Chemical Synthesis of an Orthogonally Protected 5,7-Diamino-3,5,7,9-tetradeoxy‑d‑glycero‑l‑gluco-2-nonulosonic Acid from N‑Acetylneuraminic Acid
Bacterial nonulosonic acids (NulOs), which feature a nine-carbon backbone, are associated with the biological functions of bacterial glycans. Here, an orthogonally protected 5-amino-7-azido-3,5,7,9-tetradeoxy-d-glycero-l-gluco-2-nonulosonic acid related to Fusobacterium nucleatum ATCC 23726 NulO was...
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| Veröffentlicht in: | Organic letters 2024-06, Vol.26 (24), p.5215-5219 |
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| creator | Ding, Meiru Sun, Wenbin Tian, Guangzong Zou, Xiaopeng Hu, Jing Qin, Chunjun Yin, Jian |
| description | Bacterial nonulosonic acids (NulOs), which feature a nine-carbon backbone, are associated with the biological functions of bacterial glycans. Here, an orthogonally protected 5-amino-7-azido-3,5,7,9-tetradeoxy-d-glycero-l-gluco-2-nonulosonic acid related to Fusobacterium nucleatum ATCC 23726 NulO was synthesized from N-acetylneuraminic acid with sequential performance of C5,7 azidation, C9 deoxygenation, C4 epimerization, and N5,7 differentiation. The C5 azido group in the obtained 5,7-diazido-NulO can be regioselectively reduced to differentiate the two amino groups. |
| doi_str_mv | 10.1021/acs.orglett.4c01861 |
| format | Article |
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The C5 azido group in the obtained 5,7-diazido-NulO can be regioselectively reduced to differentiate the two amino groups.</description><subject>Fusobacterium nucleatum</subject><subject>polysaccharides</subject><subject>regioselectivity</subject><subject>sialic acid</subject><subject>synthesis</subject><issn>1523-7060</issn><issn>1523-7052</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkc9u3CAQh1HVqEnTPkGlimMPywbMgvFxtf0rRUmltmeLxcOuIwwpYKm-9RV6zePlScp2nRybA2IGvt_M4UPoDaNLRit2oU1ahrhzkPNyZShTkj1DZ0xUnNRUVM8fa0lP0cuUbihl5aV5gU65KrCs6zN0t9nD0Bvt8LfJ5z2kPuFgsfb4OuZ92AWvnZvw1xgymAwdFouavO_10PtA-KJ0i4ZkyFF3EH5N97__dOXs3GQghlK5f91oAqmID350IQXfG7w2fYdtDAO-KsTaQJ6chzEeBs_fr9CJ1S7B6_k-Rz8-fvi--Uwurz992awvieaVysTIGioJiivLtlo3vOoEdJTVSoO2zHDNrWhEJdTWCmGsYZxbKlYSGrFltOPn6N1x7m0MP0dIuR36ZMA57SGMqeVMcLlaSUqfRmlNFZeNYgXlR9TEkFIE297GftBxahltD_7a4q-d_bWzv5J6Oy8YtwN0j5kHYQW4OAKH9E0YY_GT_jvyL-dur64</recordid><startdate>20240621</startdate><enddate>20240621</enddate><creator>Ding, Meiru</creator><creator>Sun, Wenbin</creator><creator>Tian, Guangzong</creator><creator>Zou, Xiaopeng</creator><creator>Hu, Jing</creator><creator>Qin, Chunjun</creator><creator>Yin, Jian</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0009-0004-8974-5507</orcidid><orcidid>https://orcid.org/0000-0002-2284-1666</orcidid><orcidid>https://orcid.org/0000-0003-3288-7067</orcidid></search><sort><creationdate>20240621</creationdate><title>Chemical Synthesis of an Orthogonally Protected 5,7-Diamino-3,5,7,9-tetradeoxy‑d‑glycero‑l‑gluco-2-nonulosonic Acid from N‑Acetylneuraminic Acid</title><author>Ding, Meiru ; Sun, Wenbin ; Tian, Guangzong ; Zou, Xiaopeng ; Hu, Jing ; Qin, Chunjun ; Yin, Jian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a328t-c67e26e838f1baa932d5ed0178aeaf1c3a3f595258bf55cfc133f0546e95b10d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Fusobacterium nucleatum</topic><topic>polysaccharides</topic><topic>regioselectivity</topic><topic>sialic acid</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ding, Meiru</creatorcontrib><creatorcontrib>Sun, Wenbin</creatorcontrib><creatorcontrib>Tian, Guangzong</creatorcontrib><creatorcontrib>Zou, Xiaopeng</creatorcontrib><creatorcontrib>Hu, Jing</creatorcontrib><creatorcontrib>Qin, Chunjun</creatorcontrib><creatorcontrib>Yin, Jian</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ding, Meiru</au><au>Sun, Wenbin</au><au>Tian, Guangzong</au><au>Zou, Xiaopeng</au><au>Hu, Jing</au><au>Qin, Chunjun</au><au>Yin, Jian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical Synthesis of an Orthogonally Protected 5,7-Diamino-3,5,7,9-tetradeoxy‑d‑glycero‑l‑gluco-2-nonulosonic Acid from N‑Acetylneuraminic Acid</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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The C5 azido group in the obtained 5,7-diazido-NulO can be regioselectively reduced to differentiate the two amino groups.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38861677</pmid><doi>10.1021/acs.orglett.4c01861</doi><tpages>5</tpages><orcidid>https://orcid.org/0009-0004-8974-5507</orcidid><orcidid>https://orcid.org/0000-0002-2284-1666</orcidid><orcidid>https://orcid.org/0000-0003-3288-7067</orcidid></addata></record> |
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| language | eng |
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| source | ACS Publications |
| subjects | Fusobacterium nucleatum polysaccharides regioselectivity sialic acid synthesis |
| title | Chemical Synthesis of an Orthogonally Protected 5,7-Diamino-3,5,7,9-tetradeoxy‑d‑glycero‑l‑gluco-2-nonulosonic Acid from N‑Acetylneuraminic Acid |
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