Electrochemical synthesis of the protected cyclic (1,3;1,6)-β-glucan dodecasaccharide
Automated electrochemical assembly is an electrochemical method to synthesise middle-sized molecules, including linear oligosaccharides, and some linear oligosaccharides can be electrochemically converted into the corresponding cyclic oligosaccharides effectively. In this study, the target cyclic ol...
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| Veröffentlicht in: | Faraday discussions 2023-10, Vol.247, p.59-69 |
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| creator | Shibuya, Akito Ishisaka, Yui Saito, Asuka Kato, Moeko Manmode, Sujit Komatsu, Hiroto Rahman, Md Azadur Sasaki, Norihiko Itoh, Toshiyuki Nokami, Toshiki |
| description | Automated electrochemical assembly is an electrochemical method to synthesise middle-sized molecules, including linear oligosaccharides, and some linear oligosaccharides can be electrochemically converted into the corresponding cyclic oligosaccharides effectively. In this study, the target cyclic oligosaccharide is a protected cyclic (1,3;1,6)-β-glucan dodecasaccharide, which consists of two types of glucose trisaccharides with β-(1,3)- and β-(1,6)-glycosidic linkages. The formation of the protected cyclic dodecasaccharide was confirmed by the electrochemical one-pot dimerisation-cyclisation of the semi-circular hexasaccharide. The yield of the protected cyclic dodecasaccharide was improved by using a stepwise synthesis
via
the linear dodecasaccharide.
A protected cyclic (1,3;1,6)-β-glucan dodecasaccharide was synthesized by the electrochemical one-pot dimerisation-cyclisation of a semi-circular hexasaccharide. |
| doi_str_mv | 10.1039/d3fd00045a |
| format | Article |
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via
the linear dodecasaccharide.
A protected cyclic (1,3;1,6)-β-glucan dodecasaccharide was synthesized by the electrochemical one-pot dimerisation-cyclisation of a semi-circular hexasaccharide.</description><identifier>ISSN: 1359-6640</identifier><identifier>EISSN: 1364-5498</identifier><identifier>DOI: 10.1039/d3fd00045a</identifier><identifier>PMID: 37466008</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>beta-Glucans - chemistry ; Chemical synthesis ; Dimerization ; Glucan ; Oligosaccharides ; Oligosaccharides - chemistry</subject><ispartof>Faraday discussions, 2023-10, Vol.247, p.59-69</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c296t-60c34d123f0150bf5ba37ae0a33312ea7e4cedc8e9c158ebd5101dac432cefda3</cites><orcidid>0000-0001-5447-4533</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37466008$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shibuya, Akito</creatorcontrib><creatorcontrib>Ishisaka, Yui</creatorcontrib><creatorcontrib>Saito, Asuka</creatorcontrib><creatorcontrib>Kato, Moeko</creatorcontrib><creatorcontrib>Manmode, Sujit</creatorcontrib><creatorcontrib>Komatsu, Hiroto</creatorcontrib><creatorcontrib>Rahman, Md Azadur</creatorcontrib><creatorcontrib>Sasaki, Norihiko</creatorcontrib><creatorcontrib>Itoh, Toshiyuki</creatorcontrib><creatorcontrib>Nokami, Toshiki</creatorcontrib><title>Electrochemical synthesis of the protected cyclic (1,3;1,6)-β-glucan dodecasaccharide</title><title>Faraday discussions</title><addtitle>Faraday Discuss</addtitle><description>Automated electrochemical assembly is an electrochemical method to synthesise middle-sized molecules, including linear oligosaccharides, and some linear oligosaccharides can be electrochemically converted into the corresponding cyclic oligosaccharides effectively. In this study, the target cyclic oligosaccharide is a protected cyclic (1,3;1,6)-β-glucan dodecasaccharide, which consists of two types of glucose trisaccharides with β-(1,3)- and β-(1,6)-glycosidic linkages. The formation of the protected cyclic dodecasaccharide was confirmed by the electrochemical one-pot dimerisation-cyclisation of the semi-circular hexasaccharide. The yield of the protected cyclic dodecasaccharide was improved by using a stepwise synthesis
via
the linear dodecasaccharide.
