Mar. Drugs 2012, 10(8), 1647-1661; doi:10.3390/md10081647
Article

Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber

1,2,3,†email, 1,†email, 2,3email, 1email, 1email and 1,* email
Received: 21 May 2012; in revised form: 3 July 2012 / Accepted: 24 July 2012 / Published: 10 August 2012
(This article belongs to the Special Issue Marine Glycoconjugates)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Fucosylated chondroitin sulfate (FuCS), a kind of complex glycosaminoglycan from sea cucumber, has potent anticoagulant activity. In order to understand the relationship between structures and activity, the depolymerized FuCS (dFuCS) was chosen to prepare its derivates by selective substitution at OH groups. Its O-acylation was carried out in a homogeneous way using carboxylic acid anhydrides. The structures of O-acylated derivatives were characterized by NMR. The results indicated that the 4-O-sulfated fucose residues may be easier to be acylated than the other ones in the sulfated fucose branches. But the O-acylation was always accompanied by the β-elimination, and the degree of elimination was higher as that of acylation was higher. The results of clotting assay indicated that the effect of partial O-acylation of the dFuCS on their anticoagulant potency was not significant and the O-acylation of 2-OH groups of 4-O-sulfated fucose units did not affect the anticoagulant activity.
Keywords: sea cucumber; fucosylated chondroitin sulfate; glycosaminoglycan; acylation; anticoagulant activity
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MDPI and ACS Style

Gao, N.; Wu, M.; Liu, S.; Lian, W.; Li, Z.; Zhao, J. Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber. Mar. Drugs 2012, 10, 1647-1661.

AMA Style

Gao N, Wu M, Liu S, Lian W, Li Z, Zhao J. Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber. Marine Drugs. 2012; 10(8):1647-1661.

Chicago/Turabian Style

Gao, Na; Wu, Mingyi; Liu, Shao; Lian, Wu; Li, Zi; Zhao, Jinhua. 2012. "Preparation and Characterization of O-Acylated Fucosylated Chondroitin Sulfate from Sea Cucumber." Mar. Drugs 10, no. 8: 1647-1661.

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