期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 7, 期 10, 页码 2202-2207出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b902413a
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资金
- Deutsche Forschungsgemeinschaft [SPP 1152]
In previous studies, two prenyltransferases were overproduced and characterised biochemically. AnaPT from Neosartorya fischeri is involved in the biosynthesis of acetylaszonalenin and was shown to catalyse the C3-prenylation of (R)-benzodiazepinedione (6). CdpNPT from Aspergillus fumigatus catalysed the N1-prenylation of different tryptophan-containing cyclic dipeptides. In this report, CdpNPT was found to catalyse the C3-prenylation of 6 and its (S)-isomer ( 7). Interestingly, AnaPT and CdpNPT introduced prenyl moieties from opposite sides of the indoline ring system. This feature was successfully used for the chemoenzymatic synthesis of four aszonalenin stereoisomers by using 6 and 7 as substrates and AnaPT and CdpNPT as catalysts. The stereoselectivity of the one-step reactions was about 100% and the conversion rates reached 85-100%.
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