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Synthesis of polymeric neoglycoconjugates based onN-substituted polyacrylamides

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Abstract

Several types of polymeric glycoconjugates,N-substituted polyacrylamides, have been synthesized by the reaction of activated polymers with ω-aminoalkylglycosides: (i) (carbohydrate-spacer) n -polyacrylamide, ‘pseudopolysaccharides’; (ii) (carbohydrate-spacer) n -phosphatidylethanolamine m -polyacrylamide, neoglycolipids, derivatives of phosphatidylethanolamine; (iii) (carbohydrate-spacer) n -biotin m -polyacrylamide, biotinylated probes; (iv) (carbohydrate-spacer) n -polyacrylamide-(macroporous glass), affinity sorbents based on macroporous glass, covalently coated with polyacrylamide. An almost quantitative yield in the conjugation reaction makes it possible to insert in the conjugate a predetermined quantity of the ligand(s).

Pseudopolysaccharides proved to be a suitable form of antigen for activation of polystyrene and poly(vinyl chloride) plates (ELISA) and nitrocellulose membranes (dot blot), being advantageous over traditional neoglycoproteins. Polyvalent glycolipids insert well in biological membranes: their physical properties, particularly solubility, can be changed in a desired direction. Biotinylated derivatives were used as probes for detection and analysis of lectins.

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Abbreviations

sp:

spacer arm

PAA:

polyacrylamide

PE:

phosphatidylethanolamine

Biot:

biotin

MPGlass:

macroporous glass 200 Å

ELISA:

enzyme-linked immunosorbent assay

HPLC:

high-performance liquid chromatography

AIBN:

azodiisobutyronitrile

BSA:

bovine serum albumin

DMG:

3,6-di-O-methyl-d-glucose

TLC:

thin-layer chromatography

DMF:

dimethylformamide

DMSO:

dimethylsulfoxide

RI:

refractive index

PBS:

phosphate buffered saline (0.14m NaCl, 0.01m sodium phosphate, pH 7.3)

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Authors and Affiliations

  1. Shemyakin Institute of Bioorganic Chemistry, Academy of Sciences, Moscow, ul. Miklukho-Maklaya 16/10, 117871 GSP-7, V-437, Moscow, Russian Federation

    Nicolai V. Bovin, Elena Yu. Korchagina, Tatyana V. Zemlyanukhina, Nargiz E. Byramova, Oksana E. Galanina, Alexandr E. Zemlyakov, Alexandr E. Ivanov, Vitaly P. Zubov & Larisa V. Mochalova

Authors
  1. Nicolai V. Bovin
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  2. Elena Yu. Korchagina
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  3. Tatyana V. Zemlyanukhina
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  4. Nargiz E. Byramova
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  5. Oksana E. Galanina
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  6. Alexandr E. Zemlyakov
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  7. Alexandr E. Ivanov
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  8. Vitaly P. Zubov
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  9. Larisa V. Mochalova
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Bovin, N.V., Korchagina, E.Y., Zemlyanukhina, T.V. et al. Synthesis of polymeric neoglycoconjugates based onN-substituted polyacrylamides. Glycoconjugate J 10, 142–151 (1993). https://doi.org/10.1007/BF00737711

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  • DOI: https://doi.org/10.1007/BF00737711

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