Document Detail

Sequence-dependent reactivity of model peptides with glyceraldehyde.
MedLine Citation:
PMID:  2776139     Owner:  NLM     Status:  MEDLINE    
Glyceraldehyde reacted faster with tripeptides than with dipeptides. The pH profiles of the reactions with tripeptides displayed optima in the range of 8.5-10.0, approximately 1-2 pH units higher than found with dipeptides. The second amino acid residue influences not only the rate of reaction but also the extent of formation of the product of the Amadori rearrangement, the ketoamine. The presence of histidine as the second amino acid residue of either di- or tri-peptides greatly accelerated the rate of reaction perhaps by facilitating the rearrangement. Conventional amino acid analysis and liquid chromatography procedures have been used to detect intermediates and the ketoamine product. 1H-N.m.r. analysis of the reduced adducts was consistent with the assigned structures.
N Mori; Y Bai; H Ueno; J M Manning
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Carbohydrate research     Volume:  189     ISSN:  0008-6215     ISO Abbreviation:  Carbohydr. Res.     Publication Date:  1989 Jun 
Date Detail:
Created Date:  1989-10-24     Completed Date:  1989-10-24     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0043535     Medline TA:  Carbohydr Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  49-63     Citation Subset:  IM    
Rockefeller University, New York, New York 10021.
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MeSH Terms
Amino Acid Sequence
Amino Acids / analysis
Chemical Phenomena
Chromatography, Liquid
Dipeptides / analysis
Hydrogen-Ion Concentration
Magnetic Resonance Spectroscopy
Oligopeptides* / analysis
Structure-Activity Relationship
Grant Support
Reg. No./Substance:
0/Amino Acids; 0/Dipeptides; 0/Oligopeptides; 3253-17-6/alanylhistidine; 367-47-5/Glyceraldehyde; 53843-93-9/glycyl-seryl-alanine

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

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