✦ LIBER ✦

Synthesis of a di-O-methylated pentasaccharide for use in the assay of N-acetylglucosaminyltransferase III activity

✍ Scribed by Shaheer H. Khan; Catherine A. Compston; Monica M. Palcic; Ole Hindsgaul

Publisher: Elsevier Science
Year: 1994
Tongue: English
Weight: 942 KB
Volume: 262
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(94)84185-3

No coin nor oath required. For personal study only.

✦ Synopsis

The biantennary oligosaccharide analogue beta-D-Glc pNAc-(1-->2)-alpha-D-Man p-(1-->3)-[beta-D-Glc pNAc-(1-->2)-alpha- D-Man p-(1-->6)]-beta-D-man p-O(CH2)8COOMe (3) is a potential substrate for N-acetylglucosaminyltransferases (GlcNAcTs) III-V which are present in mammalian cells. The di-O-methylated analogue of 3, beta-D-Glc pNAc-(1-->2)-[4-O-methyl-alpha-D-Man p]-(1-->3)-[beta-D-Glc pNAc-(1-->2)-[6-O-methyl-alpha-D-Man p]-(1-->6)]-beta-D-Man p-O-(CH2)8COOMe (5), was prepared by a block synthesis approach involving sequential addition of two O-methylated disaccharide donors to a protected central beta-D-Man residue. The OH groups acted on by GlcNAcT-IV and -V are protected from glycosylation in 5 since they are present as their methyl ethers. Pentasaccharide 5 was found to be an excellent substrate for GlcNAcT-III (EC 2.4.1.144) from rat kidney with Km = 0.15 mM. The product formed by incubation of 5 with a rat kidney extract, in the presence of UDP-GlcNAc, was isolated, structurally characterized by NMR spectroscopy and confirmed to be the expected di-O-methyl hexasaccharide where a beta-D-Glc pNAc residue had been added to OH-4 of the central beta-D-Man p unit.

📜 SIMILAR VOLUMES

The use of a synthetic dideoxygenated pe

The use of a synthetic dideoxygenated pentasaccharide as a specific acceptor for N-acetylglucosaminyltransferase-III

✍ Gordon Alton; Yoshimi Kanie; Ole Hindsgaul 📂 Article 📅 1993 🏛 Elsevier Science 🌐 English ⚖ 371 KB

## Mammalian glycosyltransferases assemble oligosaccharides by transferring single sugar residues from a sugar-nucleotide (the donor) to a growing carbohydrate chain (the acceptor) 1,2 The availability of an acceptor substrate is therefore a .

Synthesis of a tetrasaccharide acceptor

Synthesis of a tetrasaccharide acceptor for use in the assay of UDP-GlcpNAc:β-d-Galp-(1→4)-β-d-GlcpNAc (GlcNAc to Gal) β(1→3)-N-acetylglucosaminyltransferase activity and the pentasaccharide product that would be formed by its enzymatic glycosylation

✍ Geeta Srivastava; Ole Hindsgaul 📂 Article 📅 1992 🏛 Elsevier Science 🌐 English ⚖ 809 KB

The tetrasaccharide beta-D-Galp-(1----4)-beta-D-GlcpNAc-(1----6)-alpha-D- Manp-(1----6)-beta-D-Manp-OR (2) and the pentasaccharide beta-D-GlcpNAc-(1----3)-beta-D-Galp-(1----4)-beta-D- GlcpNAc-(1----6)-alpha-D-Manp-(1----6)-beta-D-Manp-OR (3), where R = (CH2)8COOMe, have been prepared by using combin

Combined chemical-enzymic synthesis of a

Combined chemical-enzymic synthesis of a dideoxypentasaccharide for use in a study of the specificity of N-acetyl-glucosaminyltransferase-III

✍ Kanwal J. Kaur; Ole Hindsgaul 📂 Article 📅 1992 🏛 Elsevier Science 🌐 English ⚖ 1002 KB

The biantennary oligosaccharide glycoside beta-D-GlcpNAc-(1----2)-alpha-D- Manp-(1----3)- [beta-D-GlcpNAc-(1----2)-alpha-D-Manp-(1----6)]-beta-D-Manp- OR is a potential substrate for N-acetylglucosaminyltransferases (GlcNAcTs) III-V. The dideoxypentasaccharide glycoside beta-D-GlcpNAc-(1----2)-4- de

The synthesis of 4-methylumbelliferyl α-

The synthesis of 4-methylumbelliferyl α-ketoside of N-acetylneuraminic acid and its use in a fluorometric assay for neuraminidase

✍ Robert W. Myers; Reiko T. Lee; Yuan Chuan Lee; George H. Thomas; Linda W. Reynol 📂 Article 📅 1980 🏛 Elsevier Science 🌐 English ⚖ 664 KB

The allyl group for protection in carboh

The allyl group for protection in carbohydrate chemistry. 17. Synthesis of propyl O-(3,6-di-O-methyl-β-D-glucopyranosyl)- (1→4)-O-(2,3-di-O-methyl-α-L-rhamnopyranosyl)-(1 → 2)-3-O-methyl-α-L-rhamnopyranoside: the oligosaccharide portion of the major serologically active glycolipid from Mycobacterium leprae

✍ Jill Gigg; Roy Gigg; Sheila Payne; Robert Conant 📂 Article 📅 1985 🏛 Elsevier Science 🌐 English ⚖ 474 KB

Allyl 4-O-benzyl-~-L-rhamnopyranoside was converted into allyl 4-O-benzyl-3-O-methyl-oeL-rhamnopyranoside and this was condensed with 2,3,4-tri-O-acetyl-~-L-rhamnopyranosyl chloride to give a disaccharide derivative which was converted into allyl 4 This disaccharide derivative was condensed with 2,

The Novel and Efficient Direct Synthesis

The Novel and Efficient Direct Synthesis of N,O-Acetal Compounds Using a Hypervalent Iodine(III) Reagent: An Improved Synthetic Method for a Key Intermediate of Discorhabdins.

✍ Yu Harayama; Masako Yoshida; Daigo Kamimura; Yasuyuki Kita 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 25 KB 👁 2 views