𝔖 Bobbio Scriptorium
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Synthesis of an Asparagine-Linked Heptasaccharide − Basic Structure of N-Glycans

✍ Scribed by M. Vittoria Chiesa; Richard R. Schmidt

Book ID
102676648
Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
583 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

Galβ

)-GlcNAcβ(1-4)GlcNAcβ(1-N)Asn (1) was disconnected into building blocks 2-6. N-Dimethylmaleoyl (DMM) protected glucosamine 3 was readily obtained from glucosamine. Transformation of 3 into 4-O-unprotected glucosamine derivatives 9, 14, and 18 furnished the intermediates required for the incorporation of the three differently linked glucosamine residues. Thus, disaccharide 20 was obtained from acceptor 9 and glucosyl donor 19 and converted into protected Manβ(1-4)GlcNAc disaccharide donor 5 by inversion of the configuration at C-2 of the glucose residue. Glycosylation of acceptor 18 with known galactosyl donor 26 afforded protected lactosamine donor 6. The synthesis of asparagine building block 2 and of mannosyl donor 4 has already been reported. With building blocks 2-6 in hand, the synthesis of

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A practical and efficient synthesis of complex-type biantennary heptasaccharide-asparagine conjugate, a key building block for the synthesis of complex N-linked glycopeptides
✍ Zhong-Wu Guo; Yoshiaki Nakahara; Tomoya Ogawa 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 238 KB

The complex-type biantennary heptasaccharide-asparagine conjugate (2) of Nlinked glycoproteins was synthesized from monosaccharide units 3, 4, 6, 7 and 8 in 7 steps with an overall yield of 18.4%.