Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd-numbered oligosaccharides
Sulfated galactan κ-carrageenan is a linear polysaccharide with a repeating disaccharide sequence of alternating 4-sulfated 3-linked galactose and 4-linked 3,6-anhydrogalactose units. In contrast to many examples of chemical hydrolysis of polysaccharides, mild acid treatment of κ-carrageenan resulte...
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| Veröffentlicht in: | The FEBS journal 2009-04, Vol.276 (7), p.2125-2137 |
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| creator | Yang, Bo Yu, Guangli Zhao, Xia Jiao, Guangling Ren, Sumei Chai, Wengang |
| description | Sulfated galactan κ-carrageenan is a linear polysaccharide with a repeating disaccharide sequence of alternating 4-sulfated 3-linked galactose and 4-linked 3,6-anhydrogalactose units. In contrast to many examples of chemical hydrolysis of polysaccharides, mild acid treatment of κ-carrageenan resulted in facile and highly specific cleavage. In this article, we report the identification, by various MS and chromatographic techniques, of an unexpected series of exclusively odd-numbered oligosaccharide fragments from its hydrolytic products. Detailed sequence analysis of the products indicated that all the oligosaccharide fragments have the 4-sulfated 3-linked galactose residues at both the reducing and the nonreducing ends. Further detailed investigation and analysis suggested that these odd-numbered oligosaccharides were derived from two-step cleavages of the glycosidic bonds on either sides of the 3,6-anhydrogalactose residues. Neutral galactan agarose also contains 3,6-anhydrogalactose and has a similar backbone sequence, and exhibited similar results upon mild acid hydrolysis. It is highly unusual to obtain exclusively odd-numbered oligosaccharides from polysaccharides composed of ordered disaccharide repeats. |
| doi_str_mv | 10.1111/j.1742-4658.2009.06947.x |
| format | Article |
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In contrast to many examples of chemical hydrolysis of polysaccharides, mild acid treatment of κ-carrageenan resulted in facile and highly specific cleavage. In this article, we report the identification, by various MS and chromatographic techniques, of an unexpected series of exclusively odd-numbered oligosaccharide fragments from its hydrolytic products. Detailed sequence analysis of the products indicated that all the oligosaccharide fragments have the 4-sulfated 3-linked galactose residues at both the reducing and the nonreducing ends. Further detailed investigation and analysis suggested that these odd-numbered oligosaccharides were derived from two-step cleavages of the glycosidic bonds on either sides of the 3,6-anhydrogalactose residues. Neutral galactan agarose also contains 3,6-anhydrogalactose and has a similar backbone sequence, and exhibited similar results upon mild acid hydrolysis. It is highly unusual to obtain exclusively odd-numbered oligosaccharides from polysaccharides composed of ordered disaccharide repeats.</description><identifier>ISSN: 1742-464X</identifier><identifier>EISSN: 1742-4658</identifier><identifier>DOI: 10.1111/j.1742-4658.2009.06947.x</identifier><identifier>PMID: 19292880</identifier><language>eng</language><publisher>Oxford, UK: Oxford, UK : Blackwell Publishing Ltd</publisher><subject>acid hydrolysis ; Acids ; agarose ; Biochemistry ; Carbohydrate Sequence ; carrageenan ; Carrageenan - chemistry ; Chemical bonds ; Chemical reactions ; Disaccharides - chemistry ; Galactans - chemistry ; Hydrolysis ; mass spectrometry ; Molecular Sequence Data ; Molecular structure ; Oligosaccharides - analysis ; Oligosaccharides - chemistry ; polysaccharide ; Polysaccharides - chemistry ; Sulfates - chemistry ; Tandem Mass Spectrometry</subject><ispartof>The FEBS journal, 2009-04, Vol.276 (7), p.2125-2137</ispartof><rights>2009 The Authors Journal compilation © 2009 FEBS</rights><rights>Journal compilation © 2009 Federation of European Biochemical Societies</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5007-923c67880c58f2d6f3efd8150514def6401a1b6cc4ca89a402152f177f0703c33</citedby><cites>FETCH-LOGICAL-c5007-923c67880c58f2d6f3efd8150514def6401a1b6cc4ca89a402152f177f0703c33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fj.1742-4658.2009.06947.