Search results for: Kuniki Kino

Items from 1 to 20 out of 69 results

article

Ectoine hydroxylase displays selective trans-3-hydroxylation activity towards l-proline

Ryotaro Hara, Takeyuki Nishikawa, Takuya Okuhara, Kento Koketsu, more

Applied Microbiology and Biotechnology > 2019 > 103 > 14 > 5689-5698

l-Hydroxyproline (Hyp) is a valuable intermediate for the synthesis of pharmaceuticals; consequently, a practical process for its production has been in high demand. To date, industrial processes have been developed by using l-Pro hydroxylases. However, a process for the synthesis of trans-3-Hyp has not yet been established, because of the lack of highly selective enzymes that can convert l-Pro to...

article

Isolation and characterization of Gram-negative and Gram-positive bacteria capable of producing piceatannol from resveratrol

Toshiki Furuya, Naoto Imaki, Kosuke Shigei, Masahiko Sai, more

Applied Microbiology and Biotechnology > 2019 > 103 > 14 > 5811-5820

Piceatannol is a valuable natural polyphenol with therapeutic potential in cardiovascular and metabolic disease treatment. In this study, we screened for microorganisms capable of producing piceatannol from resveratrol via regioselective hydroxylation. In the first screening, we isolated microorganisms utilizing resveratrol, phenol, or 4-hydroxyphenylacetic acid as a carbon source for growth. In the...

article

Biotechnological production of vanillin using immobilized enzymes

Toshiki Furuya, Mari Kuroiwa, Kuniki Kino

Journal of Biotechnology > 2017 > 243 > C > 25-28

Vanillin is an important and popular plant flavor, but the amount of this compound available from plant sources is very limited. Biotechnological methods have high potential for vanillin production as an alternative to extraction from plant sources. Here, we report a new approach using immobilized enzymes for the production of vanillin. The recently discovered oxygenase Cso2 has coenzyme-independent...

article

Effective production of Pro–Gly by mutagenesis of l-amino acid ligase

Haruka Kino, Shota Nakajima, Toshinobu Arai, Kuniki Kino

Journal of Bioscience and Bioengineering > 2016 > 122 > 2 > 155-159

l-Amino acid ligase (Lal) catalyzes dipeptide synthesis from unprotected l-amino acids by hydrolysis ATP to ADP. Each Lal displays unique substrate specificity, and many different dipeptides can be synthesized by selecting suitable Lal. We have already successfully synthesized Met–Gly selectively by replacing the Pro85 residues of Lal from Bacillus licheniformis (BL00235). From these results, we deduced...

article

Development of a multi-enzymatic cascade reaction for the synthesis of trans-3-hydroxy-l-proline from l-arginine

Ryotaro Hara, Saki Kitatsuji, Kai Yamagata, Kuniki Kino

Applied Microbiology and Biotechnology > 2016 > 100 > 1 > 243-253

Naturally occurring l-hydroxyproline in its four regio- and stereoisomeric forms has been explored as a possible precursor for pharmaceutical agents, yet the selective synthesis of trans-3-hydroxy-l-proline has not been achieved. Our aim was to develop a novel biocatalytic asymmetric method for the synthesis of trans-3-hydroxy-l-proline. So far, we focused on the rhizobial arginine catabolic pathway:...

article

Enzymatic carboxylation of hydroxystilbenes by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions

Masaru Sato, Nozomu Sakurai, Hideyuki Suzuki, Daisuke Shibata, more

Journal of Molecular Catalysis B: Enzymatic > 2015 > 122 > C > 348-352

We examined 66 aromatics for carboxylation by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions. The enzyme carboxylated resorcinol, catechol, 5-methylresorcinol and three hydroxystilbenes (resveratrol, gnetol, and piceatannol) with high yields. Except for catechol, the structures of these substrates include a 1,3-dihydroxybenzene moiety. Other...

article

Structure of RizA, an L‐amino‐acid ligase from Bacillus subtilis

Wataru Kagawa, Toshinobu Arai, Shun Ishikura, Kuniki Kino, more

Acta Crystallographica Section F > 71 > 9 > 1125 - 1130

RizA is an L‐amino‐acid ligase from Bacillus subtilis that participates in the biosynthesis of rhizocticin, an oligopeptide antibiotic. The substrate‐free form of RizA has been crystallized and the structure was solved at 2.8 Å resolution. The amino‐acid‐binding site appears to be capable of accommodating multiple amino acids, consistent with previous biochemical studies.

article

High-yield production of vanillin from ferulic acid by a coenzyme-independent decarboxylase/oxygenase two-stage process

Toshiki Furuya, Misa Miura, Mari Kuroiwa, Kuniki Kino

New BIOTECHNOLOGY > 2015 > 32 > 3 > 335-339

Vanillin is one of the world's most important flavor and fragrance compounds in foods and cosmetics. Recently, we demonstrated that vanillin could be produced from ferulic acid via 4-vinylguaiacol in a coenzyme-independent manner using the decarboxylase Fdc and the oxygenase Cso2. In this study, we investigated a new two-pot bioprocess for vanillin production using the whole-cell catalyst of Escherichia...

article

Hydroxamate-based colorimetric assay to assess amide bond formation by adenylation domain of nonribosomal peptide synthetases

