title: Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: insights into the sugar sequences with bioactivities.
abstract: Chondroitin sulfate (CS) chains regulate the development of the central nervous system in vertebrates and are linear polysaccharides consisting of variously sulfated repeating disaccharides, [-4GlcUAβ1-3GalNAcβ1-](n), where GlcUA and GalNAc represent D-glucuronic acid and N-acetyl-D-galactosamine, respectively. CS chains containing D-disaccharide units [GlcUA(2-O-sulfate)-GalNAc(6-O-sulfate)] are involved in the development of cerebellar Purkinje cells and neurite outgrowth-promoting activity through interaction with a neurotrophic factor, pleiotrophin, resulting in the regulation of signaling. In this study, to obtain further structural information on the CS chains containing d-disaccharide units involved in brain development, oligosaccharides containing D-units were isolated from a shark fin cartilage. Seven novel hexasaccharide sequences, ΔO-D-D, ΔA-D-D, ΔC-D-D, ΔE-A-D, ΔD-D-C, ΔE-D-D and ΔA-B-D, in addition to three previously reported sequences, ΔC-A-D, ΔC-D-C and ΔA-D-A, were isolated from a CS preparation of shark fin cartilage after exhaustive digestion with chondroitinase AC-I, which cannot act on the galactosaminidic linkages bound to D-units. The symbol Δ stands for a 4,5-unsaturated bond of uronic acids, whereas A, B, C, D, E and O represent [GlcUA-GalNAc(4-O-sulfate)], [GlcUA(2-O-sulfate)-GalNAc(4-O-sulfate)], [GlcUA-GalNAc(6-O-sulfate)], [GlcUA(2-O-sulfate)-GalNAc(6-O-sulfate)], [GlcUA-GalNAc(4-O-, 6-O-sulfate)] and [GlcUA-GalNAc], respectively. In binding studies using an anti-CS monoclonal antibody, MO-225, the epitopes of which are involved in cerebellar development in mammals, novel epitope structures, ΔA-D-A, ΔA-D-D and ΔA-B-D, were revealed. Hexasaccharides containing two consecutive D-units or a B-unit will be useful for the structural and functional analyses of CS chains particularly in the neuroglycobiological fields.
authors.affiliation: Faculty of Advanced Life Science, Graduate School of Life Science, Hokkaido University, Sapporo, Hokkaido, Japan.
authors.forename: Shuji
authors.initials: S
authors.lastname: Mizumoto
authors.forename: Saori
authors.initials: S
authors.lastname: Murakoshi
authors.forename: Kittiwan
authors.initials: K
authors.lastname: Kalayanamitra
authors.forename: Sarama Sathyaseelan
authors.initials: SS
authors.lastname: Deepa
authors.forename: Shigeyuki
authors.initials: S
authors.lastname: Fukui
authors.forename: Prachya
authors.initials: P
authors.lastname: Kongtawelert
authors.forename: Shuhei
authors.initials: S
authors.lastname: Yamada
authors.forename: Kazuyuki
authors.initials: K
authors.lastname: Sugahara
mesh_terms: D000116:Acetylgalactosamine / Q000737:chemistry / Q000378:metabolism; D058500:Animal Fins / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D002356:Cartilage / Q000737:chemistry / Q000276:immunology / Q000378:metabolism; D002809:Chondroitin Sulfates / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D002810:Chondroitinases and Chondroitin Lyases / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D000939:Epitopes / Q000276:immunology / Q000378:metabolism; D009414:Nerve Growth Factors / Q000737:chemistry / Q000276:immunology / Q000378:metabolism; D009844:Oligosaccharides / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D011485:Protein Binding / Q000276:immunology; D011689:Purkinje Cells / Q000378:metabolism / Q000502:physiology; D012754:Sharks; D013431:Sulfates / Q000276:immunology / Q000378:metabolism; D014574:Uronic Acids / Q000276:immunology / Q000378:metabolism
chemical_list: D000939:Epitopes; D009414:Nerve Growth Factors; D009844:Oligosaccharides; D013431:Sulfates; D014574:Uronic Acids; D002809:Chondroitin Sulfates; D002810:Chondroitinases and Chondroitin Lyases; D000116:Acetylgalactosamine