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fj.1742-4658.2009.06947.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,1428,27905,27906,45555,45556,46390,46814</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19292880$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yang, Bo</creatorcontrib><creatorcontrib>Yu, Guangli</creatorcontrib><creatorcontrib>Zhao, Xia</creatorcontrib><creatorcontrib>Jiao, Guangling</creatorcontrib><creatorcontrib>Ren, Sumei</creatorcontrib><creatorcontrib>Chai, Wengang</creatorcontrib><title>Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd-numbered oligosaccharides</title><title>The FEBS journal</title><addtitle>FEBS J</addtitle><description>Sulfated galactan κ-carrageenan is a linear polysaccharide with a repeating disaccharide sequence of alternating 4-sulfated 3-linked galactose and 4-linked 3,6-anhydrogalactose units. In contrast to many examples of chemical hydrolysis of polysaccharides, mild acid treatment of κ-carrageenan resulted in facile and highly specific cleavage. In this article, we report the identification, by various MS and chromatographic techniques, of an unexpected series of exclusively odd-numbered oligosaccharide fragments from its hydrolytic products. Detailed sequence analysis of the products indicated that all the oligosaccharide fragments have the 4-sulfated 3-linked galactose residues at both the reducing and the nonreducing ends. Further detailed investigation and analysis suggested that these odd-numbered oligosaccharides were derived from two-step cleavages of the glycosidic bonds on either sides of the 3,6-anhydrogalactose residues. Neutral galactan agarose also contains 3,6-anhydrogalactose and has a similar backbone sequence, and exhibited similar results upon mild acid hydrolysis. It is highly unusual to obtain exclusively odd-numbered oligosaccharides from polysaccharides composed of ordered disaccharide repeats.</description><subject>acid hydrolysis</subject><subject>Acids</subject><subject>agarose</subject><subject>Biochemistry</subject><subject>Carbohydrate Sequence</subject><subject>carrageenan</subject><subject>Carrageenan - chemistry</subject><subject>Chemical bonds</subject><subject>Chemical reactions</subject><subject>Disaccharides - chemistry</subject><subject>Galactans - chemistry</subject><subject>Hydrolysis</subject><subject>mass spectrometry</subject><subject>Molecular Sequence Data</subject><subject>Molecular structure</subject><subject>Oligosaccharides - analysis</subject><subject>Oligosaccharides - chemistry</subject><subject>polysaccharide</subject><subject>Polysaccharides - chemistry</subject><subject>Sulfates - chemistry</subject><subject>Tandem Mass Spectrometry</subject><issn>1742-464X</issn><issn>1742-4658</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkc9u1DAQhyMEon_gFcDiwC1h7DhOckGCqgWkIg6lEjfLa08Sr5x4sRO6-1Y8YpPdVYu4gC-2xt98o9EvSQiFjM7n3TqjJWcpF0WVMYA6A1HzMts-SU4fPp4-vPmPk-QsxjVAXvC6fp6c0JrVrKrgNPn9FXWnBht74hvSW2eI0taQbmeCd7to41JvlVN6VAPZLDWl55ZgDUZyZ8eOdLbt3I74YDCgIcY-EiTgBtUYiUNl7NCS0RNFtO83DkckEYPF_QTcajdF-wsXkTHpMPWrvc072_o_Rr5InjXKRXx5vM-T26vL7xef0-tvn75cfLhOdQFQpjXLtSjnFXVRNcyIJsfGVLSAgnKDjeBAFV0JrblWVa04MFqwhpZlAyXkOs_Pk7cH7yb4nxPGUfY2anRODeinKEUJHITg_wQZBVFQxmbwzV_g2k9hmJeQDDhlJdtD1QHSwccYsJGbYHsVdpKCXLKXa7nEKpeI5ZK93Gcvt3Prq6N_WvVoHhuPYc_A-wNwZx3u_lssry4_3izPWfD6IGiUl6oNNsrbGwY0ByqggDLP7wGemMoe</recordid><startdate>200904</startdate><enddate>200904</enddate><creator>Yang, Bo</creator><creator>Yu, Guangli</creator><creator>Zhao, Xia</creator><creator>Jiao, Guangling</creator><creator>Ren, Sumei</creator><creator>Chai, Wengang</creator><general>Oxford, UK : Blackwell Publishing Ltd</general><general>Blackwell Publishing Ltd</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>M7N</scope><scope>P64</scope><scope>RC3</scope><scope>F1W</scope><scope>H96</scope><scope>L.G</scope><scope>7X8</scope></search><sort><creationdate>200904</creationdate><title>Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd-numbered