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Conjugates of cyclooligosaccharide scaffolds and carbohydrate ligands: Methods for synthesis and the interaction with lectins

Abstract

The main approaches to the preparation of mono- and oligodentate glycoconjugates based on cyclodextrin and cyclooligo-β-(1 → 6)-D-glucosamine scaffolds are surveyed in the review. The data on the biological activity of the glycoconjugates are discussed exemplified in their interaction with carbohydrate-binding proteins named lectins.

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Abbreviations

HMPTA:

hexamethyl phosphotriamide

ASF:

asialofetuin

CD:

cyclodextrin

DABCO:

1,4-diazabicyclo[2.2.2]octane

DIC:

N,N′-diisopropylcarbodiimide

DMPU:

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

DTE:

1,4-dimercaptobutan-2,3-diol

EDAC:

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

ELISA:

enzyme-linked immunosorbent assay

ELLA:

enzyme-linked lectin assay

HBTU-BF4:

O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

HIA:

hemagglutination inhibition assay

HOBT:

1-hydroxybenzotriazole

IC50:

50% inhibition concentration

ITS:

isothermal calorimetric titration

LPS:

lipopolysaccharide

MALDI:

matrix-assisted laser desorption-ionization

MS:

mass spectrometry

MSNT:

1-(2-mesitylenesulfonyl)-3-nitro-1,2-4-triazol

Py:

pyridine

Py-BOP:

(benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

SPR:

surface plasmon resonance

Sugar:

carbohydrate residue

Tf:

trifluoromethylsulfonyl

TNFα:

tumor necrosis factor α

UDPGal:

uridine diphosphate galactose

μW:

microwave irradiation. Abbreviated names and carbohydrate specificity of lectins: ConA, concanavalin A from Canavalia ensiformis, specific to mannose and glucose

EcorL:

Erythrina corallodendron lectin, specific to galactose

GSI:

Griffonia simplicifolia I lectin, specific to galactose

KbCWL:

Kluyveromyces bulgaricus lectin, specific to galactose

LcH:

Lens culinaris lectin, specific to mannose, glucose, and fucose

LecA:

Pseudomonas aeruginosa lectin, specific to galactose

PNA:

Arachis hypogea lectin, specific to galactose

PSA:

Pisum sativum lectin, specific to mannose and glucose

VAA:

Viscum album lectin, specific to galactose

WGA:

lectin of Triticum vulgaris sprouts, specific to N-acetylglucoseamine and sialic acid

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Correspondence to N. E. Nifantiev.

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Original Russian Text © D.V. Titov, M.L. Gening, Yu.E. Tsvetkov, N.E. Nifantiev, 2013, published in Bioorganicheskaya Khimiya, 2013, Vol. 39, No. 5, pp. 509–546.

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Titov, D.V., Gening, M.L., Tsvetkov, Y.E. et al. Conjugates of cyclooligosaccharide scaffolds and carbohydrate ligands: Methods for synthesis and the interaction with lectins. Russ J Bioorg Chem 39, 451–487 (2013). https://doi.org/10.1134/S1068162013050142

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  • DOI: https://doi.org/10.1134/S1068162013050142

Keywords

  • cyclodextrins
  • cyclooligo-β-(1 → 6)-D-glucosamines
  • glycoconjugates
  • lectins
  • cluster glycoside effect
  • multivalency
  • biological activity