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Ketoisophorone synthesis with an immobilized alcohol dehydrogenase
Solé Ferré, Jordi (Universitat Autònoma de Barcelona. Departament d'Enginyeria Química, Biològica i Ambiental)
Brummund, Jan (InnoSyn B.V.)
Caminal i Saperas, Glòria (Institut de Química Avançada de Catalunya)
Schürman, Martin (InnoSyn B.V.)
Álvaro, Gregorio (Universitat Autònoma de Barcelona. Departament d'Enginyeria Química, Biològica i Ambiental)
Guillén, Marina (Universitat Autònoma de Barcelona. Departament d'Enginyeria Química, Biològica i Ambiental)

Data: 2019
Resum: The monoterpenoid α-isophorone is sourced from the available and renewable plant dry matter, as well as a waste recovery operation from acetone. This compound, can be hydroxylated to 4-hydroxy-isophorone which is the main precursor for the synthesis of ketoisophorone. On its turn, ketoisophorone is a key intermediate for the production of carotenoids and Vitamin E. Here, the enzymatic oxidation of 4-hydroxy-isophorone to ketoisophorone is demonstrated employing an alcohol dehydrogenase (ADHaa) from Artemisia annua and a NADPH oxidase (NOX), as a cofactor regeneration enzyme. After 24 h of reaction and an initial substrate concentration of 50 mM, 95. 7 % yield and a space time yield of 6. 52 g L⁻¹ day⁻¹ could be obtained. Furthermore, the immobilization of the alcohol dehydrogenase was studied on 17 different supports. An epoxy-functionalized agarose resulted in the highest metrics, 100±0% immobilization yield and 58. 2±3. 5 % retained activity. Finally, the immobilized ADHaa was successfully implemented in 4 reaction cycles (96 h operation) presenting a biocatalyst yield of 23. 4 g product g⁻¹ of enzyme. It represents a 2. 5-fold increase compared with the reaction with soluble enzymes.
Ajuts: European Commission 635734
Agència de Gestió d'Ajuts Universitaris i de Recerca 2017/SGR-1462
Nota: Altres ajuts: Authors also thank COST Action CM 1303-Systems Biocatalysis for financial support.
Drets: Tots els drets reservats.
Llengua: Anglès
Document: Article ; recerca ; Versió acceptada per publicar
Matèria: Alcohol dehydrogenase ; Biocatalysis ; Immobilization ; Ketoisophorone ; Recycling
Publicat a: CHEMCACHEM, Vol. 11, issue 19 (Oct. 2019) , p. 4862-4870, ISSN 1867-3880

DOI: 10.1002/cctc.201901090

20 p, 1.1 MB

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