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Usp. Khim., 2021 Volume 90, Issue 2, Pages 171–198 (Mi rcr4330)

This article is cited in 7 papers

3-Amino-3-deoxy- and 4-amino-4-deoxyhexoses in the synthesis of natural carbohydrate compounds and their analogues

Yu. E. Tsvetkov, O. N. Yudina, N. E. Nifantiev

N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow

Abstract: The review considers general methods for the preparation of 3-amino-3-deoxy- and 4-amino-4-deoxyhexoses and their derivatives, including nitromethane condensation, reduction of 3- and 4-hexosulose oximes, epoxide opening with an azide ion, and nucleophilic substitution of sulfonates. The use of amino sugars of this type in the synthesis of natural carbohydrate-containing compounds and their analogues, including aminoglycoside antibiotics, glycosidase inhibitors, substrate analogues and inhibitors of glycan biosynthesis, galectin inhibitors, etc. is described.
The bibliography includes 89 references.

Keywords: 3-amino-3-deoxyhexose, 4-amino-4-deoxyhexose, aminoglycoside antibiotics, glycosidase inhibitors, galectin inhibitors, enzyme-substrate analogues, synthesis.

Received: 27.06.2020

DOI: 10.1070/RCR4974


 English version:
Russian Chemical Reviews, 2021, 90:2, 171–198

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© Steklov Math. Inst. of RAS, 2024