TY - JOUR
T1 - Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage
T2 - Insights into the sugar sequences with bioactivities
AU - Mizumoto, Shuji
AU - Murakoshi, Saori
AU - Kalayanamitra, Kittiwan
AU - Deepa, Sarama Sathyaseelan
AU - Fukui, Shigeyuki
AU - Kongtawelert, Prachya
AU - Yamada, Shuhei
AU - Sugahara, Kazuyuki
N1 - Funding Information:
This work was supported in part by Grants-in-aid for Scientific Research on Innovative Areas (24110501) (to K.S.) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT), Japan–Thailand Research Cooperative Program (to K.S.) from the Japan Society for the Promotion of Science (JSPS) and Young Scientists (B) 23790066 (to S.M.) from JSPS. K.K. was a recipient of The Royal Golden Jubilee (RGJ) scholarship from Thailand during her work at Kobe Pharmaceutical University.
PY - 2013/2
Y1 - 2013/2
N2 - 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.
AB - 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.
KW - brain development
KW - chondroitin sulfate
KW - hexasaccharide
KW - monoclonal antibody
KW - neuritogenesis
UR - http://www.scopus.com/inward/record.url?scp=84871948536&partnerID=8YFLogxK
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U2 - 10.1093/glycob/cws137
DO - 10.1093/glycob/cws137
M3 - Article
C2 - 23019154
AN - SCOPUS:84871948536
VL - 23
SP - 155
EP - 168
JO - Glycobiology
JF - Glycobiology
SN - 0959-6658
IS - 2
ER -