Structure of fucose branches in the glycosaminoglycan from the body wall of the sea cucumber Stichopus japonicus.
Fucose-branched chondroitin sulfate E was prepared from the body wall of sea cucumber Stichopus japonicus. The purified glycosaminoglycan (GAG) was chemically desulfated, followed by carboxyl reduction. Intact, desulfated, and desulfated/carboxyl-reduced GAG fractions were subjected to per-O-methylation. GC-MS analyses of the resultant partially methylated alditol acetates demonstrated that the fucose branch is formed by two fucopyranosyl residues linked glycosidically through position (1-->3), and that the fucose branch and glucuronic acid are almost equimolar. In addition, it was elucidated that about 20% of the branches stretch from O-3 position of a glucuronic acid moiety of the core chondroitin sulfate polymer, while remaining fucose branches are postulated to protrude from O-4 and/or O-6 position(s) of a N-acetylgalactosamine moiety. This fucose branch was also confirmed to be highly sulfated according to six kinds of substitution pattern in methylation analysis.
Kariya
Y
Y
Tokyo Research Institute, Seikagaku Corporation, Tokyo, Japan.
Watabe
S
S
Kyogashima
M
M
Ishihara
M
M
Ishii
T
T
D000116:Acetylgalactosamine / Q000032:analysis; D000818:Animals; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002809:Chondroitin Sulfates / Q000737:chemistry / Q000302:isolation & purification; D005643:Fucose / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000032:analysis; D005965:Glucuronates / Q000032:analysis; D020723:Glucuronic Acid; D006025:Glycosaminoglycans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D012616:Sea Cucumbers / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry
D005965:Glucuronates; D006025:Glycosaminoglycans; D013431:Sulfates; D005643:Fucose; D020723:Glucuronic Acid; D002809:Chondroitin Sulfates; D005947:Glucose; D000116:Acetylgalactosamine