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Synthesis of mono- and di-α-l-fucosylated 2-acetamido-2-deoxy-N-glycyl-β-d-glucopyranosylamines, spacered fragments of glycans of N-glycoproteins

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Abstract

α-l-Fucp-(1→3)-d-GlcNAc, α-l-Fucp-(1→6)-[α-l-Fucp-(1→3)]-d-GlcNAc, and β-d-Galp-(1→3)-[α-l-Fucp-(1→4)]-d-GlcNAc were converted into corresponding β-glycopyranosylamines by action of ammonium carbamate in aqueous boric acid, or in aqueous methanol in case of α-l-Fucp-(1→6)-d-GlcNAc. N-Acylation of these fucooligosaccharides with N-Z-glycine N-hydroxysuccinimide ester (Z is benzyloxycarbonyl) followed by hydrogenolytic removal of Z-group afforded corresponding N-glycyl-β-glycopyranosylamines of these fucooligosaccharides; three of them model carbohydrate-peptide region of N-glycoproteins, and the forth is an amino-spacered Lea-antigen.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    L. M. Likhosherstov, O. S. Novikova, N. N. Malysheva & V. E. Piskarev

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  1. L. M. Likhosherstov
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  2. O. S. Novikova
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  3. N. N. Malysheva
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  4. V. E. Piskarev
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Correspondence to L. M. Likhosherstov.

Additional information

On the occasion of the 100th anniversary of the birth of Academician N. K. Kochetkov (1915—2005).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1134—1141, May, 2015.

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Likhosherstov, L.M., Novikova, O.S., Malysheva, N.N. et al. Synthesis of mono- and di-α-l-fucosylated 2-acetamido-2-deoxy-N-glycyl-β-d-glucopyranosylamines, spacered fragments of glycans of N-glycoproteins. Russ Chem Bull 64, 1134–1141 (2015). https://doi.org/10.1007/s11172-015-0990-7

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  • DOI: https://doi.org/10.1007/s11172-015-0990-7

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