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Closed Access item Gramicidin S derivatives containing cis- and trans-morpholine amino acids (MAAS) as turn mimetics

Authors:Raaij, Mark J. van
Overhand, Mark
Issue Date:2010
Publisher:Wiley-VCH
Citation:Chemistry - A European Journal 16(14): 4259-4265 (2010)
Abstract:The 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.
Description:et al.
URI:http://hdl.handle.net/10261/53069
Identifiers:doi: 10.1002/chem.200902984
issn: 0947-6539
Appears in Collections:(IBMB) Artículos

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