A novel l-isoleucine hydroxylating enzyme, l-isoleucine dioxygenase from Bacillus thuringiensis, produces (2S,3R,4S)-4-hydroxyisoleucine

Kodera, Tomohiro; Smirnov, Sergey V.; Samsonova, Natalya N.; Kozlov, Yury I.; Koyama, Ryokichi; Hibi, Makoto; Ogawa, Jun; Yokozeki, Kenzo; Shimizu, Sakayu

doi:10.1016/j.bbrc.2009.09.126

Cited by 72 publications

(77 citation statements)

References 15 publications

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“…The optimal reaction conditions for the reaction by recombinant IDO were pH 6.0 and 25°C. Although the optimal reaction pH of recombinant IDO was the same as that of the native form of the IDO purified from B. thuringiensis 2e2 cells, its optimal reaction temperature was 5°C lower than that of the native form (18). Addition of a 6ϫHis tag to the C terminus of IDO may therefore influence its thermostability.…”

Section: Catalytic Properties Of Recombinant Idomentioning

confidence: 99%

“…In our previous research, it was found that Bacillus thuringiensis 2e2 possessed a novel L-isoleucine (L-Ile) metabolic pathway involving the hydroxylation of L-Ile to (2S,3R,4S)-HIL and further oxidation to (2S,3R)-2-amino-3-methyl-4-ketopentanoate (AMKP), which is known as a vitamin B 12 antimetabolite (27). The former reaction of the pathway was catalyzed by an ␣-ketoglutarate (␣KG)-dependent L-Ile dioxygenase (IDO) (18) and the latter by a NAD ϩ -dependent HIL dehydrogenase (23). In addition, we developed an efficient production system for HIL using Escherichia coli cells heterologously expressing IDO (31).…”

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confidence: 99%

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Characterization of Bacillus thuringiensis l -Isoleucine Dioxygenase for Production of Useful Amino Acids

Hibi

Kawashima

Kodera

et al. 2011

Appl Environ Microbiol

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We determined the enzymatic characteristics of an industrially important biocatalyst, ␣-ketoglutaratedependent L-isoleucine dioxygenase (IDO), which was found to be the enzyme responsible for the generation of (2S,3R,4S)-4-hydroxyisoleucine in Bacillus thuringiensis 2e2. Depending on the amino acid used as the substrate, IDO catalyzed three different types of oxidation reactions: hydroxylation, dehydrogenation, and sulfoxidation. IDO stereoselectively hydroxylated several hydrophobic aliphatic L-amino acids, as well as L-isoleucine, and produced (S)-3-hydroxy-L-allo-isoleucine, 4-hydroxy-L-leucine, (S)-4-hydroxy-L-norvaline, 4-hydroxy-L-norleucine, and 5-hydroxy-L-norleucine. The IDO reaction product of L-isoleucine, (2S,3R,4S)-4-hydroxyisoleucine, was again reacted with IDO and dehydrogenated into (2S,3R)-2-amino-3-methyl-4-ketopentanoate, which is also a metabolite found in B. thuringiensis 2e2. Interestingly, IDO catalyzed the sulfoxidation of some sulfur-containing L-amino acids and generated L-methionine sulfoxide and L-ethionine sulfoxide. Consequently, the effective production of various modified amino acids would be possible using IDO as the biocatalyst.Hydroxy amino acids are unusual hydroxylated amino acids and are ubiquitous in nature. They exist as secondary metabolites and components of peptides and proteins. Free amino acids are mostly found in higher plants (3,29), and also, free threo-3-hydroxy-L-asparagine has been found in human urine (25) and free 3-hydroxy-

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Section: Catalytic Properties Of Recombinant Idomentioning

confidence: 99%

mentioning

confidence: 99%

Characterization of Bacillus thuringiensis l -Isoleucine Dioxygenase for Production of Useful Amino Acids

Hibi

Kawashima

Kodera

et al. 2011

Appl Environ Microbiol

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“…According to the previous researches, the N-terminal amino acid residue of the mature IDO isolated from B. thuringiensis strain 2e2 was Lys, and the first 6 amino acid residues of the initially translated protein (MTFVLS) were cleaved to generate the mature form (Kodera et al 2009;Smirnov et al 2010). Therefore, the truncated IdoΔ6 which lacks the 2-6 amino acid residues was then expressed in C. glutamicum ssp.…”

