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Literature summary for 4.1.2.38 extracted from

  • Peng, M.; Siebert, D.L.; Engqvist, M.K.M.; Niemeyer, C.M.; Rabe, K.S.
    Modeling-assisted design of thermostable benzaldehyde lyases from Rhodococcus erythropolis for continuous production of alpha-hydroxy ketones (2021), Chembiochem, 23, e202100468.
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
synthesis (R)-benzoin is synthesized from benzaldehyde using the most stable variant immobilized in packed-bed reactors via the SpyCatcher/SpyTag system. Over a period of seven days, (R)-benzoin is produced with a stable spacetime-yield of 9.3 mmol/l and day Rhodococcus erythropolis

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Rhodococcus erythropolis
expression in Escherichia coli Pseudomonas fluorescens

Crystallization (Commentary)

Crystallization (Comment) Organism
homology modeling shows a homotetrameric structure which can be described as a dimer of a dimers with four active sites Rhodococcus erythropolis

Protein Variants

Protein Variants Comment Organism
Q112A/E393A/S416G/T479A variant with larger but less polar binding site Rhodococcus erythropolis
Q112L/E393Y/S416G/T479F variant with binding site matched to Pseudomonas fluorescens enzyme Rhodococcus erythropolis

Organism

Organism UniProt Comment Textmining
Pseudomonas fluorescens P51853
-
-
Rhodococcus erythropolis
-
-
-
Rhodococcus erythropolis R138
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2 1H-indazole-6-carbaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-di(1H-indazol-6-yl)ethan-1-one
-
?
2 1H-indazole-6-carbaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-di(1H-indazol-6-yl)ethan-1-one
-
?
2 1H-indazole-6-carbaldehyde
-
Rhodococcus erythropolis R138 (2R)-2-hydroxy-1,2-di(1H-indazol-6-yl)ethan-1-one
-
?
2 1H-pyrrole-2-carbaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-di(1H-pyrrol-2-yl)ethan-1-one
-
?
2 1H-pyrrole-2-carbaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-di(1H-pyrrol-2-yl)ethan-1-one
-
?
2 1H-pyrrole-2-carbaldehyde
-
Rhodococcus erythropolis R138 (2R)-2-hydroxy-1,2-di(1H-pyrrol-2-yl)ethan-1-one
-
?
2 2-furaldehyde
-
Rhodococcus erythropolis (R)-2,2'-furoin
-
?
2 2-furaldehyde
-
Pseudomonas fluorescens (R)-2,2'-furoin
-
?
2 2-furaldehyde
-
Rhodococcus erythropolis R138 (R)-2,2'-furoin
-
?
2 3-hydroxy-4-methoxybenzaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-bis(3-hydroxy-4-methoxyphenyl)ethan-1-one
-
?
2 3-hydroxy-4-methoxybenzaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-bis(3-hydroxy-4-methoxyphenyl)ethan-1-one
-
?
2 3-hydroxy-4-methoxybenzaldehyde
-
Rhodococcus erythropolis R138 (2R)-2-hydroxy-1,2-bis(3-hydroxy-4-methoxyphenyl)ethan-1-one
-
?
2 4-formylbenzonitrile
-
Rhodococcus erythropolis 4,4'-[(1R)-1-hydroxy-2-oxoethane-1,2-diyl]dibenzonitrile
-
?
2 4-formylbenzonitrile
-
Pseudomonas fluorescens 4,4'-[(1R)-1-hydroxy-2-oxoethane-1,2-diyl]dibenzonitrile
-
?
2 4-formylbenzonitrile
-
Rhodococcus erythropolis R138 4,4'-[(1R)-1-hydroxy-2-oxoethane-1,2-diyl]dibenzonitrile
-
?
2 4-hydroxy-3-methoxybenzaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)ethan-1-one
-
?
2 4-hydroxy-3-methoxybenzaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-bis(4-hydroxy-3-methoxyphenyl)ethan-1-one
