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(2S,3R,4S)-4-hydroxy-L-isoleucine + 2-oxoglutarate + O2
(2S,3R)-2-amino-3-methyl-4-ketopentanoate + succinate + CO2
(S)-4-hydroxy-L-norvaline + 2-oxoglutarate + O2
?
(S)-allyl-L-cysteine + 2-oxoglutarate + O2
S-allyl-L-cysteine (S)-sulfoxide + succinate + CO2
(S)-ethyl-L-cysteine + 2-oxoglutarate + O2
S-ethyl-L-cysteine (S)-sulfoxide + succinate + CO2
(S)-methyl-L-cysteine + 2-oxoglutarate + O2
S-methyl-L-cysteine (S)-sulfoxide + succinate + CO2
4-hydroxy-L-norleucine + 2-oxoglutarate + O2
?
DL-homocysteine + 2-oxoglutarate + O2
?
-
-
-
-
?
L-allo-isoleucine + 2-oxoglutarate + O2
(S)-3-hydroxy-L-allo-isoleucine + succinate + CO2
-
-
-
-
?
L-cysteine + 2-oxoglutarate + O2
?
-
-
-
-
?
L-ethionine + 2-oxoglutarate + O2
L-ethionine (S)-sulfoxide + succinate + CO2
L-ethionine + 2-oxoglutarate + O2
L-ethionine sulfoxide + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-isoleucine + succinate + CO2
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
L-leucine + 2-oxoglutarate + O2
4-hydroxy-L-leucine + succinate + CO2
-
-
-
-
?
L-leucine + 2-oxoglutarate + O2
?
L-methionine + 2-oxoglutarate + O2
?
L-methionine + 2-oxoglutarate + O2
L-methionine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
L-methionine + 2-oxoglutarate + O2
L-methionine sulfoxide + succinate + CO2
-
-
-
-
?
L-norleucine + 2-oxoglutarate + O2
4-hydroxy-L-norleucine + succinate + CO2
-
-
-
-
?
L-norvaline + 2-oxoglutarate + O2
(S)-4-hydroxy-L-norvaline + succinate + CO2
-
-
-
-
?
additional information
?
-
(2S,3R,4S)-4-hydroxy-L-isoleucine + 2-oxoglutarate + O2
(2S,3R)-2-amino-3-methyl-4-ketopentanoate + succinate + CO2
-
-
-
-
?
(2S,3R,4S)-4-hydroxy-L-isoleucine + 2-oxoglutarate + O2
(2S,3R)-2-amino-3-methyl-4-ketopentanoate + succinate + CO2
-
-
-
-
?
(S)-4-hydroxy-L-norvaline + 2-oxoglutarate + O2
?
-
-
-
-
?
(S)-4-hydroxy-L-norvaline + 2-oxoglutarate + O2
?
-
-
-
-
?
(S)-allyl-L-cysteine + 2-oxoglutarate + O2
S-allyl-L-cysteine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
(S)-allyl-L-cysteine + 2-oxoglutarate + O2
S-allyl-L-cysteine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
(S)-ethyl-L-cysteine + 2-oxoglutarate + O2
S-ethyl-L-cysteine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
(S)-ethyl-L-cysteine + 2-oxoglutarate + O2
S-ethyl-L-cysteine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
(S)-methyl-L-cysteine + 2-oxoglutarate + O2
S-methyl-L-cysteine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
(S)-methyl-L-cysteine + 2-oxoglutarate + O2
S-methyl-L-cysteine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
4-hydroxy-L-norleucine + 2-oxoglutarate + O2
?
-
-
-
-
?
4-hydroxy-L-norleucine + 2-oxoglutarate + O2
?
-
-
-
-
?
L-ethionine + 2-oxoglutarate + O2
L-ethionine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
L-ethionine + 2-oxoglutarate + O2
L-ethionine (S)-sulfoxide + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
best substrate
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
best substrate
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-leucine + 2-oxoglutarate + O2
?
-
-
-
?
L-leucine + 2-oxoglutarate + O2
?
-
-
-
?
L-methionine + 2-oxoglutarate + O2
?
-
-
-
?
L-methionine + 2-oxoglutarate + O2
?
-
-
-
?
additional information
?
-
no activity with L-threonine
-
-
?
additional information
?
-
-
the enzyme does not react with D-Ile, D-allo-Ile, tert-butoxycarbonyl-L-Ile, 9-fluorenylmethoxycarbonyl-L-Ile,N-carbamoyl-L-Ile, L-Ile methyl ester, and N-acetyl-L-Ile methyl ester
-
-
?
additional information
?
-
no activity with L-threonine
-
-
?
additional information
?
