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Título: | Sequence inversion and phenylalanine surrogates at the β-Turn enhance the antibiotic activity of gramicidin S |
Autor: | Solans, Conxita CSIC ORCID ; García de la Torre, Beatriz CSIC ORCID; Fernández-Reyes, María CSIC ORCID; Santiveri, Clara M. CSIC ORCID; Jiménez, Ana I. CSIC ORCID; Andreu, David; Cativiela, Carlos CSIC ORCID | Fecha de publicación: | 2010 | Editor: | American Chemical Society | Citación: | Journal of Medicinal Chemistry 53(10): 4119- 4129 (2010) | Resumen: | A series of gramicidin S (GS) analogues have been synthesized where the Phe (i + 1) and Pro (i + 2) residues of the β-turn have been swapped while the respective chiralities (d-, l-) at each position are preserved, and Phe is replaced by surrogates with aromatic side chains of diverse size, orientation, and flexibility. Although most analogues preserve the β-sheet structure, as assessed by NMR, their antibiotic activities turn out to be highly dependent on the bulkiness and spatial arrangement of the aromatic side chain. Significant increases in microbicidal potency against both Gram-positive and Gram-negative pathogens are observed for several analogues, resulting in improved therapeutic profiles. Data indicate that seemingly minor replacements at the GS β-turn can have significant impact on antibiotic activity, highlighting this region as a hot spot for modulating GS plasticity and activity. © 2010 American Chemical Society. | URI: | http://hdl.handle.net/10261/54027 | DOI: | 10.1021/jm100143f | Identificadores: | doi: 10.1021/jm100143f issn: 0022-2623 e-issn: 1520-4804 |
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