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Converting revere to regular: Reinvestigation of cyclic dipeptide N-prenyltransferase (CdpNPT) revealed that the enzymatic products are derivatives that carry 3′-(3′,3′)-dimethylallyl moieties at the N-1 position of the indole ring, and they undergo rearrangement in the presence of acids, such as trichloroacetic acid, used for termination of enzymatic reactions and protein precipitation (see scheme). The rearrangement can be avoided by using MeOH instead of acid for termination and protein precipitation.
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Ruan et al. (2008) studied this question.
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