Potential of a 7-dimethylallyltryptophan synthase as a tool for production of prenylated indole derivatives


Recently, a gene for a 7-dimethylallyltryptophan synthase (7-DMATS) was identified in Aspergillus fumigatus and its enzymatic function was proven biochemically. In this study, the behaviour of 7-DMATS towards aromatic substrates was investigated and compared with that of the 4-dimethylallyltryptophan synthase FgaPT2 from the same fungus. In total, 24 simple indole derivatives were tested as potential substrates for 7-DMATS. With an exception of 7-methyltryptophan, all of the substances were accepted by 7-DMATS and converted to their prenylated derivatives, indicating a more flexible substrate specificity of 7-DMATS in comparison to that of FgaPT2. The relative activities of 7-DMATS towards these substrates were from 4% to 89% of that of L-tryptophan, much higher than that of FgaPT2. Structural elucidation of the isolated enzymatic products by nuclear magnetic resonance and mass spectrometry analysis proved unequivocally the prenylation at position C7 of the indole ring. Overnight incubation with eight substances showed that the conversion ratios were in the range of 55.9% to 99.7%. This study provided an additional example that prenylated indole derivatives can be effectively produced by using the overproduced and purified 7-DMATS.


Anika Kremer, Shu-Ming Li


Applied Microbiology and Biotechnology

Year, Volume, Page

2008, 79, 951



Tag Element Regiochemistry Product Substrate Cofactor Enzyme
PTDBREC00334 C Regular FgaPT2
PTDBREC00335 C Regular FgaPT2
PTDBREC00336 C Regular FgaPT2
PTDBREC00337 C Regular FgaPT2
PTDBREC00338 C Regular FgaPT2
PTDBREC00339 C Regular FgaPT2
PTDBREC00340 C Regular FgaPT2
PTDBREC00341 C Regular FgaPT2
PTDBREC00342 C Regular FgaPT2
PTDBREC00343 C Regular 7-DMATS
PTDBREC00344 C Regular 7-DMATS
PTDBREC00345 C Regular FgaPT2
PTDBREC00346 C Regular 7-DMATS
PTDBREC00347 C Regular 7-DMATS
PTDBREC00348 C Regular 7-DMATS
PTDBREC00349 C Regular 7-DMATS
PTDBREC00350 C Regular 7-DMATS
PTDBREC00351 C Regular 7-DMATS
PTDBREC00352 C Regular 7-DMATS
PTDBREC00353 C Regular 7-DMATS
PTDBREC00354 C Regular 7-DMATS
PTDBREC00355 C Regular 7-DMATS
PTDBREC00356 C Regular FgaPT2
PTDBREC00357 C Regular 7-DMATS
PTDBREC00358 C Regular 7-DMATS
PTDBREC00359 C Regular 7-DMATS
PTDBREC00360 C Regular 7-DMATS
PTDBREC00361 C Regular 7-DMATS
PTDBREC00362 C Regular FgaPT2
PTDBREC00363 C Regular FgaPT2
PTDBREC00364 C Regular FgaPT2
PTDBREC00365 C Regular FgaPT2
PTDBREC00366 C Regular FgaPT2
PTDBREC00367 C Regular FgaPT2
PTDBREC00368 C Regular FgaPT2
PTDBREC00369 C Regular FgaPT2
PTDBREC00370 C Regular FgaPT2
PTDBREC00371 C Regular FgaPT2
PTDBREC00372 C Regular FgaPT2
PTDBREC00373 C Regular FgaPT2
PTDBREC00374 C Regular FgaPT2
PTDBREC00375 C Regular FgaPT2
PTDBREC00376 C Regular FgaPT2
PTDBREC00377 C Regular FgaPT2
PTDBREC00378 C Regular FgaPT2
PTDBREC00379 C Regular 7-DMATS
PTDBREC00380 C Regular 7-DMATS
PTDBREC00381 C Regular 7-DMATS
PTDBREC00382 C Regular 7-DMATS
PTDBREC00383 C Regular 7-DMATS
PTDBREC00384 C Regular 7-DMATS
PTDBREC00385 C Regular 7-DMATS
PTDBREC00386 C Regular FgaPT2
PTDBREC00387 C Regular 7-DMATS
PTDBREC00388 C Regular 7-DMATS
PTDBREC00389 C Regular 7-DMATS
PTDBREC00390 C Regular 7-DMATS
PTDBREC00391 C Regular 7-DMATS
PTDBREC00392 C Regular 7-DMATS
PTDBREC00393 C Regular 7-DMATS
PTDBREC00394 C Regular 7-DMATS
PTDBREC00395 C Regular FgaPT2
PTDBREC00396 C Regular FgaPT2
PTDBREC00397 C Regular FgaPT2