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Concentration Dependence of Glycosylation Outcome: A Clue to Reproducibility and Understanding the Reasons Behind

Authors

  • Leonid O. Kononov,

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
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  • Nelly N. Malysheva,

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
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  • Anna V. Orlova,

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
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  • Alexander I. Zinin,

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
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  • Tatiana V. Laptinskaya,

    1. Faculty of Physics, M. V. Lomonosov Moscow State University, Leninskie Gory, 119992 Moscow, Russian Federation
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  • Elena G. Kononova,

    1. Laboratory of Molecular Spectroscopy, A. N. Nesmeyanov Institute of Organo-Element Compounds, Vavilova 28, 119991 Moscow, Russian Federation
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  • Natalya G. Kolotyrkina

    1. N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148
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  • Dedicated to the memory of the late Professor Leon V. Backinowsky

Abstract

Changes in the concentration of reagents (0.009–0.2 M) have been shown to dramatically effect the yield and stereoselectivity of glycosylation with a sialic acid based glycosyl donor in a complex nonlinear manner that correlates with changes in the structures of the supramers of the reagents. The yield of disaccharide gradually increases with concentration and levels off at concentrations of glycosyl donor higher than 69 mM. The ratio of anomers is very high at some concentrations (α/β ≈ 20:1), moderate (α/β ≈ 8:1) or very low (α/β ≈ 4:1) at others. The formation of mixed supramers of glycosyl donor and glycosyl acceptor at concentrations exceeding 69 mM was detected by polarimetry and laser light scattering.

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