Enzymatic formation of indole-containing unnatural cyclic polyprenoids by bacterial squalene:hopene cyclase |
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Authors: | Tanaka Hideya Noguchi Hiroshi Abe Ikuro |
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Affiliation: | School of Pharmaceutical Sciences and the COE 21 Program, University of Shizuoka, Shizuoka 422-8526, Japan. |
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Abstract: | [reaction: see text] Two indole-containing substrate analogues, in which a C20 isoprene unit is connected to indole (3-(geranylgeranyl)indole and 3-(farnesyldimethylallyl)indole), were synthesized and tested for enzymatic cyclization by squalene:hopene cyclase from Alicyclobacillus acidocaldarius. Interestingly, 3-(geranylgeranyl)indole was not a substrate for the bacterial squalene cyclase, while 3-(farnesyldimethylallyl)indole was efficiently converted to a 2:1 mixture of unnatural novel products. |
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