2.5.1.122 (2E)-2-methylpenta-2,4-dien-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-2-methylpenta-2,4-dien-1-yl]-L-tyrosine + diphosphate - ? 457373 2.5.1.122 (2E)-3-(2-methoxyphenyl)prop-2-en-1-yl trihydrogen diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-3-(2-methoxyphenyl)prop-2-en-1-yl]-L-tyrosine + diphosphate - ? 457374 2.5.1.122 (2E)-3-methylpent-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-3-methylpent-2-en-1-yl]-L-tyrosine + diphosphate - ? 457376 2.5.1.122 (2E)-3-phenylbut-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-3-phenylbut-2-en-1-yl]-L-tyrosine + diphosphate - ? 457377 2.5.1.122 (2E)-3-phenylprop-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-3-phenylprop-2-en-1-yl]-L-tyrosine + diphosphate - ? 457378 2.5.1.122 (2E)-5-methylhexa-2,4-dien-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-5-methylhexa-2,4-dien-1-yl]-L-tyrosine + diphosphate - ? 457380 2.5.1.122 (2E)-but-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-but-2-en-1-yl]-L-tyrosine + diphosphate - ? 457382 2.5.1.122 (2E)-penta-2,4-dien-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E)-penta-2,4-dien-1-yl]-L-tyrosine + diphosphate - ? 457384 2.5.1.122 (2E,4E)-2-methylhexa-2,4-dien-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E,4E)-2-methylhexa-2,4-dien-1-yl]-L-tyrosine + diphosphate - ? 457390 2.5.1.122 (2E,4E)-5-phenylpenta-2,4-dien-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2E,4E)-5-phenylpenta-2,4-dien-1-yl]-L-tyrosine + diphosphate - ? 457389 2.5.1.122 (2Z)-3-chlorobut-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[(2Z)-3-chlorobut-2-en-1-yl]-L-tyrosine + diphosphate - ? 457395 2.5.1.122 2-cyclohexylideneethyl diphosphate + L-tyrosine - Leptosphaeria maculans O-[2-cyclohexylideneethyl]-L-tyrosine + diphosphate - ? 457532 2.5.1.122 2-methylprop-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[2-methylprop-2-en-1-yl]-L-tyrosine + diphosphate - ? 457555 2.5.1.122 2-oxopropyl diphosphate + L-tyrosine - Leptosphaeria maculans O-[2-oxopropyl]-L-tyrosine + diphosphate - ? 457585 2.5.1.122 2-pentenyl diphosphate + 3-fluoro-DL-tyrosine - Leptosphaeria maculans diphosphate + 3-fluoro-4-O-(2-pentenyl)-DL-tyrosine 20.5% conversion ? 436799 2.5.1.122 2-pentenyl diphosphate + 3-fluoro-DL-tyrosine - Aspergillus niger diphosphate + 3-fluoro-4-O-(2-pentenyl)-DL-tyrosine 43.9% conversion ? 436799 2.5.1.122 2-pentenyl diphosphate + 4-amino-L-phenylalanine - Leptosphaeria maculans diphosphate + 4-(2-pentenylamino)-L-phenylalanine 42.6% conversion ? 436800 2.5.1.122 2-pentenyl diphosphate + 4-amino-L-phenylalanine - Aspergillus niger diphosphate + 4-(2-pentenylamino)-L-phenylalanine 46.4% conversion ? 436800 2.5.1.122 2-pentenyl diphosphate + alpha-methyl-L-tyrosine - Aspergillus niger diphosphate + alpha-methyl-4-O-(2-pentenyl)-L-tyrosine 10.3% conversion ? 436801 2.5.1.122 2-pentenyl diphosphate + alpha-methyl-L-tyrosine - Leptosphaeria maculans diphosphate + alpha-methyl-4-O-(2-pentenyl)-L-tyrosine 33.5% conversion ? 436801 2.5.1.122 2-pentenyl diphosphate + L-tyrosine - Leptosphaeria maculans diphosphate + 4-O-(2-pentenyl)-L-tyrosine 44.3% conversion ? 436805 2.5.1.122 2-pentenyl diphosphate + L-tyrosine - Aspergillus niger diphosphate + 4-O-(2-pentenyl)-L-tyrosine 56.6% conversion ? 436805 2.5.1.122 3,3-diphenylprop-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[3,3-diphenylprop-2-en-1-yl]-L-tyrosine + diphosphate - ? 457593 2.5.1.122 3-ethylpent-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[3-ethylpent-2-en-1-yl]-L-tyrosine + diphosphate - ? 457605 2.5.1.122 benzyl diphosphate + 4-amino-L-phenylalanine - Leptosphaeria maculans diphosphate + 4-(benzylamino)-L-phenylalanine 54.6% conversion ? 