PROOF FOR THE BIOSYNTHETIC CONVERSION OF L-[INDOLE-15N]TRYPTOPHAN TO [10-15N]ANTHRAMYCIN USING (13C, 15N) LABELLING IN CONJUNCTION WITH 13C-NMR AND MASS SPECTRAL ANALYSIS
Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 15N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived f...
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| Veröffentlicht in: | Journal of antibiotics 1980, Vol.33(10), pp.1167-1171 |
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| container_issue | 10 |
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| container_title | Journal of antibiotics |
| container_volume | 33 |
| creator | OSTRANDER, JOHN M. HURLEY, LAURENCE H. MCINNES, A. GAVIN SMITH, DONALD G. WALTER, JOHN A. WRIGHT, JEFFREY L. C. |
| description | Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 15N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[1-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-15N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 15N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin. |
| doi_str_mv | 10.7164/antibiotics.33.1167 |
| format | Article |
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GAVIN ; SMITH, DONALD G. ; WALTER, JOHN A. ; WRIGHT, JEFFREY L. C.</creator><creatorcontrib>OSTRANDER, JOHN M. ; HURLEY, LAURENCE H. ; MCINNES, A. GAVIN ; SMITH, DONALD G. ; WALTER, JOHN A. ; WRIGHT, JEFFREY L. C.</creatorcontrib><description>Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 15N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[1-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-15N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 15N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.7164/antibiotics.33.1167</identifier><identifier>PMID: 7451368</identifier><language>eng</language><publisher>Japan: JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</publisher><subject>Amino Acids - metabolism ; Anthramycin - biosynthesis ; Benzodiazepinones - biosynthesis ; Biotransformation ; Fermentation ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Nitrogen Isotopes ; Tryptophan - metabolism</subject><ispartof>The Journal of Antibiotics, 1980, Vol.33(10), pp.1167-1171</ispartof><rights>Japan Antibiotics Research Association</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3297-20ef56affdd4fc8bef4fd4dc9a84c2cb7c1ca78174ea400f8c4ad97d4ef092853</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7451368$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>OSTRANDER, JOHN M.</creatorcontrib><creatorcontrib>HURLEY, LAURENCE H.</creatorcontrib><creatorcontrib>MCINNES, A. GAVIN</creatorcontrib><creatorcontrib>SMITH, DONALD G.</creatorcontrib><creatorcontrib>WALTER, JOHN A.</creatorcontrib><creatorcontrib>WRIGHT, JEFFREY L. C.</creatorcontrib><title>PROOF FOR THE BIOSYNTHETIC CONVERSION OF L-[INDOLE-15N]TRYPTOPHAN TO [10-15N]ANTHRAMYCIN USING (13C, 15N) LABELLING IN CONJUNCTION WITH 13C-NMR AND MASS SPECTRAL ANALYSIS</title><title>Journal of antibiotics</title><addtitle>J. Antibiot.</addtitle><description>Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 15N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[1-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-15N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 15N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.</description><subject>Amino Acids - metabolism</subject><subject>Anthramycin - biosynthesis</subject><subject>Benzodiazepinones - biosynthesis</subject><subject>Biotransformation</subject><subject>Fermentation</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Nitrogen Isotopes</subject><subject>Tryptophan - metabolism</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1980</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkdtu0zAAhi0EGmXwBAjJVwgkUuzYjZ3LLEvXoNSukhRUTShyHRsy9TDi9oJX4ilx1qrajW39h88XPwDvMRozHNGvanfo1t3-0Gk3JmSMccRegBHmHAeYRvFLMEIoxAHnIXoN3jj3gBBhhPErcMXoBJOIj8C_RSnlFE5lCetZBm9yWa2Ef9V5ClMpvmdllUsBfaQI7nNxK4sswBPxsy5Xi1ouZomAtYT3GD2pia-WyXyV5gIuq1zcwU-YpF-g9z7DIrnJimIQvevZ35YirQf4j7yeQZ8LxLyEibiF86SqYLXI0rpMCq8kxarKq7fglVUbZ96d72uwnGZ1OgsKeZenSRFoEsYsCJGxk0hZ27bUar42ltqWtjpWnOpQr5nGWjGOGTWKImS5pqqNWUuNRXHIJ-QafDxxH_v9n6Nxh2bbOW02G7Uz-6Nr2ITEnDPig-QU1P3eud7Y5rHvtqr_22DUDAs1zxZqCGmGhXzrwxl_XG9Ne-mcJ_G-OPkP7qB-mYuveo_ZmOdMHEf8iYvO5_DBJah_q74xO_IfV7efRw</recordid><startdate>1980</startdate><enddate>1980</enddate><creator>OSTRANDER, JOHN M.