EC Number | Application | Comment | Organism |
---|---|---|---|
4.2.1.20 | synthesis | the reaction of mutant L166V with L-amino acid oxidase, halogenase enzymes and palladium chemocatalysts provides access to further D-configured and regioselectively halogenated or arylated beta-methyltryptophan derivatives | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | Cloned (Comment) | Organism |
---|---|---|
4.2.1.122 | recombinant expression of C-terminally His-tagged wild-type and mutant enzymes in Escherichia coli strain BL21(DE3) | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | Protein Variants | Comment | Organism |
---|---|---|---|
4.2.1.20 | L166A | mutation in beta-subunit, 3fold increase in catalytic efficiency with L-threonine as substrate, decrease in efficiency with L-serine | Salmonella enterica subsp. enterica serovar Typhimurium |
4.2.1.20 | L166V | mutation in beta-subunit, 7fold increase in catalytic efficiency with L-threonine as substrate, decrease in efficiency with L-serine | Salmonella enterica subsp. enterica serovar Typhimurium |
4.2.1.122 | L166A | site-directed mutagenesis the beta-subunit, the mutant shows altered substrate specificity compared to the wild-type enzyme | Salmonella enterica subsp. enterica serovar Typhimurium |
4.2.1.122 | L166V | site-directed mutagenesis of the beta-subunit, the mutant shows altered substrate specificity compared to the wild-type enzyme, single-step enzymatic synthesis of beta-methyl-Trp derivatives, overview. Although 2-, 4-, 6- or 7-substituted indoles are accepted by StTrpS beta-L66V, along with L-Thr, 5-subsituted indoles prove to be very poor substrates for the enzyme. Variant beta-L166V can better accommodate L-Thr as a substrate | Salmonella enterica subsp. enterica serovar Typhimurium |
4.2.1.122 | additional information | an engineered variant of tryptophan synthase from Salmonella enterica (StTrpS) can catalyse the efficient condensation of L-threonine and various indoles to generate bmTrp and derivatives in a single step. Although L-serine is the natural substrate for TrpS, targeted mutagenesis of the StTrpS active site provides a variant (bL166V) that can better accommodate L-Thr as a substrate. The condensation of L-Thr and indole proceeds with retention of configuration at both alpha- and beta-positions to give (2S,3S)-beta-methyl-Trp | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|---|
4.2.1.20 | 1.4 | - |
L-serine | mutant L166V, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 1.6 | - |
L-serine | wild-type, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 52 | - |
L-serine | mutant L166A, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 210 | - |
L-threonine | wild-type, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 310 | - |
L-threonine | mutant L166V, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 340 | - |
L-threonine | mutant L166A, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 1.4 | - |
L-serine | recombinant mutant L166V, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 1.6 | - |
L-serine | recombinant wild-type enzyme, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 52 | - |
L-serine | recombinant mutant L166A, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 210 | - |
L-threonine | recombinant wild-type enzyme, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 310 | - |
L-threonine | recombinant mutant L166V, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 340 | - |
L-threonine | recombinant mutant L166A, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|---|
4.2.1.122 | L-serine + indole | Salmonella enterica subsp. enterica serovar Typhimurium | L-serine is the preferred substrate | L-tryptophan + H2O | - |
? |
EC Number | Organism | UniProt | Comment | Textmining |
---|---|---|---|---|
4.2.1.20 | Salmonella enterica subsp. enterica serovar Typhimurium | - |
- |
- |
4.2.1.122 | Salmonella enterica subsp. enterica serovar Typhimurium | - |
- |
- |
4.2.1.122 | Salmonella enterica subsp. enterica serovar Typhimurium ATCC 37845 | - |
- |
- |
EC Number | Purification (Comment) | Organism |
---|---|---|
4.2.1.122 | recombinant C-terminally His-tagged wild-type and mutant enzymes from Escherichia coli strain BL21-A1(DE3) by nickel affinity chromatography, ultrafiltration, and desalting gel filtration | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | Reaction | Comment | Organism | Reaction ID |
---|---|---|---|---|
4.2.1.122 | L-serine + indole = L-tryptophan + H2O | reaction mechanism, overview | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|---|
4.2.1.20 | L-serine + indole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | L-tryptophan + H2O | - |
? | |
4.2.1.20 | L-serine + indole | - |
Salmonella enterica subsp. enterica serovar Typhimurium ATCC 37845 | L-tryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 2-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 2-methyl-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 2-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium ATCC 37845 | 2-methyl-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 4-fluoroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 4-fluoro-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 4-fluoroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium ATCC 37845 | 4-fluoro-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 4-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 4-methyl-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 4-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium ATCC 37845 | 4-methyl-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 6-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 6-methyl-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 7-chloroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 7-chloro-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 7-fluoroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 7-fluoro-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 7-methoxyindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 7-methoxy-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + 7-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | 7-methyl-(2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + indole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.20 | L-threonine + indole | - |