437211 2.5.1.122 benzyl diphosphate + 4-amino-L-phenylalanine - Aspergillus niger diphosphate + 4-(benzylamino)-L-phenylalanine 67.2% conversion ? 437211 2.5.1.122 cyanomethyl diphosphate + L-tyrosine - Leptosphaeria maculans O-[cyanomethyl]-L-tyrosine + diphosphate - ? 457886 2.5.1.122 cyclohex-1-en-1-ylmethyl diphosphate + L-tyrosine - Leptosphaeria maculans O-[cyclohex-1-en-1-ylmethyl]-L-tyrosine + diphosphate - ? 457887 2.5.1.122 dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine 98% activity compared to 3-iodo-L-tyrosine Aspergillus niger ? - ? 430120 2.5.1.122 dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine - Aspergillus niger diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine 100% conversion ? 437404 2.5.1.122 dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine - Leptosphaeria maculans diphosphate + 3-hydroxy-4-dimethylallyloxy-L-phenylalanine 88.2% conversion ? 437404 2.5.1.122 dimethylallyl diphosphate + 3,4-dihydroxy-L-phenylalanine - Aspergillus niger diphosphate + ? - ? 437405 2.5.1.122 dimethylallyl diphosphate + 3,5-dibromo-4-hydroxy-L-phenylalanine - Aspergillus niger diphosphate + 3,5-dibromo-4-dimethylallyloxy-L-phenylalanine 20.6% conversion ? 437406 2.5.1.122 dimethylallyl diphosphate + 3,5-dibromo-4-hydroxy-L-phenylalanine - Leptosphaeria maculans diphosphate + 3,5-dibromo-4-dimethylallyloxy-L-phenylalanine 53.3% conversion ? 437406 2.5.1.122 dimethylallyl diphosphate + 3-amino-L-tyrosine SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Amino-L-tyrosine is prenylated with 108% of the activity compared to L-tyrosine Leptosphaeria maculans diphosphate + 3-amino-4-O-dimethylallyl-L-tyrosine - ? 426308 2.5.1.122 dimethylallyl diphosphate + 3-fluoro-DL-tyrosine SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Iodo-L-tyrosine is prenylated with 53.6% of the activity compared to L-tyrosine Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-3-fluoro-DL-tyrosine - ? 426309 2.5.1.122 dimethylallyl diphosphate + 3-fluoro-DL-tyrosine 53% activity compared to 3-iodo-L-tyrosine Aspergillus niger ? - ? 430121 2.5.1.122 dimethylallyl diphosphate + 3-fluoro-DL-tyrosine - Aspergillus niger diphosphate + 3-fluoro-4-O-dimethylallyl-DL-tyrosine 50.1% conversion ? 437407 2.5.1.122 dimethylallyl diphosphate + 3-fluoro-DL-tyrosine - Leptosphaeria maculans diphosphate + 3-fluoro-4-O-dimethylallyl-DL-tyrosine 66.5% conversion ? 437407 2.5.1.122 dimethylallyl diphosphate + 3-iodo-L-tyrosine SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives. 3-Iodo-L-tyrosine is prenylated with 27.3% of the activity compared to L-tyrosine Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-3-iodo-L-tyrosine - ? 426310 2.5.1.122 dimethylallyl diphosphate + 3-iodo-L-tyrosine 100% activity Aspergillus niger ? - ? 430122 2.5.1.122 dimethylallyl diphosphate + 3-iodo-L-tyrosine - Aspergillus niger diphosphate + 3-iodo-4-O-dimethylallyl-L-tyrosine 100% conversion ? 437409 2.5.1.122 dimethylallyl diphosphate + 3-iodo-L-tyrosine - Leptosphaeria maculans diphosphate + 3-iodo-4-O-dimethylallyl-L-tyrosine 100% conversion ? 437409 2.5.1.122 dimethylallyl diphosphate + 3-iodo-L-tyrosine - Aspergillus niger diphosphate + ? - ? 437410 2.5.1.122 dimethylallyl diphosphate + 4-amino-L-phenylalanine 23% activity compared to 3-iodo-L-tyrosine Aspergillus niger ? - ? 430123 2.5.1.122 dimethylallyl diphosphate + 4-amino-L-phenylalanine - Leptosphaeria maculans diphosphate + 4-(dimethylallylamino)-L-phenylalanine 66.1% conversion ? 437411 2.5.1.122 dimethylallyl diphosphate + 4-amino-L-phenylalanine - Aspergillus niger diphosphate + 4-(dimethylallylamino)-L-phenylalanine 78.1% conversion ? 437411 2.5.1.122 dimethylallyl diphosphate + 4-amino-L-phenylalanine prenylation at 4-O- or N-atom Aspergillus niger diphosphate + 4-dimethylallylamino-L-phenylalanine - ? 