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Herein the oxa gene cluster from the marine-derived fungus Penicillium oxalicum F30 is described along with the characterization of OxaD, a flavin-dependent oxidase that generates roquefortine L, a nitrone-bearing intermediate in the biosynthesis of oxaline. Nitrone functionality in roquefortine L was confirmed by spectroscopic methods and 1,3-dipolar cycloaddition with methyl acrylate. OxaD is a versatile biocatalyst that converts an array of semisynthetic roquefortine C derivatives bearing indoline systems to their respective nitrones. This work describes the first implementation of a nitrone synthase as a biocatalyst and establishes a novel platform for late-stage diversification of a range of complex natural products.<\/jats:p>","DOI":"10.1021\/jacs.6b04915","type":"journal-article","created":{"date-parts":[[2016,8,9]],"date-time":"2016-08-09T13:32:39Z","timestamp":1470749559000},"page":"11176-11184","source":"Crossref","is-referenced-by-count":51,"title":["OxaD:\nA Versatile Indolic Nitrone Synthase from the\nMarine-Derived Fungus\n                    <i>Penicillium oxalicum<\/i>\n                    F30"],"prefix":"10.1021","volume":"138","author":[{"given":"Sean A.","family":"Newmister","sequence":"first","affiliation":[{"name":"University of Michigan , , Ann Arbor , Michigan 48109 ,","place":["United\nStates"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claire\nM.","family":"Gober","sequence":"additional","affiliation":[{"name":"University of Pennsylvania , , 231 South 34th Street , Philadelphia , Pennsylvania 19104 ,","place":["United States"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stelamar","family":"Romminger","sequence":"additional","affiliation":[{"name":"University of Michigan , , Ann Arbor , Michigan 48109 ,","place":["United\nStates"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fengan","family":"Yu","sequence":"additional","affiliation":[{"name":"University of Michigan , , Ann Arbor , Michigan 48109 ,","place":["United\nStates"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ashootosh","family":"Tripathi","sequence":"additional","affiliation":[{"name":"University of Michigan , , Ann Arbor , Michigan 48109 ,","place":["United\nStates"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lizbeth Lorena\nL.","family":"Parra","sequence":"additional","affiliation":[{"name":"Universidade de Sa\u0303o Paulo , , CP 780 , Sa\u0303o Carlos , Sa\u0303o Paulo CEP 13560-970 ,","place":["Brazil"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert M.","family":"Williams","sequence":"additional","affiliation":[{"name":"Colorado State University , , Fort Collins , Colorado 80523 ,","place":["United States"]},{"name":"University of Colorado Cancer Center , Aurora , Colorado 80045 ,","place":["United States"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roberto G. 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