Synthesis of Spacered Disaccharides Structurally Related to the Fucosylated Chondroitin Sulfates from Sea Cucumbers Holothuria nobilis and Psolus peronii

Synthesis of Spacered Disaccharides Structurally Related to the Fucosylated Chondroitin Sulfates from Sea Cucumbers Holothuria nobilis and Psolus peronii Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1608-3393 , E-ISSN: 1070-4280

Output data

Year: 2025, Volume: 61, Number: 6, Pages: 1043-1055 Pages count : 13 DOI: 10.1134/s1070428025602304

Authors

Serpokrylov Z.V. ^1,2 , Yashunsky D.V. ² , Sukhova E.V. ² , Krylov V.B. ² , Nifantiev N.E. ²

Affiliations

1	D.I. Mendeleev University of Chemical Technology of Russia, Faculty of Pharmaceutical and Chemical Technology, 125047, Moscow, Russia
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

The synthesis of selectively 3,4′,6′-tri- and 3,4,4′,6′-tetra-O-sulfated derivatives of the aminopropyl glycoside of the disaccharide α-D-GalNAc-(1→2)-α-L-Fuc (1 and 2), structurally related to highly unusual carbohydrate chain fragments of hexosaminoglycans found in the side chains of fucosylated chondroitin sulfates (FCS) from sea cucumbers Holothuria nobilis and Psolus peronii, is described. Spacered disaccharides 1 and 2 were obtained via a common synthetic route involving selectively protected L-fucose and phenyl-1-seleno-2-azido-2-deoxygalactose building blocks, the latter synthesized by azidophenylselenylation of triacetylgalactal. Target compounds 1 and 2 will be used as model structures to identify the pharmacophoric elements within these FCS that are responsible for their biological activity.

Serpokrylov Z.V. , Yashunsky D.V. , Sukhova E.V. , Krylov V.B. , Nifantiev N.E.
Synthesis of Spacered Disaccharides Structurally Related to the Fucosylated Chondroitin Sulfates from Sea Cucumbers Holothuria nobilis and Psolus peronii
Russian Journal of Organic Chemistry. 2025. V.61. N6. P.1043-1055. DOI: 10.1134/s1070428025602304 WOS Scopus OpenAlex

≡ Web of science:	WOS:001529083700018
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