Synthesis of N-glycyl-β-glycopyranosylamines, derivatives of main human secreted oligosaccharide core structures

Abstract

β-Glycopyranosylamines were synthesized by the reaction of ammonium carbamate with di-, tetra-, and hexasaccharides, corresponding to the human milk and urine oligosaccharide core structures, in aqueous methanolic solution in the presence of NH3. The N-acylation of these β-glycopyranosylamines with N-Boc-glycine N-hydroxysuccinimide ester followed by removal of the Boc group afforded N-glycyl-β-glycopyranosylamines of the corresponding oligosaccharides in yields of up to 60%.

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Correspondence to L. M. Likhosherstov.

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Dedicated to Corresponding Member of the Russian Academy of Sciences G. I. Nikishin on the occasion of his 90th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0411–0415, February, 2019.

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Likhosherstov, L.M., Novikova, O.S., Kolotyrkina, N.G. et al. Synthesis of N-glycyl-β-glycopyranosylamines, derivatives of main human secreted oligosaccharide core structures. Russ Chem Bull 68, 411–415 (2019). https://doi.org/10.1007/s11172-019-2401-y

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Key words

  • oligosaccharides
  • human milk
  • human urine
  • β-glycopyranosylamines
  • N-acylation
  • N-glycyl-β-glycopyranosylamines