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Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative

Galina Valentinovna Pazynina 1
Galina Valentinovna Pazynina
, 
Inna Stanislavovna Popova 1
Inna Stanislavovna Popova
, 
Ivan Mikhailovich Belyanchikov 1
Ivan Mikhailovich Belyanchikov
, 
Alexander Borisovich Tuzikov 1
Alexander Borisovich Tuzikov
, 
10.1016/j.mencom.2012.06.007
Published 2012-06-13
Communication , Volume 22, Issue 4, 194-195
3
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Pazynina G. V. et al. Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative // Mendeleev Communications. 2012. Vol. 22. No. 4. pp. 194-195.
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Pazynina G. V., Popova I. S., Belyanchikov I. M., Tuzikov A. B., Bovin N. V. Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative // Mendeleev Communications. 2012. Vol. 22. No. 4. pp. 194-195.
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TY - JOUR
DO - 10.1016/j.mencom.2012.06.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.06.007
TI - Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative
T2 - Mendeleev Communications
AU - Pazynina, Galina Valentinovna
AU - Popova, Inna Stanislavovna
AU - Belyanchikov, Ivan Mikhailovich
AU - Tuzikov, Alexander Borisovich
AU - Bovin, Nicolai Vladimirovich
PY - 2012
DA - 2012/06/13
PB - Mendeleev Communications
SP - 194-195
IS - 4
VL - 22
ER -
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@article{2012_Pazynina,
author = {Galina Valentinovna Pazynina and Inna Stanislavovna Popova and Ivan Mikhailovich Belyanchikov and Alexander Borisovich Tuzikov and Nicolai Vladimirovich Bovin},
title = {Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.06.007},
number = {4},
pages = {194--195},
doi = {10.1016/j.mencom.2012.06.007}
}
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Pazynina, Galina Valentinovna, et al. “Synthesis of trisaccharide 6’ SiaLec and its 6-O-Su derivative.” Mendeleev Communications, vol. 22, no. 4, Jun. 2012, pp. 194-195. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.06.007.

Keywords

Lewis C trisaccharide
sialylation
sulfation

Abstract

The synthetic approach to 6'SiaLec and its 6-O-Su derivative comprised α-sialylation of a protected Lec derivative, 2,3-di-OAcGalβ1-3(3-OAc-6-OBn)GlcNAcβ1-Osp (68% yield) as the key stage. Deprotection of the obtained trisaccharide (three stages, 79% overall yield) led to Neu5Acα2-6Galβ1-3GlcNAcβ1-Osp; partial deprotection followed by selective sulfation and total deprotection – to Neu5Acα2-6Galβ1-3(6-O-Su)GlcNAcβ1-Osp (four stages, 72% overall yield).

References

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Simple stereoselective synthesis of α2-6 sialooligosaccharides
Pazynina G., Tuzikov A., Chinarev A., Obukhova P., Bovin N.
Tetrahedron Letters, 2002
3.
Koenigs-Knorr Glycosylation with Neuraminic Acid Derivatives
Pazynina G., Nasonov V., Belyanchikov I., Brossmer R., Maisel M., Tuzikov A., Bovin N.
International Journal of Carbohydrate Chemistry, 2010
4.
Pazynina G.V., Severov V.V., Maisel M.L., Belyanchikov I.M., Bovin N.V.
Mendeleev Communications, 2008
5.
Chemical synthesis of 6(GlcNAc)- and 6(Gal)-O-sulfated SiaLeX tetrasaccharides in spacer-armed form
Pazynina G., Sablina M., Mayzel M., Nasonov V., Tuzikov A., Bovin N.
Glycobiology, 2009