Salmonella enterica subsp. enterica serovar Typhimurium ATCC 37845 | (2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-serine + indole | L-serine is the preferred substrate | Salmonella enterica subsp. enterica serovar Typhimurium | L-tryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 2-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-2-methyl-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 4-fluoroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-4-fluoro-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 4-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-4-methyl-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 5-bromoindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-5-bromo-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 5-chloroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-5-chloro-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 5-phenylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-5-phenyl-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 6-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-6-methyl-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 7-chloroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-7-chloro-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 7-fluoroindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-7-fluoro-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 7-methoxyindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-7-methoxy-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + 7-methylindole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-7-methyl-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | L-threonine + indole | - |
Salmonella enterica subsp. enterica serovar Typhimurium | (2S,3S)-beta-methyltryptophan + H2O | - |
? | |
4.2.1.122 | additional information | activity and isolated yields of L-beta-methyl-Trp are low compared to the wild-type reaction with l-Ser, which gives over 90% of L-Trp under the same conditions. Preperative scale synthesis (2S,3S)-L-beta-methyl tryptophan and derivatives | Salmonella enterica subsp. enterica serovar Typhimurium | ? | - |
? |
EC Number | Synonyms | Comment | Organism |
---|---|---|---|
4.2.1.20 | TRPS | - |
Salmonella enterica subsp. enterica serovar Typhimurium |
4.2.1.122 | StTrpS (beta2) | - |
Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
---|---|---|---|---|
4.2.1.122 | 37 | - |
assay at | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|---|
4.2.1.20 | 0.0007 | - |
L-threonine | wild-type, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.0035 | - |
L-threonine | mutant L166A, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.007 | - |
L-threonine | mutant L166V, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.0817 | - |
L-serine | mutant L166V, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.183 | - |
L-serine | mutant L166A, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.35 | - |
L-serine | wild-type, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.00068 | - |
L-threonine | recombinant wild-type enzyme, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.0035 | - |
L-threonine | recombinant mutant L166A, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.007 | - |
L-threonine | recombinant mutant L166V, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.082 | - |
L-serine | recombinant mutant L166V, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.18 | - |
L-serine | recombinant mutant L166A, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.35 | - |
L-serine | recombinant wild-type enzyme, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
---|---|---|---|---|
4.2.1.122 | 7.8 | - |
assay at | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | General Information | Comment | Organism |
---|---|---|---|
4.2.1.122 | additional information | leucine residue Leu166 (betaL166) is in close proximity to the beta-position of the alpha-aminoacrylate species | Salmonella enterica subsp. enterica serovar Typhimurium |
EC Number | kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
---|---|---|---|---|---|---|
4.2.1.20 | 0.0000032 | - |
L-threonine | wild-type, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.0000102 | - |
L-threonine | mutant L166A, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.000023 | - |
L-threonine | mutant L166V, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.0037 | - |
L-serine | mutant L166A, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.06 | - |
L-serine | mutant L166V, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.20 | 0.217 | - |
L-serine | wild-type, pH not specified in the publication, temperature not specified in the publication | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.000003 | - |
L-threonine | recombinant wild-type enzyme, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.00001 | - |
L-threonine | recombinant mutant L166A, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.000023 | - |
L-threonine | recombinant mutant L166V, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.003 | - |
L-serine | recombinant mutant L166A, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.058 | - |
L-serine | recombinant mutant L166V, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium | |
4.2.1.122 | 0.22 | - |
L-serine | recombinant wild-type enzyme, pH 7.8, 37°C | Salmonella enterica subsp. enterica serovar Typhimurium |