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Literature summary for 1.4.3.12 extracted from
- Accessing D-valine synthesis by improved variants of bacterial cyclohexylamine oxidase (2018), ChemCatChem, 10, 387-390 .
No PubMed abstract available
Application
| Application | Comment | Organism |
|---|---|---|
| synthesis | chemoenzymatic deracemization is applied to prepare D-valine from racemic valine ethyl ester or L-valine ethyl ester in high yield (up to 95%) with excellent optical purity (more than 99% enantiomeric excess) by employing cyclohexylamine oxidase (CHAO) variant Y321I/M226T exhibiting catalytic efficiency that is 30times higher than that of the wild type enzyme | Microbacterium oxydans |
Protein Variants
| Protein Variants | Comment | Organism |
|---|---|---|
| L199F | 2.1fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme | Microbacterium oxydans |
| M226T | 1.3fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme | Microbacterium oxydans |
| T198I | 2.55fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme | Microbacterium oxydans |
| Y321I | 13fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme | Microbacterium oxydans |
| Y321I/ M226T | 29.8fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme. Chemoenzymatic deracemization is applied to prepare D-valine from racemic valine ethyl ester or L-valine ethyl ester in high yield (up to 95%) with excellent optical purity (more than 99% enantiomeric excess) by employing cyclohexylamine oxidase (CHAO) variant Y321I/M226T exhibiting catalytic efficiency that is 30 times higher than that of the wild type enzyme | Microbacterium oxydans |
| Y321I/ M226T/L199F | mutant failed to be expressed | Microbacterium oxydans |
| Y321I/L199F | mutant failed to be expressed | Microbacterium oxydans |
| Y321I/M226T/T198I | 15.1fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme | Microbacterium oxydans |
| Y321I/M226T/T198I/F199F | 7.5fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme | Microbacterium oxydans |
| Y321I/T198I | 14.2fold increase of kcat/Km for the substrate L-valine ethyl ester as compared to wild-type enzyme | Microbacterium oxydans |
KM Value [mM]
| KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 1.1 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I | Microbacterium oxydans | |
| 1.2 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/ M226T | Microbacterium oxydans | |
| 1.8 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/T198I | Microbacterium oxydans | |
| 2.7 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/M226T/T198I | Microbacterium oxydans | |
| 5 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme T198I | Microbacterium oxydans | |
| 5.1 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme M226T | Microbacterium oxydans | |
| 5.2 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme L199F | Microbacterium oxydans | |
| 5.8 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/M226T/T198I/F199F | Microbacterium oxydans | |
| 7.5 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, wild-type enzyme | Microbacterium oxydans |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Microbacterium oxydans | - |
- |
- |
| Microbacterium oxydans IH-35A | - |
- |
- |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| L-valine ethyl ester | isomerization reaction | Microbacterium oxydans | D-valine ethyl ester | - |
? |  |
| L-valine ethyl ester | isomerization reaction | Microbacterium oxydans IH-35A | D-valine ethyl ester | - |
? | |
| racemic phenylalanine ethyl ester | deracemization reaction | Microbacterium oxydans | L-phenylalanine ethyl ester | - |
? | |
| racemic phenylalanine ethyl ester | deracemization reaction | Microbacterium oxydans IH-35A | L-phenylalanine ethyl ester | - |
? | |
| racemic valine ethyl ester | deracemization reaction | Microbacterium oxydans | D-valine ethyl ester | - |
? | |
| racemic valine ethyl ester | deracemization reaction | Microbacterium oxydans IH-35A | D-valine ethyl ester | - |
? | |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| CHAO | - |
Microbacterium oxydans |
Turnover Number [1/s]
| Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.55 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme M226T | Microbacterium oxydans | |
| 0.64 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, wild-type enzyme | Microbacterium oxydans | |
| 0.92 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme L199F | Microbacterium oxydans | |
| 1.09 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme T198I | Microbacterium oxydans | |
| 1.25 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I | Microbacterium oxydans | |
| 2.18 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/T198I | Microbacterium oxydans | |
| 3.1 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/ M226T | Microbacterium oxydans | |
| 3.54 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/M226T/T198I | Microbacterium oxydans | |
| 3.69 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/M226T/T198I/F199F | Microbacterium oxydans |
kcat/KM [mM/s]
| kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|
| 0.085 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, wild-type enzyme | Microbacterium oxydans | |
| 0.108 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme M226T | Microbacterium oxydans | |
| 0.18 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme L199F | Microbacterium oxydans | |
| 0.22 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme T198I | Microbacterium oxydans | |
| 0.64 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/M226T/T198I/F199F | Microbacterium oxydans | |
| 1.1 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I | Microbacterium oxydans | |
| 1.2 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/T198I | Microbacterium oxydans | |
| 1.3 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/M226T/T198I | Microbacterium oxydans | |
| 2.54 | - |
L-valine ethyl ester | pH and temperature not specified in the publication, mutant enzyme Y321I/ M226T | Microbacterium oxydans |
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