Section: Effects Of Corn Steep Liquor Supplementation On 4-hil Producmentioning

confidence: 99%

“…Therefore, a more efficient method for biosynthesis of 4-HIL is desirable. Recently, a new enzymatic method based on Bacillus thuringiensis-derived L-isoleucine dioxygenase (IDO) was reported for direct biosynthesis of 4-HIL from Lisoleucine (Ile) (Kodera et al 2009;Ogawa et al 2011;Hibi et al 2011). IDO catalyzes the C-4 hydroxylation of Ile to form 4-HIL with the concomitant oxidation of α-ketoglutarate (KG) to form succinate.…”

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4-Hydroxyisoleucine production of recombinant Corynebacterium glutamicum ssp. lactofermentum under optimal corn steep liquor limitation

Shi

Niu

Fang

2015

Appl Microbiol Biotechnol

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4-Hydroxyisoleucine (4-HIL) is a nonproteinogenic amino acid that exhibits insulinotropic biological activity. Here, L-isoleucine dioxygenase gene (ido) derived from Bacillus thuringiensis YBT-1520 was cloned and expressed in an L-isoleucine-producing strain, Corynebacterium glutamicum ssp. lactofermentum SN01, in order to directly convert its endogenous L-isoleucine (Ile) into 4-HIL through single-step fermentation. The effects of corn steep liquor limitation as well as ido and truncated idoΔ6 overexpression on 4-HIL production were researched. 4-HIL production by ido-overexpressing strain was improved to 65.44 ± 2.27 mM after fermented for 144 h under corn steep liquor-subsufficient condition, obviously higher than that under corn steep liquor-rich and insufficient conditions. The conversion ratio of Ile to 4-HIL increased to 0.85 mol/mol. In addition, 4-HIL production by ido-overexpressing strain was higher than that by idoΔ6-overexpressing strain, in accord with the relatively higher affinity of Ido as compared to IdoΔ6. This research generated a novel system for 4-HIL de novo biosynthesis and demonstrated corn steep liquor limitation as a useful strategy for improving 4-HIL production in recombinant C. glutamicum ssp. lactofermentum.

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“…31) For example, (2S,3R,4S)-4-hydroxyisoleucine has insulinotropic and anti-obesity effects and seems to have potential for the treatment of diabetes. 32) In addition, cis-4-hydroxy-proline has been clinically evaluated as an anticancer drug. 33) A Fe(II)-and α-KG-dependent dioxygenase from Burkholderia ambifaria AMMD, SadA, is useful as a biocatalyst for the (R)-selective hydroxylation at the C3 position of N-substituted branched-chain L-amino acids.…”

Section: Stereoselective Catalytic Mechanism Of Dioxygenase and mentioning

confidence: 99%

Structural analysis of enzymes used for bioindustry and bioremediation

Tanokura

Miyakawa

Guan

et al. 2015

Bioscience, Biotechnology, and Biochemistry

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Microbial enzymes have been widely applied in the large-scale, bioindustrial manufacture of food products and pharmaceuticals due to their high substrate specificity and stereoselectivity, and their effectiveness under mild conditions with low environmental burden. At the same time, bioremedial techniques using microbial enzymes have been developed to solve the problem of industrial waste, particularly with respect to persistent chemicals and toxic substances. And finally, structural studies of these enzymes have revealed the mechanistic basis of enzymatic reactions, including the stereoselectivity and binding specificity of substrates and cofactors. The obtained structural insights are useful not only to deepen our understanding of enzymes with potential bioindustrial and/or bioremedial application, but also for the functional improvement of enzymes through rational protein engineering. This review shows the structural bases for various types of enzymatic reactions, including the substrate specificity accompanying cofactor-controlled and kinetic mechanisms.

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A novel l-isoleucine hydroxylating enzyme, l-isoleucine dioxygenase from Bacillus thuringiensis, produces (2S,3R,4S)-4-hydroxyisoleucine

Cited by 72 publications

References 15 publications

Characterization of Bacillus thuringiensis l -Isoleucine Dioxygenase for Production of Useful Amino Acids

Characterization of Bacillus thuringiensis l -Isoleucine Dioxygenase for Production of Useful Amino Acids

4-Hydroxyisoleucine production of recombinant Corynebacterium glutamicum ssp. lactofermentum under optimal corn steep liquor limitation

Structural analysis of enzymes used for bioindustry and bioremediation

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