{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T20:14:53Z","timestamp":1760645693814},"reference-count":0,"publisher":"Canadian Science Publishing","issue":"7","license":[{"start":{"date-parts":[[1977,7,1]],"date-time":"1977-07-01T00:00:00Z","timestamp":236563200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/www.nrcresearchpress.com\/page\/about\/CorporateTextAndDataMining"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Can. J. Biochem."],"published-print":{"date-parts":[[1977,7,1]]},"abstract":"<jats:p> The biogenetic origin of the carbon atoms in tenellin has been established by adding <jats:sup>13<\/jats:sup>C-enriched compounds to cultures of Beauveria bassiana, and determining the isotopic distribution in the metabolite by <jats:sup>13<\/jats:sup>C nuclear magnetic resonance spectrometry. Tenellin is formed by condensation of an acetate-derived polyketide chain with a phenylpropanoid unit that may be phenylalanine. Alternate carbon atoms of the polyketide chain were labelled with sodium [1-<jats:sup>13<\/jats:sup>C]- and [2-<jats:sup>13<\/jats:sup>C]-acetate; sodium [1,2-<jats:sup>13<\/jats:sup>C]acetate was incorporated as intact two-carbon units, the presence of which in tenellin was apparent from coupling between adjacent <jats:sup>13<\/jats:sup>C-enriched carbons. Substituent methyl groups of the polyketide-derived alkenyl chain were labelled with L-[Me-<jats:sup>13<\/jats:sup>C]methionine. The labelling patterns from DL-[carboxy-<jats:sup>13<\/jats:sup>C]phenylalanine and DL-[\u03b1-<jats:sup>13<\/jats:sup>C]phenylalanine indicated a rearrangement of the propanoid component at some stage in the synthesis. The mass spectrum of tenellin from cultures administered L-[<jats:sup>15<\/jats:sup>N]phenylalanine showed isotopic enrichment similar to that obtained with <jats:sup>13<\/jats:sup>C- or <jats:sup>14<\/jats:sup>C-labelled phenylalanine. During incorporation of L-[carboxy-<jats:sup>14<\/jats:sup>C, \u03b2-<jats:sup>3<\/jats:sup>H]phenylalanine 96% of the tritium label was lost, discounting the possibility of a 1,2-hydride shift during biosynthesis of the metabolite. <\/jats:p>","DOI":"10.1139\/o77-098","type":"journal-article","created":{"date-parts":[[2009,12,21]],"date-time":"2009-12-21T14:47:54Z","timestamp":1261406874000},"page":"678-685","source":"Crossref","is-referenced-by-count":22,"title":["Use of <sup>13<\/sup>C in biosynthetic studies. The labelling pattern in tenellin enriched from isotope-labelled acetate, methionine, and phenylalanine"],"prefix":"10.1139","volume":"55","author":[{"given":"J. L. C.","family":"Wright","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"L. C.","family":"Vining","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"A. G.","family":"McInnes","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"D. G.","family":"Smith","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"J. A.","family":"Walter","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"155","container-title":["Canadian Journal of Biochemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.nrcresearchpress.com\/doi\/pdf\/10.1139\/o77-098","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2020,1,5]],"date-time":"2020-01-05T22:52:00Z","timestamp":1578264720000},"score":1,"resource":{"primary":{"URL":"http:\/\/www.nrcresearchpress.com\/doi\/10.1139\/o77-098"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1977,7,1]]},"references-count":0,"journal-issue":{"issue":"7","published-print":{"date-parts":[[1977,7,1]]}},"alternative-id":["10.1139\/o77-098"],"URL":"https:\/\/doi.org\/10.1139\/o77-098","relation":{},"ISSN":["0008-4018"],"issn-type":[{"value":"0008-4018","type":"print"}],"subject":[],"published":{"date-parts":[[1977,7,1]]}}}