| The biosynthesis of N-glycoloylneuraminic acid occurs by hydroxylation of the CMP-glycoside of N-acetylneuraminic acid. | |
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MedLine Citation:
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PMID: 3202954 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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L Shaw; R Schauer |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Biological chemistry Hoppe-Seyler Volume: 369 ISSN: 0177-3593 ISO Abbreviation: Biol. Chem. Hoppe-Seyler Publication Date: 1988 Jun |
Date Detail:
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Created Date: 1989-02-09 Completed Date: 1989-02-09 Revised Date: 2012-05-24 |
Medline Journal Info:
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Nlm Unique ID: 8503054 Medline TA: Biol Chem Hoppe Seyler Country: GERMANY, WEST |
Other Details:
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Languages: eng Pagination: 477-86 Citation Subset: IM; S |
Affiliation:
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Biochemisches Institut der Universität zu Kiel. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Carbon Radioisotopes Cytidine Monophosphate N-Acetylneuraminic Acid / metabolism* Cytochrome P-450 Enzyme System Hexosamines / metabolism Hydroxylation 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* Swine Tritium |
| Chemical | |
Reg. No./Substance:
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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 1.14.18.2/CMPacetylneuraminate monooxygenase; EC 2.4.99.-/Sialyltransferases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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