oligosaccharides</title><author>Yang, Bo ; Yu, Guangli ; Zhao, Xia ; Jiao, Guangling ; Ren, Sumei ; Chai, Wengang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5007-923c67880c58f2d6f3efd8150514def6401a1b6cc4ca89a402152f177f0703c33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>acid hydrolysis</topic><topic>Acids</topic><topic>agarose</topic><topic>Biochemistry</topic><topic>Carbohydrate Sequence</topic><topic>carrageenan</topic><topic>Carrageenan - chemistry</topic><topic>Chemical bonds</topic><topic>Chemical reactions</topic><topic>Disaccharides - chemistry</topic><topic>Galactans - chemistry</topic><topic>Hydrolysis</topic><topic>mass spectrometry</topic><topic>Molecular Sequence Data</topic><topic>Molecular structure</topic><topic>Oligosaccharides - analysis</topic><topic>Oligosaccharides - chemistry</topic><topic>polysaccharide</topic><topic>Polysaccharides - chemistry</topic><topic>Sulfates - chemistry</topic><topic>Tandem Mass Spectrometry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yang, Bo</creatorcontrib><creatorcontrib>Yu, Guangli</creatorcontrib><creatorcontrib>Zhao, Xia</creatorcontrib><creatorcontrib>Jiao, Guangling</creatorcontrib><creatorcontrib>Ren, Sumei</creatorcontrib><creatorcontrib>Chai, Wengang</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 2: Ocean Technology, Policy & Non-Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>MEDLINE - Academic</collection><jtitle>The FEBS journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yang, Bo</au><au>Yu, Guangli</au><au>Zhao, Xia</au><au>Jiao, Guangling</au><au>Ren, Sumei</au><au>Chai, Wengang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd-numbered oligosaccharides</atitle><jtitle>The FEBS journal</jtitle><addtitle>FEBS J</addtitle><date>2009-04</date><risdate>2009</risdate><volume>276</volume><issue>7</issue><spage>2125</spage><epage>2137</epage><pages>2125-2137</pages><issn>1742-464X</issn><eissn>1742-4658</eissn><abstract>Sulfated galactan κ-carrageenan is a linear polysaccharide with a repeating disaccharide sequence of alternating 4-sulfated 3-linked galactose and 4-linked 3,6-anhydrogalactose units. In contrast to many examples of chemical hydrolysis of polysaccharides, mild acid treatment of κ-carrageenan resulted in facile and highly specific cleavage. In this article, we report the identification, by various MS and chromatographic techniques, of an unexpected series of exclusively odd-numbered oligosaccharide fragments from its hydrolytic products. Detailed sequence analysis of the products indicated that all the oligosaccharide fragments have the 4-sulfated 3-linked galactose residues at both the reducing and the nonreducing ends. Further detailed investigation and analysis suggested that these odd-numbered oligosaccharides were derived from two-step cleavages of the glycosidic bonds on either sides of the 3,6-anhydrogalactose residues. Neutral galactan agarose also contains 3,6-anhydrogalactose and has a similar backbone sequence, and exhibited similar results upon mild acid hydrolysis. It is highly unusual to obtain exclusively odd-numbered oligosaccharides from polysaccharides composed of ordered disaccharide repeats.</abstract><cop>Oxford, UK</cop><pub>Oxford, UK : Blackwell Publishing Ltd</pub><pmid>19292880</pmid><doi>10.1111/j.1742-4658.2009.06947.x</doi><tpages>13</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | acid hydrolysis Acids agarose Biochemistry Carbohydrate Sequence carrageenan Carrageenan - chemistry Chemical bonds Chemical reactions Disaccharides - chemistry Galactans - chemistry Hydrolysis mass spectrometry Molecular Sequence Data Molecular structure Oligosaccharides - analysis Oligosaccharides - chemistry polysaccharide Polysaccharides - chemistry Sulfates - chemistry Tandem Mass Spectrometry |
| title | Mechanism of mild acid hydrolysis of galactan polysaccharides with highly ordered disaccharide repeats leading to a complete series of exclusively odd-numbered oligosaccharides |
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