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D-Amino Acid-Containing Lipopeptides Derived from the Lead Peptide BP100 with Activity against Plant Pathogens.
Oliveras, Àngel; Moll, Luís; Riesco-Llach, Gerard; Tolosa-Canudas, Arnau; Gil-Caballero, Sergio; Badosa, Esther; Bonaterra, Anna; Montesinos, Emilio; Planas, Marta; Feliu, Lidia.
Afiliação
  • Oliveras À; LIPPSO, Department of Chemistry, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Moll L; Laboratory of Plant Pathology, Institute of Food and Agricultural Technology-CIDSAV-XaRTA, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Riesco-Llach G; LIPPSO, Department of Chemistry, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Tolosa-Canudas A; LIPPSO, Department of Chemistry, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Gil-Caballero S; Serveis Tècnics de Recerca (NMR), Universitat de Girona, Parc Científic i Tecnològic de la UdG, Pic de Peguera 15, 17004 Girona, Spain.
  • Badosa E; Laboratory of Plant Pathology, Institute of Food and Agricultural Technology-CIDSAV-XaRTA, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Bonaterra A; Laboratory of Plant Pathology, Institute of Food and Agricultural Technology-CIDSAV-XaRTA, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Montesinos E; Laboratory of Plant Pathology, Institute of Food and Agricultural Technology-CIDSAV-XaRTA, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Planas M; LIPPSO, Department of Chemistry, Campus Montilivi, University of Girona, 17004 Girona, Spain.
  • Feliu L; LIPPSO, Department of Chemistry, Campus Montilivi, University of Girona, 17004 Girona, Spain.
Int J Mol Sci ; 22(12)2021 Jun 21.
Article em En | MEDLINE | ID: mdl-34205705
From a previous collection of lipopeptides derived from BP100, we selected 18 sequences in order to improve their biological profile. In particular, analogues containing a D-amino acid at position 4 were designed, prepared, and tested against plant pathogenic bacteria and fungi. The biological activity of these sequences was compared with that of the corresponding parent lipopeptides with all L-amino acids. In addition, the influence of the length of the hydrophobic chain on the biological activity was evaluated. Interestingly, the incorporation of a D-amino acid into lipopeptides bearing a butanoyl or a hexanoyl chain led to less hemolytic sequences and, in general, that were as active or more active than the corresponding all L-lipopeptides. The best lipopeptides were BP475 and BP485, both incorporating a D-Phe at position 4 and a butanoyl group, with MIC values between 0.8 and 6.2 µM, low hemolysis (0 and 24% at 250 µM, respectively), and low phytotoxicity. Characterization by NMR of the secondary structure of BP475 revealed that the D-Phe at position 4 disrupts the α-helix and that residues 6 to 10 are able to fold in an α-helix. This secondary structure would be responsible for the high antimicrobial activity and low hemolysis of this lipopeptide.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Oligopeptídeos / Doenças das Plantas / Testes de Sensibilidade Microbiana / Lipopeptídeos / Anti-Infecciosos Tipo de estudo: Evaluation_studies Idioma: En Revista: Int J Mol Sci Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Espanha

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Oligopeptídeos / Doenças das Plantas / Testes de Sensibilidade Microbiana / Lipopeptídeos / Anti-Infecciosos Tipo de estudo: Evaluation_studies Idioma: En Revista: Int J Mol Sci Ano de publicação: 2021 Tipo de documento: Article País de afiliação: Espanha