Synthesis, biological activity, conformational analysis by NMR and molecular modeling of N-formyl-L-Met-L-Pro-L-Phe-OMe, a proline analogue of the chemotactic peptide N-formyl-L-Met-L-Leu-L-Phe-OH.
Int J Pept Protein Res
; 41(6): 595-605, 1993 Jun.
Article
in En
| MEDLINE
| ID: mdl-8394292
ABSTRACT
The tripeptide N-formyl-Met-Pro-Phe-OMe (f-MPF-OMe), an analogue of the signal peptide N-formyl-Met-Leu-Phe-OH (f-MLF-OH), was synthesized and its chemotactic activity evaluated; it showed no activity in either superoxide production or calcium mobility with human neutrophils. However, the corresponding acid f-MPF-OH retained about 25% activity in the production of superoxide. The conformation of the f-MPF-OMe analogue was evaluated by NMR spectroscopy and molecular simulation and shown to predominate in a gamma-turn with a hydrogen bond between Met CO and Phe NH. Since this analogue is not chemotactic, it is suggested that for recognition the receptor prefers a peptide with a flexible backbone, favoring an extended conformation in the binding site.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Chemotactic Factors
/
Chemotaxis, Leukocyte
/
N-Formylmethionine Leucyl-Phenylalanine
/
Neutrophils
Type of study:
Prognostic_studies
Limits:
Humans
Language:
En
Journal:
Int J Pept Protein Res
Year:
1993
Document type:
Article
Affiliation country:
Canada