From a marine neuropeptide to antimicrobial pseudopeptides containing aza-ß(3)-amino acids: structure and activity.
J Med Chem
; 55(5): 2025-34, 2012 Mar 08.
Article
em En
| MEDLINE
| ID: mdl-22320306
ABSTRACT
Incorporation of aza-ß(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-ß(3)-amino acids on peptide structure. The first three-dimensional structures of pseudopeptides containing aza-ß(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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Oligopeptídeos
/
Compostos Aza
/
Neuropeptídeos
/
Peptídeos Catiônicos Antimicrobianos
/
Aminoácidos
/
Antibacterianos
Limite:
Animals
Idioma:
En
Revista:
J Med Chem
Assunto da revista:
QUIMICA
Ano de publicação:
2012
Tipo de documento:
Article
País de afiliação:
França