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Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers
The proposed diastereoisomers (1 a–d) together with their C8′‐epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to b...
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| Published in: | Angewandte Chemie International Edition 2018-03, Vol.57 (11), p.2884-2888 |
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| Main Authors: | , , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c4769-1c136b0e592e7380f212f54482af0dca88a3647430709f9e554b9c483d7d7db33 |
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| container_end_page | 2888 |
| container_issue | 11 |
| container_start_page | 2884 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 57 |
| creator | Wang, Shengyang Sun, Jiansong Zhang, Qingju Cao, Xin Zhao, Yachen Tang, Gongli Yu, Biao |
| description | The proposed diastereoisomers (1 a–d) together with their C8′‐epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio‐ and stereocontrolled gold(I)‐catalyzed N‐glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.
All in the configuration: The proposed diastereoisomers and the relevant C8′ epimers of amipurimycin, a unique peptidyl nucleoside antibiotic, have been synthesized for the first time. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be in fact of opposite configuration. |
| doi_str_mv | 10.1002/anie.201800169 |
| format | article |
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All in the configuration: The proposed diastereoisomers and the relevant C8′ epimers of amipurimycin, a unique peptidyl nucleoside antibiotic, have been synthesized for the first time. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be in fact of opposite configuration.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201800169</identifier><identifier>PMID: 29356246</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Amino acids ; Antibiotics ; Configurations ; Diastereoisomers ; Fungicides ; Glycosylation ; Gold ; natural products ; NMR ; Nuclear magnetic resonance ; Nucleosides ; Sugar</subject><ispartof>Angewandte Chemie International Edition, 2018-03, Vol.57 (11), p.2884-2888</ispartof><rights>2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4769-1c136b0e592e7380f212f54482af0dca88a3647430709f9e554b9c483d7d7db33</citedby><cites>FETCH-LOGICAL-c4769-1c136b0e592e7380f212f54482af0dca88a3647430709f9e554b9c483d7d7db33</cites><orcidid>0000-0002-3607-578X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29356246$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Shengyang</creatorcontrib><creatorcontrib>Sun, Jiansong</creatorcontrib><creatorcontrib>Zhang, Qingju</creatorcontrib><creatorcontrib>Cao, Xin</creatorcontrib><creatorcontrib>Zhao, Yachen</creatorcontrib><creatorcontrib>Tang, Gongli</creatorcontrib><creatorcontrib>Yu, Biao</creatorcontrib><title>Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>The proposed diastereoisomers (1 a–d) together with their C8′‐epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio‐ and stereocontrolled gold(I)‐catalyzed N‐glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.
All in the configuration: The proposed diastereoisomers and the relevant C8′ epimers of amipurimycin, a unique peptidyl nucleoside antibiotic, have been synthesized for the first time. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be in fact of opposite configuration.</description><subject>Aldehydes</subject><subject>Amino acids</subject><subject>Antibiotics</subject><subject>Configurations</subject><subject>Diastereoisomers</subject><subject>Fungicides</subject><subject>Glycosylation</subject><subject>Gold</subject><subject>natural products</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Nucleosides</subject><subject>Sugar</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkE1Lw0AQhhdRbK1ePUrAi5fU_Ux2vZVatVA_oPW8bJMJbkmydTdB-u9Naa3gReYw7-GZl-FB6JLgIcGY3prawpBiIjEmiTpCfSIoiVmasuMuc8biVArSQ2chrDpeSpycoh5VTCSUJ330PKrsuvW22mS2vosWrjFlNN_UzQcEGyJXRF2K3rxbuwB5NG98mzWthxCZOo_urQkNeHA2uAp8OEcnhSkDXOz3AL0_TBbjp3j2-jgdj2ZxxtNExSQjLFliEIpCyiQuKKGF4FxSU-A8M1IalvCUM5xiVSgQgi9VxiXL026WjA3Qza537d1nC6HRlQ0ZlKWpwbVBEyWVIozxLXr9B1251tfdd5pirIjAQm2p4Y7KvAvBQ6HXnRPjN5pgvRWtt6L1QXR3cLWvbZcV5Af8x2wHqB3wZUvY_FOnRy_TyW_5N7pHiPA</recordid><startdate>20180305</startdate><enddate>20180305</enddate><creator>Wang, Shengyang</creator><creator>Sun, Jiansong</creator><creator>Zhang, Qingju</creator><creator>Cao, Xin</creator><creator>Zhao, Yachen</creator><creator>Tang, Gongli</creator><creator>Yu, Biao</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3607-578X</orcidid></search><sort><creationdate>20180305</creationdate><title>Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers</title><author>Wang, Shengyang ; Sun, Jiansong ; Zhang, Qingju ; Cao, Xin ; Zhao, Yachen ; Tang, Gongli ; Yu, Biao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4769-1c136b0e592e7380f212f54482af0dca88a3647430709f9e554b9c483d7d7db33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aldehydes</topic><topic>Amino acids</topic><topic>Antibiotics</topic><topic>Configurations</topic><topic>Diastereoisomers</topic><topic>Fungicides</topic><topic>Glycosylation</topic><topic>Gold</topic><topic>natural products</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Nucleosides</topic><topic>Sugar</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Shengyang</creatorcontrib><creatorcontrib>Sun, Jiansong</creatorcontrib><creatorcontrib>Zhang, Qingju</creatorcontrib><creatorcontrib>Cao, Xin</creatorcontrib><creatorcontrib>Zhao, Yachen</creatorcontrib><creatorcontrib>Tang, Gongli</creatorcontrib><creatorcontrib>Yu, Biao</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Shengyang</au><au>Sun, Jiansong</au><au>Zhang, Qingju</au><au>Cao, Xin</au><au>Zhao, Yachen</au><au>Tang, Gongli</au><au>Yu, Biao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2018-03-05</date><risdate>2018</risdate><volume>57</volume><issue>11</issue><spage>2884</spage><epage>2888</epage><pages>2884-2888</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The proposed diastereoisomers (1 a–d) together with their C8′‐epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio‐ and stereocontrolled gold(I)‐catalyzed N‐glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.
All in the configuration: The proposed diastereoisomers and the relevant C8′ epimers of amipurimycin, a unique peptidyl nucleoside antibiotic, have been synthesized for the first time. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be in fact of opposite configuration.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29356246</pmid><doi>10.1002/anie.201800169</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-3607-578X</orcidid></addata></record> |
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| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2018-03, Vol.57 (11), p.2884-2888 |
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| language | eng |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Aldehydes Amino acids Antibiotics Configurations Diastereoisomers Fungicides Glycosylation Gold natural products NMR Nuclear magnetic resonance Nucleosides Sugar |
| title | Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers |
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