Determining the absolute configuration of vanitaracin A, an anti-hepatitis B virus agent
Vanitaracin A is an anti-hepatitis B virus (anti-HBV) compound isolated from the culture broth of the fungus Talaromyces sp. Vanitaracin A inhibits the entry of HBV into target cells with sub-micromolar IC 50 values. While a structure–activity relationship study is highly desirable, a synthetic appr...
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| Veröffentlicht in: | Journal of antibiotics 2022-02, Vol.75 (2), p.92-97 |
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| container_end_page | 97 |
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| container_issue | 2 |
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| container_title | Journal of antibiotics |
| container_volume | 75 |
| creator | Kamisuki, Shinji Shibasaki, Hisanobu Ashikawa, Koudai Kanno, Kazuki Watashi, Koichi Sugawara, Fumio Kuramochi, Kouji |
| description | Vanitaracin A is an anti-hepatitis B virus (anti-HBV) compound isolated from the culture broth of the fungus
Talaromyces
sp. Vanitaracin A inhibits the entry of HBV into target cells with sub-micromolar IC
50
values. While a structure–activity relationship study is highly desirable, a synthetic approach still needs to be developed, which is difficult because the absolute configurations of the six stereogenic centers in the structure of vanitaracin A have not yet been determined. In the present study, we used the crystalline sponge method to clarify the configuration of the compound after determining the absolute configuration of the secondary alcohol using a modified Mosher ester method. Combining these analyses with the NOESY spectrum of vanitaracin A and NMR analyses of the crude side-chain carboxylic acid obtained by the alkaline hydrolysis of vanitaracin A revealed the absolute configurations of all stereogenic centers in this important compound. |
| doi_str_mv | 10.1038/s41429-021-00496-1 |
| format | Article |
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Talaromyces
sp. Vanitaracin A inhibits the entry of HBV into target cells with sub-micromolar IC
50
values. While a structure–activity relationship study is highly desirable, a synthetic approach still needs to be developed, which is difficult because the absolute configurations of the six stereogenic centers in the structure of vanitaracin A have not yet been determined. In the present study, we used the crystalline sponge method to clarify the configuration of the compound after determining the absolute configuration of the secondary alcohol using a modified Mosher ester method. Combining these analyses with the NOESY spectrum of vanitaracin A and NMR analyses of the crude side-chain carboxylic acid obtained by the alkaline hydrolysis of vanitaracin A revealed the absolute configurations of all stereogenic centers in this important compound.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.1038/s41429-021-00496-1</identifier><identifier>PMID: 35034105</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>631/92/349 ; 631/92/613 ; Absolute configuration ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Bacteriology ; Biomedical and Life Sciences ; Bioorganic Chemistry ; Carboxylic acids ; Cell culture ; Configurations ; Hepatitis ; Hepatitis B ; Hepatitis B virus - drug effects ; Hydrolysis ; Life Sciences ; Magnetic Resonance Spectroscopy ; Medicinal Chemistry ; Microbiology ; Molecular Conformation ; Molecular Structure ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Polyketides - chemistry ; Polyketides - pharmacology ; Structure-Activity Relationship ; Talaromyces - chemistry</subject><ispartof>Journal of antibiotics, 2022-02, Vol.75 (2), p.92-97</ispartof><rights>The Author(s), under exclusive licence to the Japan Antibiotics Research Association 2021</rights><rights>2021. The Author(s), under exclusive licence to the Japan Antibiotics Research Association.</rights><rights>The Author(s), under exclusive licence to the Japan Antibiotics Research Association 2021.