Document Detail

Effect of specific trinitrophenylation of the lysine epsilon amino group of glucagon on receptor binding and adenylate cyclase activation.
MedLine Citation:
PMID:  6311099     Owner:  NLM     Status:  MEDLINE    
The trinitrophenyl group was specifically introduced into the epsilon-amino group of glucagon by reaction of N alpha-citraconyl glucagon with trinitrobenzenesulfonic acid. The N alpha-citraconyl blocking group was subsequently removed by acid treatment yielding N epsilon-trinitrophenyl glucagon which was purified by anion-exchange chromatography. The derivative showed less secondary structure as measured by circular dichroism than the native hormone at pH 8.0 and at pH 2.0 in the presence of sodium dodecyl sulfate. The analog possessed 4-5% the potency of glucagon in stimulating adenylate cyclase with 90% maximal stimulation and possessed 30% the potency of glucagon in competing for glucagon-specific receptor sites in hepatic plasma membranes. Although the structure of N epsilon-trinitrophenyl glucagon is very similar to N epsilon-4-azido-2-nitrophenyl glucagon, the photoaffinity antagonist synthesized by M.D. Bregman and D. Levy [(1977) Biochem. Biophys. Res. Commun. 78, 584-590.], the biological activities of the two are different. Possible explanations for these differences are discussed.
J J Liepnieks; R M Epand
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Publication Detail:
Type:  In Vitro; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Archives of biochemistry and biophysics     Volume:  225     ISSN:  0003-9861     ISO Abbreviation:  Arch. Biochem. Biophys.     Publication Date:  1983 Aug 
Date Detail:
Created Date:  1983-10-08     Completed Date:  1983-10-08     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0372430     Medline TA:  Arch Biochem Biophys     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  102-9     Citation Subset:  IM    
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MeSH Terms
Adenylate Cyclase / metabolism*
Binding, Competitive
Cell Membrane / metabolism
Circular Dichroism
Enzyme Activation / drug effects
Glucagon / analogs & derivatives*,  chemical synthesis,  metabolism*,  pharmacology
Liver / enzymology,  metabolism*
Lysine / metabolism
Rats, Inbred Strains
Receptors, Cell Surface / metabolism*
Receptors, Glucagon
Structure-Activity Relationship
Reg. No./Substance:
0/Receptors, Cell Surface; 0/Receptors, Glucagon; 56-87-1/Lysine; 75285-60-8/N-trinitrophenylglucagon; 9007-92-5/Glucagon; EC Cyclase

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

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