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Stereoselective synthesis of β-linked TBDMS-protected chitobiose-asparagine: a versatile building block for amyloidogenic glycopeptides

✍ Scribed by Carlos J Bosques; Vincent W.-F Tai; Barbara Imperiali

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
117 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

A simple and efficient synthesis of a Fmoc-L-Asn[b-chitobiose(TBDMS) 5 ]-OH with selectivity for the b-linked carbohydrate is described. The utility of this building block is illustrated in the synthesis of a glycosylated amyloidogenic peptide representing the 175-195 † fragment of the mouse prion protein (PrPGP).

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✍ 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%.