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c509t-8e9128eb7eb81571b63ef86944fa5ae447fbda8e74686d768da7e1ddea54f36a3</citedby><cites>FETCH-LOGICAL-c509t-8e9128eb7eb81571b63ef86944fa5ae447fbda8e74686d768da7e1ddea54f36a3</cites><orcidid>0000-0001-8773-3909</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35034105$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kamisuki, Shinji</creatorcontrib><creatorcontrib>Shibasaki, Hisanobu</creatorcontrib><creatorcontrib>Ashikawa, Koudai</creatorcontrib><creatorcontrib>Kanno, Kazuki</creatorcontrib><creatorcontrib>Watashi, Koichi</creatorcontrib><creatorcontrib>Sugawara, Fumio</creatorcontrib><creatorcontrib>Kuramochi, Kouji</creatorcontrib><title>Determining the absolute configuration of vanitaracin A, an anti-hepatitis B virus agent</title><title>Journal of antibiotics</title><addtitle>J Antibiot</addtitle><addtitle>J Antibiot (Tokyo)</addtitle><description>Vanitaracin A is an anti-hepatitis B virus (anti-HBV) compound isolated from the culture broth of the fungus
Talaromyces
sp. Vanitaracin A inhibits the entry of HBV into target cells with sub-micromolar IC
50
values. While a structure–activity relationship study is highly desirable, a synthetic approach still needs to be developed, which is difficult because the absolute configurations of the six stereogenic centers in the structure of vanitaracin A have not yet been determined. In the present study, we used the crystalline sponge method to clarify the configuration of the compound after determining the absolute configuration of the secondary alcohol using a modified Mosher ester method. Combining these analyses with the NOESY spectrum of vanitaracin A and NMR analyses of the crude side-chain carboxylic acid obtained by the alkaline hydrolysis of vanitaracin A revealed the absolute configurations of all stereogenic centers in this important compound.</description><subject>631/92/349</subject><subject>631/92/613</subject><subject>Absolute configuration</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Bacteriology</subject><subject>Biomedical and Life Sciences</subject><subject>Bioorganic Chemistry</subject><subject>Carboxylic acids</subject><subject>Cell culture</subject><subject>Configurations</subject><subject>Hepatitis</subject><subject>Hepatitis B</subject><subject>Hepatitis B virus - drug effects</subject><subject>Hydrolysis</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medicinal Chemistry</subject><subject>Microbiology</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Polyketides - chemistry</subject><subject>Polyketides - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Talaromyces - chemistry</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNp9kE1LAzEQhoMoWj_-gAcJePHgar42yR79VhC8KHgL2d3ZNtJma5It-O9NbVXwIAzMYZ55Z3gQOqTkjBKuz6OgglUFYbQgRFSyoBtoRLWmBRWy2kQjshxpzcgO2o3xjRCuuNLbaIeXhAtKyhF6vYYEYea882OcJoBtHfvpkAA3ve_ceAg2ud7jvsML612ywTbO44tTbH2u5IoJzDOSXMSXeOHCELEdg0_7aKuz0wgH676HXm5vnq_ui8enu4eri8eiKUmVCg0VZRpqBbWmpaK15NBpWQnR2dKCEKqrW6tBCallq6RurQLatmBL0XFp-R46WeXOQ_8-QExm5mID06n10A_RMMmIkhVhPKPHf9C3fgg-f7ekGNe0YmWm2IpqQh9jgM7Mg5vZ8GEoMUvvZuXdZLnmy7uheeloHT3UM2h_Vr5FZ4CvgJhHfgzh9_Y_sZ-jT42Y</recordid><startdate>20220201</startdate><enddate>20220201</enddate><creator>Kamisuki, Shinji</creator><creator>Shibasaki, Hisanobu</creator><creator>Ashikawa, Koudai</creator><creator>Kanno, Kazuki</creator><creator>Watashi, Koichi</creator><creator>Sugawara, Fumio</creator><creator>Kuramochi, Kouji</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</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>3V.</scope><scope>7QL</scope><scope>7T5</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M2P</scope><scope>M7P</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>Q9U</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8773-3909</orcidid></search><sort><creationdate>20220201</creationdate><title>Determining the absolute configuration of vanitaracin A, an anti-hepatitis B virus agent</title><author>Kamisuki, Shinji ; Shibasaki, Hisanobu ; Ashikawa, Koudai ; Kanno, Kazuki ; Watashi, Koichi ; Sugawara, Fumio ; Kuramochi, Kouji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c509t-8e9128eb7eb81571b63ef86944fa5ae447fbda8e74686d768da7e1ddea54f36a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>631/92/349</topic><topic>631/92/613</topic><topic>Absolute