</creator><creator>HURLEY, LAURENCE H.</creator><creator>MCINNES, A. GAVIN</creator><creator>SMITH, DONALD G.</creator><creator>WALTER, JOHN A.</creator><creator>WRIGHT, JEFFREY L. C.</creator><general>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</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>7X8</scope></search><sort><creationdate>1980</creationdate><title>PROOF FOR THE BIOSYNTHETIC CONVERSION OF L-[INDOLE-15N]TRYPTOPHAN TO [10-15N]ANTHRAMYCIN USING (13C, 15N) LABELLING IN CONJUNCTION WITH 13C-NMR AND MASS SPECTRAL ANALYSIS</title><author>OSTRANDER, JOHN M. ; HURLEY, LAURENCE H. ; MCINNES, A. GAVIN ; SMITH, DONALD G. ; WALTER, JOHN A. ; WRIGHT, JEFFREY L. C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3297-20ef56affdd4fc8bef4fd4dc9a84c2cb7c1ca78174ea400f8c4ad97d4ef092853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1980</creationdate><topic>Amino Acids - metabolism</topic><topic>Anthramycin - biosynthesis</topic><topic>Benzodiazepinones - biosynthesis</topic><topic>Biotransformation</topic><topic>Fermentation</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Nitrogen Isotopes</topic><topic>Tryptophan - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>OSTRANDER, JOHN M.</creatorcontrib><creatorcontrib>HURLEY, LAURENCE H.</creatorcontrib><creatorcontrib>MCINNES, A. GAVIN</creatorcontrib><creatorcontrib>SMITH, DONALD G.</creatorcontrib><creatorcontrib>WALTER, JOHN A.</creatorcontrib><creatorcontrib>WRIGHT, JEFFREY L. C.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>OSTRANDER, JOHN M.</au><au>HURLEY, LAURENCE H.</au><au>MCINNES, A. GAVIN</au><au>SMITH, DONALD G.</au><au>WALTER, JOHN A.</au><au>WRIGHT, JEFFREY L. C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>PROOF FOR THE BIOSYNTHETIC CONVERSION OF L-[INDOLE-15N]TRYPTOPHAN TO [10-15N]ANTHRAMYCIN USING (13C, 15N) LABELLING IN CONJUNCTION WITH 13C-NMR AND MASS SPECTRAL ANALYSIS</atitle><jtitle>Journal of antibiotics</jtitle><addtitle>J. Antibiot.</addtitle><date>1980</date><risdate>1980</risdate><volume>33</volume><issue>10</issue><spage>1167</spage><epage>1171</epage><pages>1167-1171</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><abstract>Using 13C-NMR and mass spectral analysis we have demonstrated that the N-10 nitrogen of anthramycin is biosynthetically derived from the indole-nitrogen of tryptophan. Our experimental approach was to bring a 15N atom, which is derived from L-[indole-15N]tryptophan, and a 13C atom which is derived from DL-[1-13C]tyrosine, into adjacent positions of anthramycin. From resonance intensities and 13C-15N spin-spin coupling in the 13C-NMR spectrum of didehydroanhydroanthramycin, a derivative of anthramycin, we could then determine the 13C enrichment at C-11 and the proportion of 13C bonded to 15N at N-10. These results when combined with mass spectral analysis and isotopic dilution measurements proved that the indole nitrogen of tryptophan was completely retained at N-10 of anthramycin.</abstract><cop>Japan</cop><pub>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</pub><pmid>7451368</pmid><doi>10.7164/antibiotics.33.1167</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | The Journal of Antibiotics, 1980, Vol.33(10), pp.1167-1171 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_75398873 |
| source | J-STAGE Free; MEDLINE |
| subjects | Amino Acids - metabolism Anthramycin - biosynthesis Benzodiazepinones - biosynthesis Biotransformation Fermentation Magnetic Resonance Spectroscopy Mass Spectrometry Nitrogen Isotopes Tryptophan - metabolism |
| title | PROOF FOR THE BIOSYNTHETIC CONVERSION OF L-[INDOLE-15N]TRYPTOPHAN TO [10-15N]ANTHRAMYCIN USING (13C, 15N) LABELLING IN CONJUNCTION WITH 13C-NMR AND MASS SPECTRAL ANALYSIS |
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