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

Yury Evgen'evich Tsvetkov 1
Yury Evgen'evich Tsvetkov
, 
Ol'ga Nikolaevna Yudina 1
Ol'ga Nikolaevna Yudina
, 
Nikolay Eduardovich Nifantiev 1
Nikolay Eduardovich Nifantiev
1 N.D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
10.1070/RCR4974
Published 30 November 2020
Review , RCR4974, Volume 90, Issue 2, 171-198
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Tsvetkov Y. E., Yudina O. N., Nifantiev N. E. 3-Amino-3-deoxy- and 4-amino-4-deoxyhexoses in the synthesis of natural carbohydrate compounds and their analogues // Russian Chemical Reviews. 2020. Vol. 90. No. 2. pp. 171-198.
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Tsvetkov Y. E., Yudina O. N., Nifantiev N. E. 3-Amino-3-deoxy- and 4-amino-4-deoxyhexoses in the synthesis of natural carbohydrate compounds and their analogues // Russian Chemical Reviews. 2020. Vol. 90. No. 2. pp. 171-198.
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TY - JOUR
DO - 10.1070/RCR4974
UR - https://rcr.colab.ws/publications/10.1070/RCR4974
TI - 3-Amino-3-deoxy- and 4-amino-4-deoxyhexoses in the synthesis of natural carbohydrate compounds and their analogues
T2 - Russian Chemical Reviews
AU - Tsvetkov, Yury Evgen'evich
AU - Yudina, Ol'ga Nikolaevna
AU - Nifantiev, Nikolay Eduardovich
PY - 2020
DA - 2020/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 171-198
IS - 2
VL - 90
ER -
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@article{2020_Tsvetkov,
author = {Yury Evgen'evich Tsvetkov and Ol'ga Nikolaevna Yudina and Nikolay Eduardovich Nifantiev},
title = {3-Amino-3-deoxy- and 4-amino-4-deoxyhexoses in the synthesis of natural carbohydrate compounds and their analogues},
journal = {Russian Chemical Reviews},
year = {2020},
volume = {90},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4974},
number = {2},
pages = {171--198},
doi = {10.1070/RCR4974}
}
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Tsvetkov, Yury Evgen'evich, et al. “3-Amino-3-deoxy- and 4-amino-4-deoxyhexoses in the synthesis of natural carbohydrate compounds and their analogues.” Russian Chemical Reviews, vol. 90, no. 2, Nov. 2020, pp. 171-198. https://rcr.colab.ws/publications/10.1070/RCR4974.
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Keywords

3-amino-3-deoxyhexose
4-amino-4-deoxyhexose
aminoglycoside antibiotics
enzyme-substrate analogues
galectin inhibitors
glycosidase inhibitors
synthesis

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, \emph{etc}. is described.

The bibliography includes 89 references.

Funders

Russian Science Foundation
19-43-02023

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