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

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

Author Cavalcante, Romulo S. Google Scholar
Brito, Adriana S. Google Scholar
Palhares, Lais C. G. F. Google Scholar
Lima, Marcelo A. Autor UNIFESP Google Scholar
Cavalheiro, Renan P. Autor UNIFESP Google Scholar
Nader, Helena B. Autor UNIFESP Google Scholar
Sassaki, Guilherme L. Google Scholar
Chavante, Suely F. Google Scholar
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 (delta 4.62/106.0) corresponding to unusual 2,3-di-O-Sulfo-GlcA (similar to 36%), U3(3S) (delta 4.42/84.1, similar to 63%) and U2(2S) (4.12/80.1, similar to 50%) substitutions were confirmed. In addition, non-sulfated GlcA (delta 4.5/106.3) linked to 4-O-(A1(4S), 36%) or 6-O-Sulfo (A1(6S), 28%) GalNAc (delta 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.
Keywords Chondroitin sulfate
NMR spectroscopy
Structural caracterization
Litopenaeus vannamei
xmlui.dri2xhtml.METS-1.0.item-coverage Oxford
Language English
Sponsor CNPq (Conselho Nacional de Desenvolvimento e Tecnologico) [456160/2014-0]
CAPES (Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior)
FAPESP (Fundacao de Amparo a Pesquisa do Estado de Sao Paulo), Brazil
UFPR NMR Center
CAPES
Date 2018
Published in Carbohydrate Polymers. Oxford, v. 183, p. 192-200, 2018.
ISSN 0144-8617 (Sherpa/Romeo, impact factor)
Publisher Elsevier Sci Ltd
Extent 192-200
Origin http://dx.doi.org/10.1016/j.carbpol.2017.12.018
Access rights Open access Open Access
Type Article
Web of Science ID WOS:000423715000020
URI https://repositorio.unifesp.br/handle/11600/54096

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