Document Detail

Conformationally restricted formyl methionyl tripeptide chemoattractants: a three-dimensional structure-activity study of analogs incorporating a C alpha,alpha-dialkylated glycine at position 2.
MedLine Citation:
PMID:  2520765     Owner:  NLM     Status:  MEDLINE    
The conformationally restricted CHO-L-Met-Xxx-L-Phe-OY (where Xxx = Aib, Ac3c, Ac5c, Ac6c, and Ac7c; Y = H, Me) tripeptides, analogs of the chemoattractant CHO-L-Met-L-Leu-L-Phe-OH, have been synthesized in solution by classical methods and fully characterized. Compounds were compared to determine the combined effect of backbone conformational preferences and side-chain bulkiness on the relation of three-dimensional structure to biological activity. Each peptide was tested for its ability to induce granule enzyme secretion from rabbit peritoneal polymorphonuclear leukocytes. In parallel, a conformational analysis on the CHO-blocked peptide and their tertbutyloxycarbonylated synthetic precursors was performed in the crystal state and in solution using X-ray diffraction, infrared absorption, and 1H nuclear magnetic resonance. The biological and conformational data are discussed in relation to the proposed model of the chemotactic peptide receptor of rabbit neutrophils.
C Toniolo; M Crisma; G Valle; G M Bonora; S Polinelli; E L Becker; R J Freer; Sudhanand; R B Rao; P Balaram
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Peptide research     Volume:  2     ISSN:  1040-5704     ISO Abbreviation:  Pept. Res.     Publication Date:    1989 Jul-Aug
Date Detail:
Created Date:  1992-06-26     Completed Date:  1992-06-26     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  8913494     Medline TA:  Pept Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  275-81     Citation Subset:  IM    
University of Padova.
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MeSH Terms
Amino Acid Sequence
Indicators and Reagents
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Sequence Data
N-Formylmethionine Leucyl-Phenylalanine / analogs & derivatives*,  chemical synthesis,  chemistry*,  pharmacology
Neutrophils / drug effects,  physiology*
Oligopeptides / chemical synthesis,  chemistry*,  pharmacology
Protein Conformation
Spectrophotometry, Infrared
Structure-Activity Relationship
Reg. No./Substance:
0/Indicators and Reagents; 0/Oligopeptides; 56-40-6/Glycine; 59880-97-6/N-Formylmethionine Leucyl-Phenylalanine

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