Author:
Beier Andy,Hahn Veronika,Bornscheuer Uwe T,Schauer Frieder
Abstract
Abstract
Knowledge is scarce about the degradation of ketones in yeasts. For bacteria a subterminal degradation of alkanes to ketones and their further metabolization has been described which always involved Baeyer-Villiger monooxygenases (BVMOs). In addition, the question has to be clarified whether alkenes are converted to ketones, in particular for the oil degrading yeast Candida maltosa little is known. In this study we show the degradation of the aliphatic ketone dodecane-2-one by Candida maltosa and the related yeasts Candida tropicalis, Candida catenulata and Candida albicans as well as Trichosporon asahii and Yarrowia lipolytica. One pathway is initiated by the formation of decyl acetate, resulting from a Baeyer-Villiger-oxidation of this ketone. Beyond this, an initial reduction to dodecane-2-ol by a keto reductase was clearly shown. In addition, two different ways to metabolize dodec-1-ene were proposed. One involved the formation of dodecane-2-one and the other one a conversion leading to carboxylic and dicarboxylic acids. Furthermore the induction of ketone degrading enzymes by dodecane-2-one and dodec-1-ene was shown. Interestingly, with dodecane no subterminal degradation products were detected and it did not induce any enzymes to convert dodecane-2-one.
Publisher
Springer Science and Business Media LLC
Subject
Applied Microbiology and Biotechnology,Biophysics
Reference51 articles.
1. Abeles FB, Morgan PW, Saltveit ME Jr: Ethylene in Plant Biology. Academic press, San Diego; 1992.
2. Alphand V, Archelas A, Furstoss R: Microbial transformations 16. One-step synthesis of a pivotal prostaglandin chiral synthon via a highly enantioselective microbiological Baeyer-Villiger type reaction. Tetrahedron Lett 1989, 30(28):3663–3664. 10.1016/S0040-4039(01)80476-7
3. Balke K, Kadow M, Mallin H, Saß S, Bornscheuer UT: Discovery, application and protein engineering of Baeyer-Villiger monooxygenases for organic synthesis. Org Biomol Chem 2012, 10(31):6249–6265. 10.1039/c2ob25704a
4. Blasig R, Mauersberger S, Riege P, Schunck W-H, Jockisch W, Franke P, Müller H-G: Degradation of long-chain n -alkanes by the yeast Candida maltosa . Appl Microbiol Biotechnol 1988, 28(6):589–597.
5. Bruyn J: An intermediate product in the oxidation of hexadecene-1 by Candida lipolytica . Koninkl Ned Acad Wetenschap Proc Ser C 1954, 57: 41–44.
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