configuration</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Bacteriology</topic><topic>Biomedical and Life Sciences</topic><topic>Bioorganic Chemistry</topic><topic>Carboxylic acids</topic><topic>Cell culture</topic><topic>Configurations</topic><topic>Hepatitis</topic><topic>Hepatitis B</topic><topic>Hepatitis B virus - drug effects</topic><topic>Hydrolysis</topic><topic>Life Sciences</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medicinal Chemistry</topic><topic>Microbiology</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Polyketides - chemistry</topic><topic>Polyketides - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Talaromyces - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kamisuki, Shinji</creatorcontrib><creatorcontrib>Shibasaki, Hisanobu</creatorcontrib><creatorcontrib>Ashikawa, Koudai</creatorcontrib><creatorcontrib>Kanno, Kazuki</creatorcontrib><creatorcontrib>Watashi, Koichi</creatorcontrib><creatorcontrib>Sugawara, Fumio</creatorcontrib><creatorcontrib>Kuramochi, Kouji</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Immunology Abstracts</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>Natural Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Science Database</collection><collection>Biological Science Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kamisuki, Shinji</au><au>Shibasaki, Hisanobu</au><au>Ashikawa, Koudai</au><au>Kanno, Kazuki</au><au>Watashi, Koichi</au><au>Sugawara, Fumio</au><au>Kuramochi, Kouji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Determining the absolute configuration of vanitaracin A, an anti-hepatitis B virus agent</atitle><jtitle>Journal of antibiotics</jtitle><stitle>J Antibiot</stitle><addtitle>J Antibiot (Tokyo)</addtitle><date>2022-02-01</date><risdate>2022</risdate><volume>75</volume><issue>2</issue><spage>92</spage><epage>97</epage><pages>92-97</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><abstract>Vanitaracin A is an anti-hepatitis B virus (anti-HBV) compound isolated from the culture broth of the fungus
Talaromyces
sp. Vanitaracin A inhibits the entry of HBV into target cells with sub-micromolar IC
50
values. While a structure–activity relationship study is highly desirable, a synthetic approach still needs to be developed, which is difficult because the absolute configurations of the six stereogenic centers in the structure of vanitaracin A have not yet been determined. In the present study, we used the crystalline sponge method to clarify the configuration of the compound after determining the absolute configuration of the secondary alcohol using a modified Mosher ester method. Combining these analyses with the NOESY spectrum of vanitaracin A and NMR analyses of the crude side-chain carboxylic acid obtained by the alkaline hydrolysis of vanitaracin A revealed the absolute configurations of all stereogenic centers in this important compound.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>35034105</pmid><doi>10.1038/s41429-021-00496-1</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-8773-3909</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | Journal of antibiotics, 2022-02, Vol.75 (2), p.92-97 |
| issn | 0021-8820 1881-1469 |
| language | eng |
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| source | MEDLINE; Alma/SFX Local Collection |
| subjects | 631/92/349 631/92/613 Absolute configuration Antiviral Agents - chemistry Antiviral Agents - pharmacology Bacteriology Biomedical and Life Sciences Bioorganic Chemistry Carboxylic acids Cell culture Configurations Hepatitis Hepatitis B Hepatitis B virus - drug effects Hydrolysis Life Sciences Magnetic Resonance Spectroscopy Medicinal Chemistry Microbiology Molecular Conformation Molecular Structure NMR Nuclear magnetic resonance Organic Chemistry Polyketides - chemistry Polyketides - pharmacology Structure-Activity Relationship Talaromyces - chemistry |
| title | Determining the absolute configuration of vanitaracin A, an anti-hepatitis B virus agent |
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