Structure of the antibiotic OA-7653
The structure of the glycopeptide antibiotic OA-7653 is assigned. Elucidation of the structure is based primarily on two-dimensional NMR experiments, analogies with other glycopeptide antibiotics of the vancomycin series, and selective degradation studies. Antibiotic OA-7653 contains a heptapeptide...
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| Veröffentlicht in: | Journal of organic chemistry 1988-02, Vol.53 (3), p.471-477 |
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| container_end_page | 477 |
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| container_issue | 3 |
| container_start_page | 471 |
| container_title | Journal of organic chemistry |
| container_volume | 53 |
| creator | Jeffs, Peter W Yellin, Benjamin Mueller, Luciano Heald, Sarah L |
| description | The structure of the glycopeptide antibiotic OA-7653 is assigned. Elucidation of the structure is based primarily on two-dimensional NMR experiments, analogies with other glycopeptide antibiotics of the vancomycin series, and selective degradation studies. Antibiotic OA-7653 contains a heptapeptide aglycon core in which the amino acids N,N-dimethylalanine and glutamine are encountered as the G and F components of this unit. Mild acid hydrolysis of the antibiotic effects the conversion of the gamma -carboxamide of the glutamine residue to yield the carboxylic acid 3 in a reaction that is shown to proceed without rearrangement. This latter conversion to 3 proceeds without effecting cleavage of the beta -glycosidic link between the aglycon and glucose. The super(1)H spectra of OA-7653 and its derivatives in DMSO at pH 4.0 are shown to represent major and minor conformers that are exchanging at rates comparable to the NMR time scale. |
| doi_str_mv | 10.1021/jo00238a002 |
| format | Article |
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Elucidation of the structure is based primarily on two-dimensional NMR experiments, analogies with other glycopeptide antibiotics of the vancomycin series, and selective degradation studies. Antibiotic OA-7653 contains a heptapeptide aglycon core in which the amino acids N,N-dimethylalanine and glutamine are encountered as the G and F components of this unit. Mild acid hydrolysis of the antibiotic effects the conversion of the gamma -carboxamide of the glutamine residue to yield the carboxylic acid 3 in a reaction that is shown to proceed without rearrangement. This latter conversion to 3 proceeds without effecting cleavage of the beta -glycosidic link between the aglycon and glucose. The super(1)H spectra of OA-7653 and its derivatives in DMSO at pH 4.0 are shown to represent major and minor conformers that are exchanging at rates comparable to the NMR time scale.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo00238a002</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Atomic and molecular physics ; Exact sciences and technology ; General molecular conformation and symmetry; stereochemistry ; Molecular properties and interactions with photons ; Physics ; Properties of molecules and molecular ions</subject><ispartof>Journal of organic chemistry, 1988-02, Vol.53 (3), p.471-477</ispartof><rights>1989 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a361t-ee3ec7235b8230fa6b74429cc6adcea10e1515149723f44bb97f870e5860de3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo00238a002$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo00238a002$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7126233$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Jeffs, Peter W</creatorcontrib><creatorcontrib>Yellin, Benjamin</creatorcontrib><creatorcontrib>Mueller, Luciano</creatorcontrib><creatorcontrib>Heald, Sarah L</creatorcontrib><title>Structure of the antibiotic OA-7653</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The structure of the glycopeptide antibiotic OA-7653 is assigned. Elucidation of the structure is based primarily on two-dimensional NMR experiments, analogies with other glycopeptide antibiotics of the vancomycin series, and selective degradation studies. Antibiotic OA-7653 contains a heptapeptide aglycon core in which the amino acids N,N-dimethylalanine and glutamine are encountered as the G and F components of this unit. Mild acid hydrolysis of the antibiotic effects the conversion of the gamma -carboxamide of the glutamine residue to yield the carboxylic acid 3 in a reaction that is shown to proceed without rearrangement. This latter conversion to 3 proceeds without effecting cleavage of the beta -glycosidic link between the aglycon and glucose. The super(1)H spectra of OA-7653 and its derivatives in DMSO at pH 4.0 are shown to represent major and minor conformers that are exchanging at rates comparable to the NMR time scale.