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    
Abstract/OtherAbstract:
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.
Authors:
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    
Affiliation:
University of Padova.
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MeSH Terms
Descriptor/Qualifier:
Alkylation
Amino Acid Sequence
Animals
Glycine
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
Rabbits
Spectrophotometry, Infrared
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Indicators and Reagents; 0/Oligopeptides; 56-40-6/Glycine; 59880-97-6/N-Formylmethionine Leucyl-Phenylalanine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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