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2, 3-Di-O-sulfo glucuronic acid: an unmodified and unusual residue in a highly sulfated chondroitin sulfate from Litopenaeus vannamei

Cavalcante, RS; Brito, AS; Palhares, LCGF; Andrade De Lima, M; Cavalheiro, RP; Nader, HB; Sassaki, GL; Chavante, SF

2, 3-Di-O-sulfo glucuronic acid: an unmodified and unusual residue in a highly sulfated chondroitin sulfate from Litopenaeus vannamei Thumbnail


Authors

RS Cavalcante

AS Brito

LCGF Palhares

RP Cavalheiro

HB Nader

GL Sassaki

SF Chavante



Abstract

The occurrence of a natural and unmodified highly sulfated chondroitin sulfate from Litopenaeus vannamei heads (sCS) is herein reported. Its partial digestion by Chondroitinases AC and ABC together with its electrophoretic migration profile revealed it as a highly sulfated chondroitin sulfate despite its average molecular weight being similar to CSA. Using orthogonal 1D/2D NMR experiments, the anomeric signals (d 4.62/106.0) corresponding to unusual 2,3-di-O-Sulfo-GlcA (~36%), U33S (d 4.42/84.1, ~63%) and U22S (4.12/80.1, ~50%) substitutions were confirmed. In addition, non-sulfated GlcA (d 4.5/106.3) linked to 4-O- (A14S, 36%) or 6-O-Sulfo (A16S, 28%) GalNAc (d 4.64/103.5) was observed. Although the biological role of sCS in shrimp is unknown, its influence on hemostasis was also demonstrated. The sCS identification brings to light new questions about the hierarchical model of GAGs biosynthesis and contributes to the better understanding of the subtle relationship between GAGs structure and function.

Journal Article Type Article
Acceptance Date Dec 9, 2017
Publication Date Mar 1, 2018
Publicly Available Date Mar 28, 2024
Journal Carbohydrate polymers
Print ISSN 0144-8617
Publisher Elsevier
Volume 183
Pages 192--200
DOI https://doi.org/10.1016/j.carbpol.2017.12.018
Keywords Chondroitin sulfate, NMR spectroscopy, Structural caracterization, Litopenaeus vannamei
Publisher URL https://www.sciencedirect.com/science/article/pii/S0144861717314236?via\%3Dihub

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