Document Detail

Synthesis and reactivity of the monosaccharide esters of amino acids as models of teichoic acid fragment.
MedLine Citation:
PMID:  11261836     Owner:  NLM     Status:  MEDLINE    
The increasing prevalence of sepsis from gram-positive bacterial pathogens necessitates further evaluation of the basic assumptions about the molecular pathogenesis of septic shock. Since diverse physiological functions of gram-positive bacteria are controlled by the degree of esterification of teichoic acids with D-alanine, we examined the reactivity of monosaccharide esters in which anomerically free or protected D-glucose is linked through its C-6 hydroxy group to either phenylalanyl or tyrosyl residues as models for teichoic acid fragment. We show that the attached sugar moiety induces activation of the amino acid residue. Due to the enhanced reactivity of the NH2 group in the monosaccharide esters studied, the formation of products generated by intramolecular and intermolecular glycation reactions is accelerated resulting in heterogeneous mixture of compounds. These findings suggest that, if similar adducts are formed by glycation of D-alanine in teichoic acid of gram-positive bacteria, they should be examined as potential bioactive ligands or chemical message for infection.
I Jerić; L Simicić; M Stipetić; S Horvat
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Glycoconjugate journal     Volume:  17     ISSN:  0282-0080     ISO Abbreviation:  Glycoconj. J.     Publication Date:  2000 May 
Date Detail:
Created Date:  2001-03-22     Completed Date:  2001-08-16     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8603310     Medline TA:  Glycoconj J     Country:  United States    
Other Details:
Languages:  eng     Pagination:  273-82     Citation Subset:  IM    
Department of Organic Chemistry and Biochemistry, Ruder Bosković Institute, Zagreb, Croatia.
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MeSH Terms
Amino Acids / chemical synthesis*
Chromatography, High Pressure Liquid
Esters / chemical synthesis
Glucose / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Monosaccharides / chemical synthesis*,  chemistry
Teichoic Acids / chemistry*
Reg. No./Substance:
0/Amino Acids; 0/Esters; 0/Monosaccharides; 0/Teichoic Acids; 50-99-7/Glucose

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