437414 2.5.1.122 dimethylallyl diphosphate + 4-methyl-DL-tryptophan 13% activity compared to 3-iodo-L-tyrosine Aspergillus niger ? - ? 430124 2.5.1.122 dimethylallyl diphosphate + 4-methyl-DL-tryptophan 41% activity compared to 3-iodo-L-tyrosine Aspergillus niger diphosphate + 7-dimethylallyl-4-methyl-L-tryptophan - ? 430125 2.5.1.122 dimethylallyl diphosphate + 5-methyl-DL-tryptophan 10% activity compared to 3-iodo-L-tyrosine Aspergillus niger diphosphate + 7-dimethylally-5-methyl-L-tryptophan - ? 430126 2.5.1.122 dimethylallyl diphosphate + alpha-methyl-L-tyrosine 98% activity compared to 3-iodo-L-tyrosine Aspergillus niger ? - ? 430127 2.5.1.122 dimethylallyl diphosphate + alpha-methyl-L-tyrosine - Leptosphaeria maculans diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine 89.4% conversion ? 437438 2.5.1.122 dimethylallyl diphosphate + alpha-methyl-L-tyrosine - Aspergillus niger diphosphate + alpha-methyl-4-O-dimethylallyl-L-tyrosine 98.3% conversion ? 437438 2.5.1.122 dimethylallyl diphosphate + D-tyrosine 33% activity compared to 3-iodo-L-tyrosine Aspergillus niger ? - ? 430128 2.5.1.122 dimethylallyl diphosphate + D-tyrosine - Aspergillus niger diphosphate + 4-O-dimethylallyl-D-tyrosine - ? 437479 2.5.1.122 dimethylallyl diphosphate + D-tyrosine - Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-D-tyrosine 57.6% conversion ? 437479 2.5.1.122 dimethylallyl diphosphate + D-tyrosine - Aspergillus niger diphosphate + 4-O-dimethylallyl-D-tyrosine 59.5% conversion ? 437479 2.5.1.122 dimethylallyl diphosphate + L-3,4-dihydroxyphenylalanine 16.6% of the activity, compared to L-tyrosine. It is expected that the prenylation takes place at the 4-hydroxyl group. The structure of the product is not determined Leptosphaeria maculans ? - ? 426321 2.5.1.122 dimethylallyl diphosphate + L-o-tyrosine C-5 prenylation Aspergillus niger diphosphate + 5-(3-methylbut-2-enyl)-L-o-tyrosine - ? 437496 2.5.1.122 dimethylallyl diphosphate + L-tryptophan C-7 prenylation Aspergillus niger diphosphate + 7-(3-methylbut-2-enyl)-L-tryptophan - ? 421955 2.5.1.122 dimethylallyl diphosphate + L-tryptophan reverse prenylation Leptosphaeria maculans diphosphate + 1-(2-methylbut-3-en-2-yl)-L-tryptophan - ? 426322 2.5.1.122 dimethylallyl diphosphate + L-tryptophan catalytic efficiency for L-tryptophan is 6% compared to catalytic efficiency for L-tyrosine Leptosphaeria maculans diphosphate + 7-dimethylallyltryptophan - ? 426323 2.5.1.122 dimethylallyl diphosphate + L-tryptophan - Leptosphaeria maculans diphosphate + 7-dimethylallyl-L-tryptophan - ? 430129 2.5.1.122 dimethylallyl diphosphate + L-tryptophan 33% activity compared to 3-iodo-L-tyrosine Aspergillus niger diphosphate + 7-dimethylallyl-L-tryptophan - ? 430129 2.5.1.122 dimethylallyl diphosphate + L-tyrosine - Aspergillus fumigatus diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine - Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine - Aspergillus niger diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine - Aspergillus niger diphosphate + 4-O-dimethylallyl-L-tyrosine 89.1% conversion ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine - Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-L-tyrosine 99.3% conversion ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine first committed step in the biosynthesis of the phytotoxin sirodesmin PL Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine the enzyme is involved in biosynthesis of sirodesmin PL Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine the enzyme is involved in biosynthesis of the phytotoxin sirodesmin PL Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine no activity with cyclo-L-Tyr-L-Ser, L-Phe, 4-hydroxybenzoate or 4-coumarate Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine SirD catalyzes the regiospecific O-prenylation at position C4 of tyrosine and derivatives Leptosphaeria maculans diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine 98% activity compared to 3-iodo-L-tyrosine Aspergillus niger diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 dimethylallyl diphosphate + L-tyrosine O-4 prenylation Aspergillus niger diphosphate + 4-O-dimethylallyl-L-tyrosine - ? 