A new method for the synthesis of aldehyde-spacered oligosaccharides by oxidation of l-tartaric acid derivative View Full Text


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Article Info

DATE

2018-02

AUTHORS

L. M. Likhosherstov, O. S. Novikova, N. G. Kolotyrkina, B. B. Berezin, V. E. Piskarev

ABSTRACT

N-(N-[(2R,3R)-2,3-Dihydroxy-3-carboxypropionyl]glycyl)-β-d-glycopyranosylamines and N-[N-(formylcarbonyl)glycyl]-β-d-glycopyranosylamines, derivatives of lactose, human milk tri-, tetra-, and pentasaccharides, and synthetic di- and trisaccharides, were synthe- sized. N-Glycyl-β-d-glycopyranosylamines of these oligosaccharides were N-acylated with (+)-di-O-acetyl-l-tartaric anhydride, and the derivatives with α-glycol and terminal carboxy groups in the aglycon moiety were obtained after O-deacylation (70—80% yield). The short-term (80 s) selective oxidation of the α-glycol group of the tartaric acid residue in these derivatives with dilute periodic acid gave the target compounds with the terminal aldehyde group in aglycon in ~90% yield. More... »

PAGES

371-376

References to SciGraph publications

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  • 2012-09. Synthesis of N-glycyl-β-glycopyranosylamines, human milk fucooligosaccharide derivatives in RUSSIAN CHEMICAL BULLETIN
  • 2015-05. Synthesis of mono- and di-α-l-fucosylated 2-acetamido-2-deoxy-N-glycyl-β-d-glucopyranosylamines, spacered fragments of glycans of N-glycoproteins in RUSSIAN CHEMICAL BULLETIN
  • 1991-04. Expedient syntheses of neoglycoproteins using phase transfer catalysis and reductive amination as key reactions in GLYCOCONJUGATE JOURNAL
  • 2008-03. Synthesis of bi- and tervalent ligands of galectins, derivatives of β-lactosylamine, with the amino group in the terminal position of the spacer in RUSSIAN CHEMICAL BULLETIN
  • 2000-08. N-glycyl-β-glycopyranosylamines, derivatives of mono- and disaccharides, and their use for the preparation of carboxylic acid glycoconjugates in RUSSIAN CHEMICAL BULLETIN
  • 2000-07. A novel approach to functionalization of allyl aglycon. Effective synthesis of selectively protected 2-aminoethyl lactoside, a common building block for the synthesis of carbohydrate chains of glycolipids in RUSSIAN CHEMICAL BULLETIN
  • 2014-02. Synthesis of N-glycyl-β-glycopyranosyl amines, derivatives of natural oligosaccharides — glucose analogs of Lex antigen in RUSSIAN CHEMICAL BULLETIN
  • 2015-06. Synthesis of mono- and di-α-l-fucosylated 2-acetamido-2-deoxy-N-glycyl-β-d-glucopyranosylamines modeling N-glycoprotein carbohydrate-peptide bond region based on 2-acetamido-N-(N-tert-butyloxycarbonylglycyl)-2-deoxy-β-d-glucopyranosylamine in RUSSIAN CHEMICAL BULLETIN
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    http://scigraph.springernature.com/pub.10.1007/s11172-018-2083-x

    DOI

    http://dx.doi.org/10.1007/s11172-018-2083-x

    DIMENSIONS

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