Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities

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, r...

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Main Authors: Shuji Mizumoto, Saori Murakoshi, Kittiwan Kalayanamitra, Sarama Sathyaseelan Deepa, Shigeyuki Fukui, Prachya Kongtawelert, Shuhei Yamada, Kazuyuki Sugahara
Format: Journal
Published: 2018
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http://cmuir.cmu.ac.th/jspui/handle/6653943832/48140
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spelling th-cmuir.6653943832-481402018-04-25T08:48:08Z Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities Shuji Mizumoto Saori Murakoshi Kittiwan Kalayanamitra Sarama Sathyaseelan Deepa Shigeyuki Fukui Prachya Kongtawelert Shuhei Yamada Kazuyuki Sugahara 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. © 2012 The Author. 2018-04-25T08:48:08Z 2018-04-25T08:48:08Z 2013-02-01 Journal 14602423 09596658 2-s2.0-84871948536 10.1093/glycob/cws137 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84871948536&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/48140
institution Chiang Mai University
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description 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. © 2012 The Author.
format Journal
author Shuji Mizumoto
Saori Murakoshi
Kittiwan Kalayanamitra
Sarama Sathyaseelan Deepa
Shigeyuki Fukui
Prachya Kongtawelert
Shuhei Yamada
Kazuyuki Sugahara
spellingShingle Shuji Mizumoto
Saori Murakoshi
Kittiwan Kalayanamitra
Sarama Sathyaseelan Deepa
Shigeyuki Fukui
Prachya Kongtawelert
Shuhei Yamada
Kazuyuki Sugahara
Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities
author_facet Shuji Mizumoto
Saori Murakoshi
Kittiwan Kalayanamitra
Sarama Sathyaseelan Deepa
Shigeyuki Fukui
Prachya Kongtawelert
Shuhei Yamada
Kazuyuki Sugahara
author_sort Shuji Mizumoto
title Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities
title_short Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities
title_full Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities
title_fullStr Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities
title_full_unstemmed Highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: Insights into the sugar sequences with bioactivities
title_sort highly sulfated hexasaccharide sequences isolated from chondroitin sulfate of shark fin cartilage: insights into the sugar sequences with bioactivities
publishDate 2018
url https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84871948536&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/48140
_version_ 1681423194328662016