Directed evolution of the dioxygenase complex for the synthesis of furanone flavor compounds

• Published in: Tetrahedron Vol. 60; no. 3; pp. 729 - 734
• Main Authors: Newman, Lisa M., Garcia, Henry, Hudlicky, Tomas, Selifonov, Sergey A.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01-01-2004
• Subjects: Fragaria
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2003.10.105

Herein we report a new preparation of 4-hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one, the flavor compound strawberry furanone, based on a ‘green’ approach with a minimum number of steps. The first step is an enzymatic dioxygenation of
p-xylene to form cyclohexadiene-
cis-diol, followed by ring opening via ozonolysis, and ring closure to form the furanone. In efforts to improve the efficiency of the enzymatic step, a directed evolution approach was taken to increase the substrate specificity and selectivity of the toluene dioxygenase enzyme system.
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