A protected cyclic (1,3;1,6)-β-glucan dodecasaccharide was synthesized by the electrochemical one-pot dimerisation-cyclisation of a semi-circular hexasaccharide.</description><subject>beta-Glucans - chemistry</subject><subject>Chemical synthesis</subject><subject>Dimerization</subject><subject>Glucan</subject><subject>Oligosaccharides</subject><subject>Oligosaccharides - chemistry</subject><issn>1359-6640</issn><issn>1364-5498</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpd0c1Kw0AQB_BFFFurF-9KwEuVRvcrmwRPpR8qFLyo17CdndiUtKm7yaGv5YP4TG5treBpBubHMPyHkHNGbxkV6Z0RuaGUykgfkDYTSoaRTJPDTR-loVKStsiJc3NvlJ8ek5aIpVKUJm3yNioRalvBDBcF6DJw62U9Q1e4oMoD3wUrW9WeoAlgDWUBQZf1xD3rqevw6zN8LxvQy8BUBkE7DTDTtjB4So5yXTo829UOeR2PXgaP4eT54WnQn4TAU1WHioKQhnGRUxbRaR5NtYg1Ui2EYBx1jBLQQIIpsCjBqYkYZUaDFBwwN1p0SHe711_50aCrs0XhAMtSL7FqXMYTkcaS05h6evWPzqvGLv11XiU-D8458-pmq8BWzlnMs5UtFtquM0azTdrZUIyHP2n3Pb7crWymCzR7-huvBxdbYB3sp3_vEt8CEYNk</recordid><startdate>20231031</startdate><enddate>20231031</enddate><creator>Shibuya, Akito</creator><creator>Ishisaka, Yui</creator><creator>Saito, Asuka</creator><creator>Kato, Moeko</creator><creator>Manmode, Sujit</creator><creator>Komatsu, Hiroto</creator><creator>Rahman, Md Azadur</creator><creator>Sasaki, Norihiko</creator><creator>Itoh, Toshiyuki</creator><creator>Nokami, Toshiki</creator><general>Royal Society of Chemistry</general><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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5447-4533</orcidid></search><sort><creationdate>20231031</creationdate><title>Electrochemical synthesis of the protected cyclic (1,3;1,6)-β-glucan dodecasaccharide</title><author>Shibuya, Akito ; Ishisaka, Yui ; Saito, Asuka ; Kato, Moeko ; Manmode, Sujit ; Komatsu, Hiroto ; Rahman, Md Azadur ; Sasaki, Norihiko ; Itoh, Toshiyuki ; Nokami, Toshiki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-60c34d123f0150bf5ba37ae0a33312ea7e4cedc8e9c158ebd5101dac432cefda3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>beta-Glucans - chemistry</topic><topic>Chemical synthesis</topic><topic>Dimerization</topic><topic>Glucan</topic><topic>Oligosaccharides</topic><topic>Oligosaccharides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shibuya, Akito</creatorcontrib><creatorcontrib>Ishisaka, Yui</creatorcontrib><creatorcontrib>Saito, Asuka</creatorcontrib><creatorcontrib>Kato, Moeko</creatorcontrib><creatorcontrib>Manmode, Sujit</creatorcontrib><creatorcontrib>Komatsu, Hiroto</creatorcontrib><creatorcontrib>Rahman, Md Azadur</creatorcontrib><creatorcontrib>Sasaki, Norihiko</creatorcontrib><creatorcontrib>Itoh, Toshiyuki</creatorcontrib><creatorcontrib>Nokami, Toshiki</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><jtitle>Faraday discussions</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shibuya, Akito</au><au>Ishisaka, Yui</au><au>Saito, Asuka</au><au>Kato, Moeko</au><au>Manmode, Sujit</au><au>Komatsu, Hiroto</au><au>Rahman, Md Azadur</au><au>Sasaki, Norihiko</au><au>Itoh, Toshiyuki</au><au>Nokami, Toshiki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical synthesis of the protected cyclic (1,3;1,6)-β-glucan dodecasaccharide</atitle><jtitle>Faraday discussions</jtitle><addtitle>Faraday Discuss</addtitle><date>2023-10-31</date><risdate>2023</risdate><volume>247</volume><spage>59</spage><epage>69</epage><pages>59-69</pages><issn>1359-6640</issn><eissn>1364-5498</eissn><abstract>Automated electrochemical assembly is an electrochemical method to synthesise middle-sized molecules, including linear oligosaccharides, and some linear oligosaccharides can be electrochemically converted into the corresponding cyclic oligosaccharides effectively. In this study, the target cyclic oligosaccharide is a protected cyclic (1,3;1,6)-β-glucan dodecasaccharide, which consists of two types of glucose trisaccharides with β-(1,3)- and β-(1,6)-glycosidic linkages. The formation of the protected cyclic dodecasaccharide was confirmed by the electrochemical one-pot dimerisation-cyclisation of the semi-circular hexasaccharide. The yield of the protected cyclic dodecasaccharide was improved by using a stepwise synthesis
via
the linear dodecasaccharide.
A protected cyclic (1,3;1,6)-β-glucan dodecasaccharide was synthesized by the electrochemical one-pot dimerisation-cyclisation of a semi-circular hexasaccharide.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37466008</pmid><doi>10.1039/d3fd00045a</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-5447-4533</orcidid></addata></record> |
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| ispartof | Faraday discussions, 2023-10, Vol.247, p.59-69 |
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| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | beta-Glucans - chemistry Chemical synthesis Dimerization Glucan Oligosaccharides Oligosaccharides - chemistry |
| title | Electrochemical synthesis of the protected cyclic (1,3;1,6)-β-glucan dodecasaccharide |
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