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Applied and Environmental Microbiology, October 1998, p. 3878-3881, Vol. 64, No. 10
0099-2240/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.

Stereo- and Regioselective Hydroxylation of alpha -Ionone by Streptomyces Strains

Sabine Lutz-Wahl,1 Peter Fischer,2 Claudia Schmidt-Dannert,1 Wolfgang Wohlleben,3 Bernhard Hauer,4 and Rolf D. Schmid1,*

Institut für Technische Biochemie1 and Institut für Organische Chemie und Isotopenforschung,2 Universität Stuttgart, Stuttgart, and Lehrstuhl für Mikrobiologie/Biotechnologie, Universität Tübingen, Tübingen,3 and BASF AG, Ludwigshafen,4 Germany

Received 16 April 1998/Accepted 14 July 1998

A total of 215 Streptomyces strains were screened for their capacity to regio- and stereoselectively hydroxylate beta - and/or alpha -ionone to the respective 3-hydroxy derivatives. With beta -ionone as the substrate, 15 strains showed little conversion to 4-hydroxy- and none showed conversion to the 3-hydroxy product as desired. Among these 15 Streptomyces strains, S. fradiae Tü 27, S. arenae Tü 495, S. griseus ATCC 13273, S. violaceoniger Tü 38, and S. antibioticus Tü 4 and Tü 46 converted alpha -ionone to 3-hydroxy-alpha -ionone with significantly higher hydroxylation activity compared to that of beta -ionone. Hydroxylation of racemic alpha -ionone [(6R)-(-)/(6S)-(+)] resulted in the exclusive formation of only the two enantiomers (3R,6R)- and (3S,6S)-hydroxy-alpha -ionone. Thus, the enzymatic hydroxylation of alpha -ionone by the Streptomyces strains tested proceeds with both high regio- and stereoselectivity.

* Corresponding author. Mailing address: Institut für Technische Biochemie, Universität Stuttgart, Allmandring 31, D-70569 Stuttgart, Germany. Phone: 49-0711-685-3192. Fax: 49-0711-685-4569. E-mail: rolf.d.schmid{at}rus.uni-stuttgart.de.

Applied and Environmental Microbiology, October 1998, p. 3878-3881, Vol. 64, No. 10
0099-2240/98/$04.00+0
Copyright © 1998, American Society for Microbiology. All rights reserved.




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