-
-
the enzyme does not react with D-Ile, D-allo-Ile, tert-butoxycarbonyl-L-Ile, 9-fluorenylmethoxycarbonyl-L-Ile,N-carbamoyl-L-Ile, L-Ile methyl ester, and N-acetyl-L-Ile methyl ester
-
-
?
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(2S,3R,4S)-4-hydroxy-L-isoleucine + 2-oxoglutarate + O2
(2S,3R)-2-amino-3-methyl-4-ketopentanoate + succinate + CO2
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-isoleucine + succinate + CO2
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
(2S,3R,4S)-4-hydroxy-L-isoleucine + 2-oxoglutarate + O2
(2S,3R)-2-amino-3-methyl-4-ketopentanoate + succinate + CO2
-
-
-
-
?
(2S,3R,4S)-4-hydroxy-L-isoleucine + 2-oxoglutarate + O2
(2S,3R)-2-amino-3-methyl-4-ketopentanoate + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
best substrate
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
best substrate
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(2S,3R,4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
?
L-isoleucine + 2-oxoglutarate + O2
(4S)-4-hydroxy-L-isoleucine + succinate + CO2
-
-
-
-
?
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synthesis
development of efficient method for the biotransformation of 4-hydroxyisoleucine by resting cells expressing L27I/E80D/G169H/S182D 151.9 mM of 4-hydroxyisoleucine/l (22.4 g/l) can be synthesized in 12 h while the substrates seldom exhibits additional consumption
synthesis
-
double mutant I162T/T182N shows improvements in specific activity, protein expression level, and fermentation titer of 3.2-, 2.8-, and 9.4fold, respectively. L-Isoleucine (228 mM) is completely converted to (2S,3R,4S)-4-HIL with a space-time yield of up to 80.8 g/l and d. With a increase of the substrate loading to 1 M, a high conversion of 91% can also be achieved
synthesis
-
dynamic regulation of IDO expression by modified Ile biosensors increases the 4-HIL titer from 24.7 mM to 28.9?74.4 mM and may yield more 4-HIL than the static strain overexpressing IDO by the strong PtacM promoter (69.7 mM). Synergistic modulation of 2-oxoglutarate supply and O2 supply improves the 4-HIL production significantly, and the highest titer achieved is 135.3 mM
synthesis
improved synthesis of 4-HIL by ribosomal binding site engineering for gene expression in Corynebacterium glutamicum. To supply the cosubstrate 2-oxoglutarate at different levels, the OdhI gene is expressed using the ribosomal binding site sequences. The O2 supply is further enhanced in by overexpressing the Vgb gene. 4-HIL (up to 119.27 mM) is produced in the best strain. The synchronic supply of cosubstrates 2-oxoglutarate and O2 is critical for the high-yield production of 4-HIL
synthesis
improved synthesis of 4-HIL in an optimized strain of Corynebacterium glutamicum by application of programming adaptive laboratory evolution. The programming evolutionary system contains a Lys biosensor LysG-PlysE and an evolutionary actuator composed of a mutagenesis gene and a fluorescent protein gene. After successive rounds of evolution, mutant strains with significantly increased 4-HIL production and growth performance are obtained. The maximum 4-HIL titer is 152.19 mM, 28.4% higher than the starting strain
synthesis
-
in a genome-edited recombinant strain Escherichia coli BL21(DE3) DELTAsucABDeltaaceAK/pET-28a(+)-ido (2DELTA-ido), the bioconversion ratio of L-Ile to 4-HIL is enhanced by about 15% compared to Escherichia coli BL21(DE3)/pET-28a(+)-ido [BL21(DE3)-ido]
synthesis
-
recombinant Escherichia coli expressing mutant N126H/T130K or wild-type synthesizes 66.50 mM and 26.09 mM 4-hydroxyisoleucine, respectively, in 24 h
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Hibi, M.; Kawashima, T.; Kodera, T.; Smirnov, S.; Sokolov, P.; Sugiyama, M.; Shimizu, S.; Yokozeki, K.; Ogawa, J.
Characterization of Bacillus thuringiensis L-isoleucine dioxygenase for production of useful amino acids
Appl. Environ. Microbiol.
77
6926-6930
2011
Bacillus thuringiensis, Bacillus thuringiensis 2e2
brenda
Kodera, T.; Smirnov, S.; Samsonova, N.; Kozlov, Y.; Koyama, R.; Hibi, M.; Ogawa, J.; Yokozeki, K.; Shimizu, S.
A novel l-isoleucine hydroxylating enzyme, l-isoleucine dioxygenase from Bacillus thuringiensis, produces (2S,3R,4S)-4-hydroxyisoleucine
Biochem. Biophys. Res. Commun.
