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Expansion of Enzymatic Friedel-Crafts Alkylation on Indoles: Acceptance of Unnatural beta-Unsaturated Allyl Diphospates by Dimethylallyl-tryptophan Synthases

  作者 LIEBHOLD MIKE; XIE XIULAN; LI SHUMING  
  选自 期刊  Organic Letters;  卷期  2012年14-18;  页码  4882-4885  
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[摘要]Prenyltransferases of the dimethylallyl-tryptophan synthase (DMATS) superfamily catalyze Friedel-Crafts alkylation with high flexibility for aromatic substrates, but the high specificity for dimethylallyl diphosphate (DMAPP) prohibits their application as biocatalysts. We demonstrate here that at least one methyl group in DMAPP can be deleted or shifted to the delta-position. For acceptance by some DMATS enzymes, however, a double bond must be situated at the beta-position. Furthermore, the alkylation position of an analogue can differ from that of DMAPP.

 
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