{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,7]],"date-time":"2026-03-07T19:37:37Z","timestamp":1772912257698,"version":"3.50.1"},"reference-count":52,"publisher":"Wiley","issue":"19","license":[{"start":{"date-parts":[[2005,8,12]],"date-time":"2005-08-12T00:00:00Z","timestamp":1123804800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2005,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The volatiles released by two strains of the myxobacterium <jats:italic>Chondromyces crocatus<\/jats:italic> and seven strains of marine Alphaproteobacteria from the North Sea were collected using the CLSA or SPME headspace methods and analysed by GC\u2010MS. In the extracts of <jats:italic>C. crocatus<\/jats:italic> 27 pyrazines were identified, belonging to different classes. 2,5\u2010Dialkylpyrazines and related 3\u2010methoxy\u20102,5\u2010dialkylpyrazines dominated. Several pyrazines like 2\u2010(1\u2010methylethenyl)\u20105\u2010(1\u2010methylethyl)pyrazine (<jats:bold>7<\/jats:bold>) and 3\u2010methoxy\u20102,5\u2010dialkylpyrazines with methyl, isopropyl, isobutyl or <jats:italic>sec<\/jats:italic>\u2010butyl side\u2010chains were obtained from natural sources for the first time. It was essential for the identification to rely on synthetic reference materials, which were obtained using F\u00fcrstner\u2019s iron\u2010catalysed coupling of chloropyrazines with Grignard reagents or condensation of azido ketones as key steps. The synthetic material allowed the identification of two previously unknown attractants of bacterial origin for the pineapple beetle <jats:italic>Carpophilus humeralis<\/jats:italic>, namely 3\u2010methoxy\u20102\u2010(1\u2010methylpropyl)\u20105\u2010(2\u2010methylpropyl)pyrazine (<jats:bold>17<\/jats:bold>) and 3\u2010methoxy\u20102,5\u2010bis(1\u2010methylpropyl)pyrazine (<jats:bold>52<\/jats:bold>). Several 2,5\u2010dialkylpyrazines were identified in the extracts of the marine Alphaproteobacteria. The unique 2,5\u2010dimethyl\u20103\u2010(methylsulfanyl)pyrazine (<jats:bold>67<\/jats:bold>) represents a new type of natural pyrazine. Our results, together with literature reports, show that pyrazines are an important class of bacterial volatiles which might be more widespread than previously thought. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2005)<\/jats:p>","DOI":"10.1002\/ejoc.200500280","type":"journal-article","created":{"date-parts":[[2005,8,12]],"date-time":"2005-08-12T07:46:23Z","timestamp":1123832783000},"page":"4141-4153","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":118,"title":["Novel Pyrazines from the Myxobacterium <i>Chondromyces crocatus<\/i> and Marine Bacteria"],"prefix":"10.1002","volume":"2005","author":[{"given":"Jeroen S.","family":"Dickschat","sequence":"first","affiliation":[]},{"given":"Hans","family":"Reichenbach","sequence":"additional","affiliation":[]},{"given":"Irene","family":"Wagner\u2010D\u00f6bler","sequence":"additional","affiliation":[]},{"given":"Stefan","family":"Schulz","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2005,9,13]]},"reference":[{"key":"e_1_2_6_1_2","volume-title":"Drug Discovery from Nature","author":"Reichenbach H.","year":"1999"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.micro.58.030603.123620"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.95.19.11263"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.95.19.11268"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.33.1474"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.36.1150"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.37.454"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.49.560"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-6968.1981.tb07653.x"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.03.005"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200300813"},{"key":"e_1_2_6_12_2","unstructured":"J. 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