390
506-510
2009
Bacillus thuringiensis, Bacillus thuringiensis 2e2 AKU 0251
brenda
Smirnov, S.V.; Sokolov, P.M.; Kodera, T.; Sugiyama, M.; Hibi, M.; Shimizu, S.; Yokozeki, K.; Ogawa, J.
A novel family of bacterial dioxygenases that catalyse the hydroxylation of free L-amino acids
FEMS Microbiol. Lett.
331
97-104
2012
Bacillus thuringiensis (E2GIN1), Bacillus thuringiensis 2-e-2 (E2GIN1)
brenda
Hibi, M.; Kawashima, T.; Yajima, H.; Smirnov, S.; Kodera, T.; Sugiyama, M.; Shimizu, S.; Yokozeki, K.; Ogawa, J.
Enzymatic synthesis of chiral amino acid sulfoxides by Fe(II)/alpha-ketoglutarate-dependent dioxygenase
Tetrahedron Asymmetry
24
990-994
2013
Bacillus thuringiensis, Bacillus thuringiensis 2e2
-
brenda
Shi, F.; Niu, T.; Fang, H.
4-Hydroxyisoleucine production of recombinant Corynebacterium glutamicum ssp. lactofermentum under optimal corn steep liquor limitation
Appl. Microbiol. Biotechnol.
99
3851-3863
2015
Bacillus thuringiensis, Bacillus thuringiensis YBT-1520
brenda
Shi, F.; Fang, H.; Niu, T.; Lu, Z.
Overexpression of ppc and lysC to improve the production of 4-hydroxyisoleucine and its precursor L-isoleucine in recombinant Corynebacterium glutamicum ssp. lactofermentum
Enzyme Microb. Technol.
87-88
79-85
2016
Bacillus thuringiensis, Bacillus thuringiensis YBT-1520
brenda
Zhang, C.; Liu, Y.; Xue, N.; Wang, X.; Xie, X.; Xu, Q.; Chen, N.
Characterization of recombinant L-isoleucine-4-hydroxylase from Bacillus thuringiensis and its application in 4-hydroxyisoleucine biosynthesis
Wei Sheng Wu Xue Bao
54
889-896
2014
Bacillus thuringiensis (S5SPJ1), Bacillus thuringiensis TCCC 11826 (S5SPJ1)
brenda
An, J.; Zhang, W.; Jing, X.; Nie, Y.; Xu, Y.
Reconstitution of TCA cycle involving L-isoleucine dioxygenase for hydroxylation of L-isoleucine in Escherichia coli using CRISPR-Cas9
3 Biotech
10
167
2020
Bacillus sp. (in: Bacteria)
brenda
Tan, S.; Shi, F.; Liu, H.; Yu, X.; Wei, S.; Fan, Z.; Li, Y.
Dynamic control of 4-hydroxyisoleucine biosynthesis by modified L-isoleucine biosensor in recombinant Corynebacterium glutamicum
ACS Synth. Biol.
9
2378-2389
2020
Corynebacterium glutamicum
-
brenda
Yu, X.; Shi, F.; Liu, H.; Tan, S.; Li, Y.
Programming adaptive laboratory evolution of 4-hydroxyisoleucine production driven by a lysine biosensor in Corynebacterium glutamicum
AMB Express
11
66
2021
Bacillus thuringiensis (E2GIN1)
brenda
Zhang, C.; Ma, J.; Li, Z.; Liang, Y.; Xu, Q.; Xie, X.; Chen, N.
A strategy for L-isoleucine dioxygenase screening and 4-hydroxyisoleucine production by resting cells
Bioengineered
9
72-79
2018
Bacillus thuringiensis (S5SPJ1)
brenda
Huang, S.; Shi, F.
Directed evolution and site-specific mutagenesis of L-isoleucine dioxygenase derived from Bacillus weihenstephanensis
Biotechnol. Lett.
40
1227-1235
2018
Bacillus mycoides
brenda
Shi, F.; Fan, Z.; Zhang, S.; Wang, Y.; Tan, S.; Li, Y.
Optimization of ribosomal binding site sequences for gene expression and 4-hydroxyisoleucine biosynthesis in recombinant corynebacterium glutamicum
Enzyme Microb. Technol.
140
109622
2020
Bacillus thuringiensis (E2GIN1)
brenda
Du, P.; Yan, S.; Qian, X.L.; Pan, J.; Zhang, Z.J.; Yu, H.L.; Xu, J.H.
Engineering Bacillus subtilis isoleucine dioxygenase for efficient synthesis of (2S,3R,4S)-4-hydroxyisoleucine
J. Agric. Food Chem.
68
14555-14563
2020
Bacillus subtilis
brenda