Document Detail

Enzymatic transfer of sialic acids modified at C-5 employing four different sialyltransferases.
MedLine Citation:
PMID:  8748149     Owner:  NLM     Status:  MEDLINE    
We present kinetic studies on the enzymatic transfer of several synthetic sialic acid analogues, modified at C-5, to distinct glycoprotein glycans by sialyltransferases differing in acceptor- and linkage-specificity. Biochemical properties of sialic acids were modified by introducing formyl-, trifluoroacetyl-, benzyloxy-carbonyl-, and aminoacetyl-groups to the amino group at C-5 of neuraminic acid. The latter substitution renders the corresponding alpha-glycoside resistant towards sialidases. The respective CMP-sialic acid analogues were prepared by CMP-sialic acid synthase with a yield of 13-55%. The kinetic parameters of several sialyltransferases for the 5-substituted CMP-glycosides differed significantly. Relative to parent CMP-NeuAc, reaction rates of human- and rat liver Gal beta 1, 4GlcNAc alpha 2,6-sialyltransferases ranged from 50 to 170%, of GalNAc alpha 2,6-sialyltransferases from 40-140%, and of Gal beta 1,3Gal-NAc alpha 2,3-sialyltransferase from 20-50%. Resialylation of asialo-alpha 1-acid glycoprotein by 5-N-formyl- and 5-N-aminoacetyl-neuraminic acid employing rat liver Gal beta 1,4GlcNAc alpha 2,6-sialyltransferase proceeded to about 80% of galactose sites which is identical to the extent achieved with parent NeuAc. According to our data, neosialoglycoconjugates which carry sialic acids modified at the N-acetyl group can be prepared for structure-function analysis, as this position seems crucial for recognition of adhesion proteins and influenza viruses.
H J Gross; R Brossmer
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  Glycoconjugate journal     Volume:  12     ISSN:  0282-0080     ISO Abbreviation:  Glycoconj. J.     Publication Date:  1995 Dec 
Date Detail:
Created Date:  1996-11-15     Completed Date:  1996-11-15     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8603310     Medline TA:  Glycoconj J     Country:  ENGLAND    
Other Details:
Languages:  eng     Pagination:  739-46     Citation Subset:  IM    
Institut für Biochemie II, Heidelberg, Germany.
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MeSH Terms
Carbohydrate Conformation
Carbohydrate Sequence
Molecular Sequence Data
Polysaccharides / chemistry*
Sialic Acids / chemistry*
Sialyltransferases / chemistry*
Substrate Specificity
Reg. No./Substance:
0/Polysaccharides; 0/Sialic Acids; EC 2.4.99.-/Sialyltransferases

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

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