Biosynthesis of heparin. Loss of C-5 hydrogen during conversion of d-glucuronic to l-iduronic acid residues

Ulf Lindahl; Ingvar Jacobsson; Magnus Hook; Gudrun Backstrom; David S. Feingold

doi:10.1016/0006-291X(76)91073-1

Biosynthesis of heparin. Loss of C-5 hydrogen during conversion of d-glucuronic to l-iduronic acid residues

Ulf Lindahl, Ingvar Jacobsson, Magnus Hook, Gudrun Backstrom, David S. Feingold

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Abstract

Microsomal fraction from mouse mastocytoma was incubated with UDP-N-acetylglucosamine and ³H-, ¹⁴C-labeled UDP-glucuronic acid. Enzymatic sulfation of the resulting heparin-precursor polysaccharide (by addition of 3′-phosphoadenylylsulfate) was accompanied by selective loss of ³H from C5, but not from C2 or C4, of the uronic acid residues. Analysis of the sulfated product showed C5-³H in the glucuronic acid but not in the iduronic acid component. The formation of l-iduronic acid residues by C5-epimerization of d-glucuronic acid units at the polymer level thus involves loss of hydrogen at C5.

Original language	English
Pages (from-to)	492-499
Number of pages	8
Journal	Biochemical and Biophysical Research Communications
Volume	70
Issue number	2
DOIs	https://doi.org/10.1016/0006-291X(76)91073-1
State	Published - May 17 1976

ASJC Scopus subject areas

Biochemistry
Biophysics
Molecular Biology

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title = "Biosynthesis of heparin. Loss of C-5 hydrogen during conversion of d-glucuronic to l-iduronic acid residues",

abstract = "Microsomal fraction from mouse mastocytoma was incubated with UDP-N-acetylglucosamine and 3H-, 14C-labeled UDP-glucuronic acid. Enzymatic sulfation of the resulting heparin-precursor polysaccharide (by addition of 3′-phosphoadenylylsulfate) was accompanied by selective loss of 3H from C5, but not from C2 or C4, of the uronic acid residues. Analysis of the sulfated product showed C5-3H in the glucuronic acid but not in the iduronic acid component. The formation of l-iduronic acid residues by C5-epimerization of d-glucuronic acid units at the polymer level thus involves loss of hydrogen at C5.",

author = "Ulf Lindahl and Ingvar Jacobsson and Magnus Hook and Gudrun Backstrom and Feingold, {David S.}",

note = "Funding Information: ACKNOWLEDGEMENTTh: is work was supported by Grants 13X-2309 and 13X-4486 from the Swedish Medical ReseaZ;ch Council, Grant 53 from the Swedish Cancer Society, Konung Gustav V:s 80-arsfond, the Royal Veterinary College of Sweden, and Grant AM-18160 from the National Institute of Arthritis, Metabolism, and Digestive Diseases. The present report is No. 5 in a series where the preceding paper is Reference 3. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

year = "1976",

month = may,

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doi = "10.1016/0006-291X(76)91073-1",

language = "English",

volume = "70",

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T1 - Biosynthesis of heparin. Loss of C-5 hydrogen during conversion of d-glucuronic to l-iduronic acid residues

AU - Lindahl, Ulf

AU - Jacobsson, Ingvar

AU - Hook, Magnus

AU - Backstrom, Gudrun

AU - Feingold, David S.

N1 - Funding Information: ACKNOWLEDGEMENTTh: is work was supported by Grants 13X-2309 and 13X-4486 from the Swedish Medical ReseaZ;ch Council, Grant 53 from the Swedish Cancer Society, Konung Gustav V:s 80-arsfond, the Royal Veterinary College of Sweden, and Grant AM-18160 from the National Institute of Arthritis, Metabolism, and Digestive Diseases. The present report is No. 5 in a series where the preceding paper is Reference 3. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 1976/5/17

Y1 - 1976/5/17

N2 - Microsomal fraction from mouse mastocytoma was incubated with UDP-N-acetylglucosamine and 3H-, 14C-labeled UDP-glucuronic acid. Enzymatic sulfation of the resulting heparin-precursor polysaccharide (by addition of 3′-phosphoadenylylsulfate) was accompanied by selective loss of 3H from C5, but not from C2 or C4, of the uronic acid residues. Analysis of the sulfated product showed C5-3H in the glucuronic acid but not in the iduronic acid component. The formation of l-iduronic acid residues by C5-epimerization of d-glucuronic acid units at the polymer level thus involves loss of hydrogen at C5.

AB - Microsomal fraction from mouse mastocytoma was incubated with UDP-N-acetylglucosamine and 3H-, 14C-labeled UDP-glucuronic acid. Enzymatic sulfation of the resulting heparin-precursor polysaccharide (by addition of 3′-phosphoadenylylsulfate) was accompanied by selective loss of 3H from C5, but not from C2 or C4, of the uronic acid residues. Analysis of the sulfated product showed C5-3H in the glucuronic acid but not in the iduronic acid component. The formation of l-iduronic acid residues by C5-epimerization of d-glucuronic acid units at the polymer level thus involves loss of hydrogen at C5.

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Biosynthesis of heparin. Loss of C-5 hydrogen during conversion of d-glucuronic to l-iduronic acid residues

Abstract

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