-
?
2 4-hydroxybenzaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one
-
?
2 4-hydroxybenzaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-bis(4-hydroxyphenyl)ethan-1-one
-
?
2 4-nitrobenzaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-bis(4-nitrophenyl)ethan-1-one
-
?
2 4-nitrobenzaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-bis(4-nitrophenyl)ethan-1-one
-
?
2 benzaldehyde
-
Rhodococcus erythropolis benzoin
-
?
2 benzaldehyde
-
Pseudomonas fluorescens benzoin
-
?
2 naphthalene-2-carbaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-di(naphthalen-2-yl)ethan-1-one
-
?
2 naphthalene-2-carbaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-di(naphthalen-2-yl)ethan-1-one
-
?
2 phenanthrene-9-carbaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-di(phenanthren-9-yl)ethan-1-one
-
?
2 phenanthrene-9-carbaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-di(phenanthren-9-yl)ethan-1-one
-
?
2 pyridine-3-carbaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-1,2-di(pyridin-3-yl)ethan-1-one
-
?
2 pyridine-3-carbaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-1,2-di(pyridin-3-yl)ethan-1-one
-
?
2-furaldehyde + 2,2-dimethoxyacetaldehyde
-
Rhodococcus erythropolis (2R)-1-(furan-2-yl)-2-hydroxy-3,3-dimethoxypropan-1-one
-
?
2-furaldehyde + 2,2-dimethoxyacetaldehyde
-
Pseudomonas fluorescens (2R)-1-(furan-2-yl)-2-hydroxy-3,3-dimethoxypropan-1-one
-
?
4-nitrobenzaldehyde + 2,2-dimethoxyacetaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-3,3-dimethoxy-1-(4-nitrophenyl)propan-1-one
-
?
benzaldehyde + 2,2-dimethoxyacetaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-3,3-dimethoxy-1-phenylpropan-1-one
-
?
benzaldehyde + 2,2-dimethoxyacetaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-3,3-dimethoxy-1-phenylpropan-1-one
-
?
naphthalene-2-carbaldehyde + 2,2-dimethoxyacetaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-3,3-dimethoxy-1-(naphthalen-2-yl)propan-1-one
-
?
naphthalene-2-carbaldehyde + 2,2-dimethoxyacetaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-3,3-dimethoxy-1-(naphthalen-2-yl)propan-1-one
-
?
pyridine-3-carbaldehyde + 2,2-dimethoxyacetaldehyde
-
Rhodococcus erythropolis (2R)-2-hydroxy-3,3-dimethoxy-1-(pyridin-3-yl)propan-1-one
-
?
pyridine-3-carbaldehyde + 2,2-dimethoxyacetaldehyde
-
Pseudomonas fluorescens (2R)-2-hydroxy-3,3-dimethoxy-1-(pyridin-3-yl)propan-1-one
-
?

Temperature Stability [°C]

Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
45.9
-
T50 value, i.e. 50% residual activity after 10 min Pseudomonas fluorescens
59.7
-
wild-type, T50 value, i.e. 50% residual activity after 10 min Rhodococcus erythropolis
66
-
mutant Q112L/E393Y/S416G/T479F , T50 value, i.e. 50% residual activity after 10 min Rhodococcus erythropolis
68.4
-
mutant Q112A/E393A/S416G/T479A, T50 value, i.e. 50% residual activity after 10 min Rhodococcus erythropolis

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
3 6 benzaldehyde mutant Q112L/E393Y/S416G/T479F, pH 8, 30°C Rhodococcus erythropolis
15
-
benzaldehyde wild-type, pH 8, 30°C Rhodococcus erythropolis
45
-
benzaldehyde mutant Q112L/E393Y/S416G/T479F, pH 8, 30°C Rhodococcus erythropolis
234
-
benzaldehyde pH 8, 30°C Pseudomonas fluorescens