeptide isostere trans-MAA 4, has an apparent high structural resemblance with GS and that its antibacterial activity against a panel of Gram positive and -negative bacterial strains is better than the derivatives 6, 7 and 9. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.-
dc.description.sponsorshipEste trabajo ha sido financiado por una beca del Leiden Institute of Chemistry y por la subvención BFU2008-01588/BMC del Ministerio español de Ciencia e Innovación. José M. Otero ha sido apoyado económicamente por un contratro “Angeles Alvariño” de la Xunta de Galicia.-
dc.language.isoeng-
dc.publisherWiley-VCH-
dc.rightsclosedAccess-
dc.titleGramicidin S derivatives containing cis- and trans-morpholine amino acids (MAAS) as turn mimetics-
dc.typeartículo-
dc.identifier.doi10.1002/chem.200902984-
dc.date.updated2012-07-10T10:26:21Z-
dc.description.versionPeer Reviewed-
dc.type.coarhttp://purl.org/coar/resource_type/c_6501es_ES
item.openairetypeartículo-
item.grantfulltextnone-
item.cerifentitytypePublications-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.fulltextNo Fulltext-
item.languageiso639-1en-
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