The synthesis of hyaluronic acid related oligosaccharides and elucidation of their antiangiogenic activity

The synthesis of hyaluronic acid related oligosaccharides and elucidation of their antiangiogenic activity Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2022, Volume: 522, Article number : 108701, Pages count : DOI: 10.1016/j.carres.2022.108701

Authors

Grinkova Anna A. ¹ , Sukhova Elena V. ¹ , Ustyuzhanina Nadezhda E. ¹ , Nifantiev Nikolay E. ¹

Affiliations

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

Hyaluronic acid related di-, tri-, tetra- and hexasaccharide were synthesized as spacer-armed derivatives. 4,6-O-(p-Methoxybenzylidene-2,3-di-O-benzoyl-glucosyl sulfoxide was used as a donor for the formation of β-D-Glc-(1 → 3)-β-D-GlcNTCA interunit bond. Selective removal of p-methoxy-benzylidene protecting group, C(6) oxidation by TEMPO-BAIB system followed by methylation led to transformation of Glc unit into GlcA one. Trichloromethyloxazoline donors were used for the formation of β-D-GlcNTCA-(1 → 4)-β-D-GlcA linkages. Block-wise [1 + 2], [2 + 2], and [2 + 4] chain assembly afforded to corresponding tri-, tetra-, and hexasaccharide derivatives, respectively. The target compounds were studied as inhibitors of angiogenesis in vitro using endothelial cells and Matrigel as a medium to show the activity of tetra- and hexasaccharide but not for di- and trisaccharide.

Grinkova A.A. , Sukhova E.V. , Ustyuzhanina N.E. , Nifantiev N.E.
The synthesis of hyaluronic acid related oligosaccharides and elucidation of their antiangiogenic activity
Carbohydrate Research. 2022. V.522. 108701 . DOI: 10.1016/j.carres.2022.108701 WOS Scopus OpenAlex

≡ Web of science:	WOS:000872390300002
≡ Scopus:	2-s2.0-85139730325
≡ OpenAlex:	W4302286430