Document Detail

The biosynthesis of N-glycoloylneuraminic acid occurs by hydroxylation of the CMP-glycoside of N-acetylneuraminic acid.
MedLine Citation:
PMID:  3202954     Owner:  NLM     Status:  MEDLINE    
The biosynthesis of N-glycoloylneuraminic acid in fractionated porcine submandibular glands was investigated. The following substrates: [3H]N-acetylmannosamine, free [14C]N-acetylneuraminic acid, CMP-[14C]N-acetylneuraminic acid, [14C]N-acetylneuraminic acid linked alpha(2----3) to galactose residues, or alpha(2----6) to Gal-beta(1----4)-GlcNAc residues of porcine submandibular mucin and [14C]N-acetylneuraminic acid linked alpha(2----6) to GalNAc residues of ovine submandibular gland mucin were incubated, in the presence of cofactors, with the soluble protein, heavy membrane and microsomal fractions of porcine submandibular glands. Radio thin-layer chromatographic analysis revealed that only one substrate, CMP-[14C]N-acetylneuraminic acid, was hydroxylated. The product was identified as CMP-[14C]N-glycoloylneuraminic acid by (i) co-chromatography with non-radioactive CMP-N-glycoloylneuraminic acid standard, (ii) acid hydrolysis to free [14C]N-glycoloylneuraminic acid, (iii) alkaline hydrolysis to yield N-glycoloylneuraminic acid and 2-deoxy-2,3-didehydro-N-glycoloylneuraminic acid and (iv) transfer of [14C]N-glycoloylneuraminic acid to asialo-fetuin by sialyltransferase. 85% of CMP-N-acetylneuraminic acid hydroxylase activity was present in the soluble protein fraction, with small amounts of activity in the two particulate fractions. The CMP-N-acetylneuraminic acid hydroxylase in the soluble protein fraction had an absolute requirement for Fe2+ ions and a reducing cofactor. NADPH and NADH were by far the most effective cofactors, smaller amounts of hydroxylation could, however, be supported by ascorbic acid and 6,7-dimethyl-5,6,7,8-tetrahydrobiopterin.
L Shaw; R Schauer
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Biological chemistry Hoppe-Seyler     Volume:  369     ISSN:  0177-3593     ISO Abbreviation:  Biol. Chem. Hoppe-Seyler     Publication Date:  1988 Jun 
Date Detail:
Created Date:  1989-02-09     Completed Date:  1989-02-09     Revised Date:  2012-05-24    
Medline Journal Info:
Nlm Unique ID:  8503054     Medline TA:  Biol Chem Hoppe Seyler     Country:  GERMANY, WEST    
Other Details:
Languages:  eng     Pagination:  477-86     Citation Subset:  IM; S    
Biochemisches Institut der Universität zu Kiel.
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MeSH Terms
Carbon Radioisotopes
Cytidine Monophosphate N-Acetylneuraminic Acid / metabolism*
Cytochrome P-450 Enzyme System
Hexosamines / metabolism
Mixed Function Oxygenases / metabolism*
Mucins / metabolism
N-Acetylneuraminic Acid
Neuraminic Acids / biosynthesis*
Sialic Acids / metabolism*
Sialyltransferases / metabolism
Steroid Hydroxylases
Subcellular Fractions / enzymology
Submandibular Gland / enzymology*
Reg. No./Substance:
0/Carbon Radioisotopes; 0/Hexosamines; 0/Mucins; 0/Neuraminic Acids; 0/Sialic Acids; 10028-17-8/Tritium; 1113-83-3/N-glycolylneuraminic acid; 131-48-6/N-Acetylneuraminic Acid; 3063-71-6/Cytidine Monophosphate N-Acetylneuraminic Acid; 4773-29-9/N-acetylmannosamine; 9035-51-2/Cytochrome P-450 Enzyme System; EC 1.-/Mixed Function Oxygenases; EC 1.14.-/Steroid Hydroxylases; EC monooxygenase; EC 2.4.99.-/Sialyltransferases

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