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

Rômulo S Cavalcante; Adriana S Brito; Lais C G F Palhares; Marcelo A Lima; Renan P Cavalheiro; Helena B Nader; Guilherme L Sassaki; Suely F Chavante

doi:10.1016/j.carbpol.2017.12.018

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

Carbohydr Polym. 2018 Mar 1:183:192-200. doi: 10.1016/j.carbpol.2017.12.018. Epub 2017 Dec 13.

Authors

Rômulo S Cavalcante¹, Adriana S Brito², Lais C G F Palhares³, Marcelo A Lima⁴, Renan P Cavalheiro⁵, Helena B Nader⁵, Guilherme L Sassaki⁶, Suely F Chavante⁷

Affiliations

¹ Programa de Pós-graduação em Bioquímica e Biologia Molecular, Departamento de Bioquímica, Universidade Federal do Rio Grande do Norte, Natal, RN, Brazil; Programa de Pós-graduação em Ciências da Saúde, Departamento de Morfologia, Universidade Federal do Rio Grande do Norte, Natal, RN, Brazil.
² Programa de Pós-graduação em Bioquímica e Biologia Molecular, Departamento de Bioquímica, Universidade Federal do Rio Grande do Norte, Natal, RN, Brazil; Faculdade de Ciências da Saúde do Trairi, Universidade Federal do Rio Grande do Norte, Santa Cruz, RN, Brazil.
³ Programa de Pós-graduação em Bioquímica e Biologia Molecular, Departamento de Bioquímica, Universidade Federal do Rio Grande do Norte, Natal, RN, Brazil.
⁴ Departamento de Bioquímica, Universidade Federal de São Paulo, SP, Brazil; Department of Biochemistry, University of Liverpool, Liverpool, L69 7ZB, United Kingdom.
⁵ Departamento de Bioquímica, Universidade Federal de São Paulo, SP, Brazil.
⁶ Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Curitiba, PR, Brazil. Electronic address: guilherme.sassaki@gmail.com.
⁷ Programa de Pós-graduação em Bioquímica e Biologia Molecular, Departamento de Bioquímica, Universidade Federal do Rio Grande do Norte, Natal, RN, Brazil. Electronic address: chavantesu@hotmail.com.

PMID: 29352874
DOI: 10.1016/j.carbpol.2017.12.018

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 (δ 4.62/106.0) corresponding to unusual 2,3-di-O-Sulfo-GlcA (∼36%), U3_3S (δ 4.42/84.1, ∼63%) and U2_2S (4.12/80.1, ∼50%) substitutions were confirmed. In addition, non-sulfated GlcA (δ 4.5/106.3) linked to 4-O- (A1_4S, 36%) or 6-O-Sulfo (A1_6S, 28%) GalNAc (δ 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; Litopenaeus vannamei; NMR spectroscopy; Structural caracterization.

MeSH terms

Animals
Anticoagulants / chemistry*
Anticoagulants / pharmacology
Cells, Cultured
Chondroitin Sulfates / chemistry*
Chondroitin Sulfates / pharmacology
Decapoda / chemistry*
Glucuronic Acid / chemistry*
Hemostasis / drug effects
Male
Rabbits
Rats
Rats, Wistar

Substances

Anticoagulants
Glucuronic Acid
Chondroitin Sulfates