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Literature summary for 3.1.1.1 extracted from

  • Wada, R., Kumon, T., Kourist, R., Ohta, H., Uemura, D., Yoshida, S., Miyamoto, K.
    Thermally driven asymmetric domino reaction catalyzed by a thermostable esterase and its variants (2013), Tetrahedron Lett., 54, 1921-1923.
No PubMed abstract available
Search for more literature for 3.1.1.1

Application

Application Comment Organism
synthesis synthesis of (S)-alpha-arylpropionates (profens). The reaction proceeds via enantioselective hydrolysis of the malonic acid ester to the monoester. Cleavage of the carboxyl group at the active site of the enzyme leads to the formation of the prochiral intermediate, which is then protonated to give the enantioenriched monoacid. Engineering of the active site gives rise to a variant with good stereoselectivity. As the esterase-catalyzed domino reaction does not need external cofactors and allows a theoretical yield of 100% Sulfurisphaera tokodaii

Cloned(Commentary)

Cloned (Comment) Organism
expressed in Escherichia coli Sulfurisphaera tokodaii

Protein Variants

Protein Variants Comment Organism
A179K increased stereoselectivity in synthesis of naproxen compared to the wild-type enzyme, (S)-selective, 64% enantioneric excess (compared to wild-type value 21% enantiomeric excess) Sulfurisphaera tokodaii
A179M/198E increased stereoselectivity in synthesis of naproxen compared to the wild-type enzyme, (S)-selective, 18% enantioneric excess (compared to wild-type value 21% enantiomeric excess) Sulfurisphaera tokodaii
A179M/198Y increased stereoselectivity in synthesis of naproxen compared to the wild-type enzyme, (S)-selective, 31% enantioneric excess (compared to wild-type value 21% enantiomeric excess) Sulfurisphaera tokodaii
I203E increased stereoselectivity in synthesis of naproxen compared to the wild-type enzyme, (S)-selective, 52% enantioneric excess (compared to wild-type value 21% enantiomeric excess) Sulfurisphaera tokodaii
I203R increased stereoselectivity in synthesis of naproxen compared to the wild-type enzyme, (S)-selective, 63% enantioneric excess (compared to wild-type value 21% enantiomeric excess) Sulfurisphaera tokodaii

Organism

Organism UniProt Comment Textmining
Sulfurisphaera tokodaii Q976W8
-
-
Sulfurisphaera tokodaii 7 Q976W8
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Sulfurisphaera tokodaii

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-nitrophenyl butyrate + H2O
-
 Sulfurisphaera tokodaii 4-nitrophenol + butyrate
-
 ?
4-nitrophenyl butyrate + H2O
-
 Sulfurisphaera tokodaii 7 4-nitrophenol + butyrate
-
 ?
diethyl (6-methoxynaphthalen-2-yl)(methyl)propanedioate + H2O
-
 Sulfurisphaera tokodaii ethanol + (2S)-3-ethoxy-2-(6-methoxynaphthalen-2-yl)-2-methyl-3-oxopropanoic acid
-
 ?
diethyl (6-methoxynaphthalen-2-yl)(methyl)propanedioate + H2O
-
 Sulfurisphaera tokodaii 7 ethanol + (2S)-3-ethoxy-2-(6-methoxynaphthalen-2-yl)-2-methyl-3-oxopropanoic acid
-
 ?
diethyl methyl(phenyl)propanedioate + H2O
-
 Sulfurisphaera tokodaii ethanol + (2S)-3-ethoxy-2-methyl-3-oxo-2-phenylpropanoic acid
-
 ?
diethyl methyl(phenyl)propanedioate + H2O
-
 Sulfurisphaera tokodaii 7 ethanol + (2S)-3-ethoxy-2-methyl-3-oxo-2-phenylpropanoic acid
-
 ?
ethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate + H2O
-
 Sulfurisphaera tokodaii ethanol + (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
-
 ?
ethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate + H2O
-
 Sulfurisphaera tokodaii 7 ethanol + (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
-
 ?
ethyl (2S)-2-phenylpropanoate + H2O
-
 Sulfurisphaera tokodaii ethanol + (2S)-2-phenylpropanoate
-
 ?
ethyl (2S)-2-phenylpropanoate + H2O
-
 Sulfurisphaera tokodaii 7 ethanol + (2S)-2-phenylpropanoate
-
 ?

Synonyms

Synonyms Comment Organism
Est0071
-
 Sulfurisphaera tokodaii
ST0071 locus name Sulfurisphaera tokodaii

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
70
-
 assay at Sulfurisphaera tokodaii

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7
-
 assay at Sulfurisphaera tokodaii