From a marine neuropeptide to antimicrobial pseudopeptides containing aza-β(3)-amino acids: structure and activity. - Inserm - Institut national de la santé et de la recherche médicale Accéder directement au contenu
Article Dans Une Revue Journal of Medicinal Chemistry Année : 2012

From a marine neuropeptide to antimicrobial pseudopeptides containing aza-β(3)-amino acids: structure and activity.

Résumé

Incorporation of aza-β(3)-amino acids into an endogenous neuropeptide from mollusks (ALSGDAFLRF-NH(2)) with weak antimicrobial activity allows the design of new AMPs sequences. Depending on the nature of the substitution, this can render the pseudopeptides inactive or lead to a drastic enhancement of the antimicrobial activity without high cytotoxicity. Structural studies of the pseudopeptides carried out by NMR and circular dichroism show the impact of aza-β(3)-amino acids on peptide structure. The first three-dimensional structures of pseudopeptides containing aza-β(3)-amino acids in aqueous micellar SDS were determined and demonstrate that the hydrazino turn can be formed in aqueous solution. Thus, AMP activity can be modulated through structural modifications induced by the nature and the position of such amino acid analogues in the peptide sequences.
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Dates et versions

inserm-00713241 , version 1 (01-03-2013)

Identifiants

Citer

Mathieu Laurencin, Baptiste Legrand, Emilie Duval, Joël Henry, Michèle Baudy-Floc'H, et al.. From a marine neuropeptide to antimicrobial pseudopeptides containing aza-β(3)-amino acids: structure and activity.. Journal of Medicinal Chemistry, 2012, 55 (5), pp.2025-34. ⟨10.1021/jm2011595⟩. ⟨inserm-00713241⟩
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