{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,31]],"date-time":"2025-10-31T06:36:44Z","timestamp":1761892604832},"reference-count":21,"publisher":"Proceedings of the National Academy of Sciences","issue":"19","content-domain":{"domain":["www.pnas.org"],"crossmark-restriction":true},"short-container-title":["Proc. Natl. Acad. Sci. U.S.A."],"published-print":{"date-parts":[[1998,9,15]]},"abstract":"<jats:p>\n            Approximately 2 \u03bcmol of a novel prokaryotic pheromone, involved in starvation-induced aggregation and formation of fruiting bodies by the myxobacterium\n            <jats:italic>Stigmatella aurantiaca<\/jats:italic>\n            , were isolated by a large-scale elution procedure. The pheromone was purified by HPLC, and high-resolution MS, IR,\n            <jats:sup>1<\/jats:sup>\n            H-NMR, and\n            <jats:sup>13<\/jats:sup>\n            C-NMR were used to identify the active substance as the hydroxy ketone 2,5,8-trimethyl-8-hydroxy-nonan-4-one, which has been named stigmolone. The analysis was complicated by a solvent-dependent equilibrium between stigmolone and the cyclic enol-ether 3,4-dihydro-2,2,5-trimethyl-6-(2-methylpropyl)-2\n            <jats:italic>H<\/jats:italic>\n            -pyran formed by intramolecular nucleophilic attack of the 8-OH group at the ketone C4 followed by loss of H\n            <jats:sub>2<\/jats:sub>\n            O. Both compounds were synthesized chemically, and their structures were confirmed by NMR analysis. Natural and synthetic stigmolone have the same biological activity at\n            <jats:italic>ca.<\/jats:italic>\n            1 nM concentration.\n          <\/jats:p>","DOI":"10.1073\/pnas.95.19.11268","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T14:40:52Z","timestamp":1027694452000},"page":"11268-11273","update-policy":"http:\/\/dx.doi.org\/10.1073\/pnas.cm10313","source":"Crossref","is-referenced-by-count":28,"title":["Structure elucidation and chemical synthesis of stigmolone, a novel type of prokaryotic pheromone"],"prefix":"10.1073","volume":"95","author":[{"given":"William E.","family":"Hull","sequence":"first","affiliation":[{"name":"Central Spectroscopy Department, German Cancer Research Center, Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany; Institut f\u00fcr Organische Chemie der Universit\u00e4t zu K\u00f6ln, Greinstra\u03b2e 4, D-50939 Cologne, Germany; and Zentrum f\u00fcr Molekulare Biologie der Universit\u00e4t Heidelberg (ZMBH), Im Neuenheimer Feld 282, D-69120 Heidelberg, Germany"}]},{"given":"Albrecht","family":"Berkessel","sequence":"additional","affiliation":[{"name":"Central Spectroscopy Department, German Cancer Research Center, Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany; Institut f\u00fcr Organische Chemie der Universit\u00e4t zu K\u00f6ln, Greinstra\u03b2e 4, D-50939 Cologne, Germany; and Zentrum f\u00fcr Molekulare Biologie der Universit\u00e4t Heidelberg (ZMBH), Im Neuenheimer Feld 282, D-69120 Heidelberg, Germany"}]},{"given":"Wulf","family":"Plaga","sequence":"additional","affiliation":[{"name":"Central Spectroscopy Department, German Cancer Research Center, Im Neuenheimer Feld 280, D-69120 Heidelberg, Germany; Institut f\u00fcr Organische Chemie der Universit\u00e4t zu K\u00f6ln, Greinstra\u03b2e 4, D-50939 Cologne, Germany; and Zentrum f\u00fcr Molekulare Biologie der Universit\u00e4t Heidelberg (ZMBH), Im Neuenheimer Feld 282, D-69120 Heidelberg, Germany"}]}],"member":"341","published-online":{"date-parts":[[1998,9,15]]},"reference":[{"key":"e_1_3_3_1_2","doi-asserted-by":"publisher","DOI":"10.1038\/183055a0"},{"key":"e_1_3_3_2_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.58.3.1152"},{"key":"e_1_3_3_3_2","doi-asserted-by":"publisher","DOI":"10.1515\/bchm2.1961.324.1.84"},{"key":"e_1_3_3_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/0966-842X(96)81525-3"},{"key":"e_1_3_3_5_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.micro.51.1.527"},{"key":"e_1_3_3_6_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-76293-2_9"},{"key":"e_1_3_3_7_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.92.2.641"},{"key":"e_1_3_3_8_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.92.1.37"},{"key":"e_1_3_3_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1074-5521(96)90125-8"},{"key":"e_1_3_3_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/379684a0"},{"key":"e_1_3_3_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/0966-842X(94)90110-Q"},{"key":"e_1_3_3_12_2","doi-asserted-by":"publisher","DOI":"10.1128\/mr.54.4.473-501.1990"},{"key":"e_1_3_3_13_2","doi-asserted-by":"publisher","DOI":"10.1128\/mr.60.1.70-102.1996"},{"key":"e_1_3_3_14_2","doi-asserted-by":"publisher","DOI":"10.1128\/jb.149.2.739-747.1982"},{"key":"e_1_3_3_15_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.95.19.11263"},{"key":"e_1_3_3_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/0012-1606(78)90291-9"},{"key":"e_1_3_3_17_2","first-page":"67","volume-title":"Two-Dimensional NMR Spectroscopy","author":"Hull W E","year":"1994","unstructured":"W E Hull Two-Dimensional NMR Spectroscopy, eds W R Croasmun, R M K Carlson (VCH, 2nd Ed., New York), pp. 67\u2013456 (1994).","edition":"2"},{"key":"e_1_3_3_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)83461-4"},{"key":"e_1_3_3_19_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.60.1925"},{"key":"e_1_3_3_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)86986-6"},{"key":"e_1_3_3_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)96694-3"}],"container-title":["Proceedings of the National Academy of Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pnas.org\/doi\/pdf\/10.1073\/pnas.95.19.11268","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,4,13]],"date-time":"2022-04-13T19:54:28Z","timestamp":1649879668000},"score":1,"resource":{"primary":{"URL":"https:\/\/pnas.org\/doi\/full\/10.1073\/pnas.95.19.11268"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1998,9,15]]},"references-count":21,"journal-issue":{"issue":"19","published-print":{"date-parts":[[1998,9,15]]}},"alternative-id":["10.1073\/pnas.95.19.11268"],"URL":"https:\/\/doi.org\/10.1073\/pnas.95.19.11268","relation":{},"ISSN":["0027-8424","1091-6490"],"issn-type":[{"value":"0027-8424","type":"print"},{"value":"1091-6490","type":"electronic"}],"subject":[],"published":{"date-parts":[[1998,9,15]]},"assertion":[{"value":"1998-05-06","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"1998-09-15","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}