Tryptophan prenyltransferases showing higher catalytic activities for Friedel-Crafts alkylation of o- and m-tyrosines than tyrosine prenyltransferases


Tryptophan prenyltransferases FgaPT2, 5-DMATS, 6-DMATSSv and 7-DMATS catalyse regiospecific C-prenylations on the indole ring, while tyrosine prenyltransferases SirD and TyrPT catalyse the O-prenylation of the phenolic hydroxyl group. In this study, we report the Friedel-Crafts alkylation of L-o-tyrosine by these enzymes. Surprisingly, no conversion was detected with SirD and three tryptophan prenyltransferases showed significantly higher activity than another tyrosine prenyltransferase TyrPT. C5-prenylated L-o-tyrosine was identified as a unique product of these enzymes. Using L-m-tyrosine as the prenylation substrate, product formation was only observed with the tryptophan prenyltransferases FgaPT2 and 7-DMATS. C4- and C6-prenylated derivatives were identified in the reaction mixture of FgaPT2. These results provided additional evidence for the similarities and differences between these two subgroups within the DMATS superfamily in their catalytic behaviours.


Aili Fan, Xiulan Xieb, Shu-Ming Li


Organic & Biomolecular Chemistry

Year, Volume, Page

2015, 13, 7551



Tag Element Regiochemistry Product Substrate Cofactor Enzyme
PTDBREC00038 C Regular FgaPT2
PTDBREC00039 O Regular SirD
PTDBREC00040 C Regular FgaPT2
PTDBREC00041 C Regular 5-DMATS
PTDBREC00042 C Regular 6-DMATSSV
PTDBREC00043 C Regular 7-DMATS
PTDBREC00044 C Regular TyrPT
PTDBREC00045 C Regular SirD
PTDBREC00046 C Regular FgaPT2
PTDBREC00047 C Regular FgaPT2
PTDBREC00048 C Regular 5-DMATS
PTDBREC00049 C Regular 6-DMATSSV
PTDBREC00050 C Regular 7-DMATS
PTDBREC00051 C Regular TyrPT
PTDBREC00052 C Regular SirD
PTDBREC00053 C Regular FgaPT2
PTDBREC00054 O Regular 7-DMATS
PTDBREC00055 O Regular TyrPT