Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues
A glucoronic acid-containing trisaccharide related to the antithrombin-binding DEFGH domain of heparin and its methanesulfonic acid analogues were synthesized. Trisaccharides without sulfonic acid content or possessing a sulfonatomethyl moiety at position 2 or 6 of unit F were prepared in high yield...
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| Veröffentlicht in: | Tetrahedron 2012-09, Vol.68 (36), p.7386-7399 |
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| container_issue | 36 |
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| container_title | Tetrahedron |
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| creator | Lázár, László Mező, Erika Herczeg, Mihály Lipták, András Antus, Sándor Borbás, Anikó |
| description | A glucoronic acid-containing trisaccharide related to the antithrombin-binding DEFGH domain of heparin and its methanesulfonic acid analogues were synthesized. Trisaccharides without sulfonic acid content or possessing a sulfonatomethyl moiety at position 2 or 6 of unit F were prepared in high yields by [DE+F] couplings using the same disaccharide uronate donor, respectively. Synthesis of the trisaccharide with a 3-deoxy-3-sulfonatomethyl function was accomplished in three different pathways, from which a [D+EF] coupling and applying a non-oxidized precursor of the glucuronic acid afforded the trisaccharide in the highest yield.
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| doi_str_mv | 10.1016/j.tet.2012.06.081 |
| format | Article |
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[Display omitted]</description><subject>Blood coagulation</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Couplings</subject><subject>d-Glucuronic acid</subject><subject>Exact sciences and technology</subject><subject>Glycosylation</subject><subject>Heparinoid trisaccharides</subject><subject>Heparins</subject><subject>Joining</subject><subject>Organic chemistry</subject><subject>Pathways</subject><subject>Precursors</subject><subject>Preparations and properties</subject><subject>Sulfonatomethyl analogues</subject><subject>Sulfonic acid</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kM1uFDEQhC0EEkvIA-Q2FyQuM7R_xvGKE4oIIEXiADlbHrsn26tZe7G9SHkFnjoebeDIodV9-KpKXYxdcRg4cP1hP1SsgwAuBtADGP6CbbjSqh8V1y_ZBkBBr0DAa_amlD0AcC7khv358RjrDguVLs1du7qYYp8xnDzFhw5j6Gqm4rzfuUwB_1IuVqq7nA4Txb5NWOmQDo7iiuzw2PDYsNBRLd1EiUoqFTP5rpyWOcV2OE-hIW5JDycsb9mr2S0FL5_3Bbu__fzz5mt_9_3Lt5tPd72XGmq_HQNq5Y0a3eQdyIAoIRgpZkTjPYRx2gaYleJbw2HrjJukmbzSzoxcKJAX7P3Z95jTr5Zb7YGKx2VxEdOpWH6tlDZCqrGh_Iz6nErJONtjpoPLj5aDXXu3e9t6t2vvFrRtvTfNu2d7V7xb5uyip_JPKLQAeQ2r98czh-3X34TZFk8YPQbK6KsNif6T8gQpWJsv</recordid><startdate>20120909</startdate><enddate>20120909</enddate><creator>Lázár, László</creator><creator>Mező, Erika</creator><creator>Herczeg, Mihály</creator><creator>Lipták, András</creator><creator>Antus, Sándor</creator><creator>Borbás, Anikó</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20120909</creationdate><title>Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues</title><author>Lázár, László ; Mező, Erika ; Herczeg, Mihály ; Lipták, András ; Antus, Sándor ; Borbás, Anikó</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-95de64c845abca03dee30d832fee8cc0d5b9d0f44198109a8ab38bc46a8512403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Blood coagulation</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Couplings</topic><topic>d-Glucuronic acid</topic><topic>Exact sciences and technology</topic><topic>Glycosylation</topic><topic>Heparinoid trisaccharides</topic><topic>Heparins</topic><topic>Joining</topic><topic>Organic chemistry</topic><topic>Pathways</topic><topic>Precursors</topic><topic>Preparations and properties</topic><topic>Sulfonatomethyl analogues</topic><topic>Sulfonic acid</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lázár, László</creatorcontrib><creatorcontrib>Mező, Erika</creatorcontrib><creatorcontrib>Herczeg, Mihály</creatorcontrib><creatorcontrib>Lipták, András</creatorcontrib><creatorcontrib>Antus, Sándor</creatorcontrib><creatorcontrib>Borbás, Anikó</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lázár, László</au><au>Mező, Erika</au><au>Herczeg, Mihály</au><au>Lipták, András</au><au>Antus, Sándor</au><au>Borbás, Anikó</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues</atitle><jtitle>Tetrahedron</jtitle><date>2012-09-09</date><risdate>2012</risdate><volume>68</volume><issue>36</issue><spage>7386</spage><epage>7399</epage><pages>7386-7399</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><coden>TETRAB</coden><abstract>A glucoronic acid-containing trisaccharide related to the antithrombin-binding DEFGH domain of heparin and its methanesulfonic acid analogues were synthesized. Trisaccharides without sulfonic acid content or possessing a sulfonatomethyl moiety at position 2 or 6 of unit F were prepared in high yields by [DE+F] couplings using the same disaccharide uronate donor, respectively. Synthesis of the trisaccharide with a 3-deoxy-3-sulfonatomethyl function was accomplished in three different pathways, from which a [D+EF] coupling and applying a non-oxidized precursor of the glucuronic acid afforded the trisaccharide in the highest yield.
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| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2012-09, Vol.68 (36), p.7386-7399 |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Blood coagulation Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Couplings d-Glucuronic acid Exact sciences and technology Glycosylation Heparinoid trisaccharides Heparins Joining Organic chemistry Pathways Precursors Preparations and properties Sulfonatomethyl analogues Sulfonic acid Synthesis Tetrahedrons |
| title | Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues |
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