</description><subject>Atomic and molecular physics</subject><subject>Exact sciences and technology</subject><subject>General molecular conformation and symmetry; stereochemistry</subject><subject>Molecular properties and interactions with photons</subject><subject>Physics</subject><subject>Properties of molecules and molecular ions</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNptkEtLAzEQx4MoWKsnv8CCogdZzWOT7B6lWh8Uq7Sgt5BNZzF1u1uTLOi3N7KleHAGZmDmNw_-CB0TfEkwJVfLFmPKch3jDhoQTnEqCpztokGs0JRRwfbRgfdLHI1zPkAns-A6EzoHSVsl4R0S3QRb2jZYk0yvUyk4O0R7la49HG3yEM3Gt_PRfTqZ3j2MriepZoKEFICBkZTxMqcMV1qUMstoYYzQCwOaYCA8elZEpsqysixklUsMPBd4AWyIzvqta9d-duCDWllvoK51A23nFeEZkYLRCF70oHGt9w4qtXZ2pd23Ilj9yqD-yBDp081a7Y2uK6cbY_12RBIqKGMRS3vM-gBf27Z2H0pIJrmaP8_U0_jmLX98weo18uc9r42P9zrXRGX-feAHZKZ0_Q</recordid><startdate>19880201</startdate><enddate>19880201</enddate><creator>Jeffs, Peter W</creator><creator>Yellin, Benjamin</creator><creator>Mueller, Luciano</creator><creator>Heald, Sarah L</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>19880201</creationdate><title>Structure of the antibiotic OA-7653</title><author>Jeffs, Peter W ; Yellin, Benjamin ; Mueller, Luciano ; Heald, Sarah L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a361t-ee3ec7235b8230fa6b74429cc6adcea10e1515149723f44bb97f870e5860de3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Atomic and molecular physics</topic><topic>Exact sciences and technology</topic><topic>General molecular conformation and symmetry; stereochemistry</topic><topic>Molecular properties and interactions with photons</topic><topic>Physics</topic><topic>Properties of molecules and molecular ions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jeffs, Peter W</creatorcontrib><creatorcontrib>Yellin, Benjamin</creatorcontrib><creatorcontrib>Mueller, Luciano</creatorcontrib><creatorcontrib>Heald, Sarah L</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jeffs, Peter W</au><au>Yellin, Benjamin</au><au>Mueller, Luciano</au><au>Heald, Sarah L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure of the antibiotic OA-7653</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>1988-02-01</date><risdate>1988</risdate><volume>53</volume><issue>3</issue><spage>471</spage><epage>477</epage><pages>471-477</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The structure of the glycopeptide antibiotic OA-7653 is assigned. Elucidation of the structure is based primarily on two-dimensional NMR experiments, analogies with other glycopeptide antibiotics of the vancomycin series, and selective degradation studies. Antibiotic OA-7653 contains a heptapeptide aglycon core in which the amino acids N,N-dimethylalanine and glutamine are encountered as the G and F components of this unit. Mild acid hydrolysis of the antibiotic effects the conversion of the gamma -carboxamide of the glutamine residue to yield the carboxylic acid 3 in a reaction that is shown to proceed without rearrangement. This latter conversion to 3 proceeds without effecting cleavage of the beta -glycosidic link between the aglycon and glucose. 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| ispartof | Journal of organic chemistry, 1988-02, Vol.53 (3), p.471-477 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_15417632 |
| source | ACS Publications |
| subjects | Atomic and molecular physics Exact sciences and technology General molecular conformation and symmetry stereochemistry Molecular properties and interactions with photons Physics Properties of molecules and molecular ions |
| title | Structure of the antibiotic OA-7653 |
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