424780 2.5.1.122 methylallyl diphosphate + 4-amino-L-phenylalanine - Leptosphaeria maculans diphosphate + 4-(methylallylamino)-L-phenylalanine 34.8% conversion ? 437702 2.5.1.122 methylallyl diphosphate + 4-amino-L-phenylalanine - Aspergillus niger diphosphate + 4-(methylallylamino)-L-phenylalanine 57.7% conversion ? 437702 2.5.1.122 methylallyl diphosphate + L-tyrosine - Leptosphaeria maculans diphosphate + 4-O-methylallyl-L-tyrosine 28% conversion ? 437709 2.5.1.122 methylallyl diphosphate + L-tyrosine - Aspergillus niger diphosphate + 4-O-methylallyl-L-tyrosine 21.2% conversion ? 437709 2.5.1.122 additional information SirD also catalyses the C-prenylation of L-Trp derivatives, in addition to the O-prenylation Leptosphaeria maculans ? - ? 89 2.5.1.122 additional information SirD also prenylates L-Trp, resulting in the formation of 7-dimethylallyltryptophan. SirD catalyses the C-prenylation of L-Trp, in addition to the O-prenylation of L-Tyr, cf. EC 2.5.1.34 Leptosphaeria maculans ? - ? 89 2.5.1.122 additional information the catalytic erfficiency with 4-mercapto-L-phenylalanine, 4-methoxy-L-tryptophan and 7-methyl-L-tryptophan is less than 1% of the reaction with L-tyrosine Leptosphaeria maculans ? - ? 89 2.5.1.122 additional information no activity with 1-naphthol, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 3,5-dihydroxy-2-naphthoic acid, and 3,7-dihydroxy-2-naphthoic acid Leptosphaeria maculans ? - ? 89 2.5.1.122 additional information HR-ESI-MS and NMR product analysis. No activity with L-m-tyrosine Aspergillus niger ? - ? 89 2.5.1.122 additional information in presence of unnatural dimethylallyl diphosphate analogs such as methylallyl, 2-pentenyl and benzyl diphosphate for alkylation, or benzylation of the indole ring enzyme catalyzes the regiospecific O- or N-alkylation or benzylation at position C4 of the aromatic ring Aspergillus niger ? - ? 89 2.5.1.122 additional information in presence of unnatural dimethylallyl diphosphate analogs such as methylallyl, 2-pentenyl and benzyl diphosphate for alkylation, or benzylation of the indole ring enzyme catalyzes the regiospecific O- or N-alkylation or benzylation at position C4 of the aromatic ring Leptosphaeria maculans ? - ? 89 2.5.1.122 additional information the enzyme catalyzes C7-prenylation of the indole ring, EC 2.5.1.80, but also accepts L-tyrosine as substrate and converts it to an O-prenylated derivative, EC 2.5.1.122. 7-DMATS is able to take L-tyrosine and two derivatives thereof as substrates and catalyzed the same O- or N-prenylation Aspergillus fumigatus ? - ? 89 2.5.1.122 additional information the enzyme shows a wider substrate spectrum compared to tyrosine prenyltransferase SirD. It catalyzes O-prenylation of L-tyrosine, EC 2.5.1.122, and also accepts 4-amino-L-phenylalanine for an N-prenylation and L-tryptophan for a C7-prenylation, EC 2.5.1.80. It is also active with 4-amino-L-phenylalanine as well as 4- and 5-methyl-DL-tryptophan. HRMS analysis of the enzyme products, overview. 3,5-dibromo-L-tyrosine is a poor substrate Aspergillus niger ? - ? 89 2.5.1.122 prop-2-en-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[prop-2-en-1-yl]-L-tyrosine + diphosphate - ? 458182 2.5.1.122 prop-2-yn-1-yl diphosphate + L-tyrosine - Leptosphaeria maculans O-[prop-2-yn-1-yl]-L-tyrosine + diphosphate - ? 458183