Ryotaro Hara, Ryohei Suzuki, Kuniki Kino

Analytical Biochemistry > 2015 > 477 > Complete > 89-91

We demonstrated the usefulness of a hydroxamate-based colorimetric assay for predicting amide bond formation (through an aminoacyl-AMP intermediate) by the adenylation domain of nonribosomal peptide synthetases. By using a typical adenylation domain of tyrocidine synthetase (involved in tyrocidine biosynthesis), we confirmed the correlation between the absorbance at 490nm of the l-Trp–hydroxamate–Fe...

article

Alteration of the substrate specificity of cytochrome P450 CYP199A2 by site-directed mutagenesis

Toshiki Furuya, Yoh Shitashima, Kuniki Kino

Journal of Bioscience and Bioengineering > 2015 > 119 > 1 > 47-51

CYP199A2, a member of the cytochrome P450 family, is a monooxygenase that specializes in the oxidation of aromatic carboxylic acids. The crystal structure of CYP199A2 determined by Bell et al. (J. Mol. Biol., 383, 561–574, 2008) suggested that the S97 and S247 residues conferred the substrate specificity on this enzyme through interaction between the hydroxy side chains of these Ser residues and the...

article

Regioselective hydroxylation of aromatic carboxylic acids by cytochrome P450 CYP199A2 and its mutants

Toshiki Furuya, Kuniki Kino

New BIOTECHNOLOGY > 2014 > 31 > Supplement > S80

article

Regioselective synthesis of piceatannol from resveratrol: catalysis by two-component flavin-dependent monooxygenase HpaBC in whole cells

Toshiki Furuya, Kuniki Kino

Tetrahedron Letters > 2014 > 55 > 17 > 2853-2855

Piceatannol, a valuable biologically active stilbene derivative, was efficiently synthesized from resveratrol. Whole-cell catalysis with HpaBC monooxygenase enabled the regioselective hydroxylation of resveratrol to produce 23mM (5.2gL ⁻¹ ) of piceatannol.

article

Identification and characterization of 2-oxoglutarate-dependent dioxygenases catalyzing selective cis-hydroxylation of proline and pipecolinic acid from actinomycetes

Ryotaro Hara, Naoko Uchiumi, Kuniki Kino

Journal of Biotechnology > 2014 > 172 > C > 55-58

Microbial hydroxylases were screened for the capacity to effect direct hydroxylation of proline and pipecolinic acid, based on genomic information. Of the eight candidates screened, 2-oxoglutarate-dependent hydroxylase from Streptosporangium roseum NBRC 3776^T and aspartyl/asparaginyl β-hydroxylase from Catenulispora acidiphila NBRC 102108^T showed both proline and pipecolinic acid hydroxylation activities...

article

Catalytic activity of the two-component flavin-dependent monooxygenase from Pseudomonas aeruginosa toward cinnamic acid derivatives

Toshiki Furuya, Kuniki Kino

Applied Microbiology and Biotechnology > 2014 > 98 > 3 > 1145-1154

4-Hydroxyphenylacetate 3-hydroxylases (HPAHs) of the two-component flavin-dependent monooxygenase family are attractive enzymes that possess the catalytic potential to synthesize valuable ortho-diphenol compounds from simple monophenol compounds. In this study, we investigated the catalytic activity of HPAH from Pseudomonas aeruginosa strain PAO1 toward cinnamic acid derivatives. We prepared Escherichia coli...

article

Biocatalytic production of 5-hydroxy-2-adamantanone by P450cam coupled with NADH regeneration

Toshiki Furuya, Takaaki Kanno, Hiroaki Yamamoto, Norihiro Kimoto, more

Journal of Molecular Catalysis. B, Enzymatic > 2013 > 94 > Complete > 111-118

5-Hydroxy-2-adamantanone is a versatile starting material for the synthesis of various adamantane derivatives. In this study, we investigated the biocatalytic production of 5-hydroxy-2-adamantanone using P450cam monooxygenase coupled with NADH regeneration. We constructed Escherichia coli cells that expressed P450cam and its redox partners, putidaredoxin and putidaredoxin reductase, and cells that...

article

Application of protein N-terminal amidase in enzymatic synthesis of dipeptides containing acidic amino acids specifically at the N-terminus

Toshinobu Arai, Atsushi Noguchi, Eriko Takano, Kuniki Kino

Journal of Bioscience and Bioengineering > 2013 > 115 > 4 > 382-387

Dipeptides exhibit unique physiological functions and physical properties, e.g., l-aspartyl-l-phenylalanine-methyl ester (Asp–Phe–OMe, aspartame) as an artificial sweetener, and functional studies of peptides have been carried out in various fields. Therefore, to establish a manufacturing process for the useful dipeptides, we investigated its enzymatic synthesis by utilizing an l-amino acid ligase...

article

The mycobacterial binuclear iron monooxygenases require a specific chaperonin‐like protein for functional expression in a heterologous host

Toshiki Furuya, Mika Hayashi, Hisashi Semba, Kuniki Kino

The FEBS Journal > 280 > 3 > 817 - 826

The mimABCD gene clusters in Mycobacterium smegmatis strain mc²155 and Mycobacterium goodii strain 12523 encode binuclear iron monooxygenases that oxidize propane and phenol. In this study, we attempted to express each mimABCD gene cluster in a heterologous host. The actinomycetous strain Rhodococcus opacus B‐4, which is phylogenetically close to Mycobacterium, was selected as the host. Each mimABCD...

article

Microbial production of N-acetyl cis-4-hydroxy-l-proline by coexpression of the Rhizobium l-proline cis-4-hydroxylase and the yeast N-acetyltransferase Mpr1

Thi Mai Hoa Bach, Ryotaro Hara, Kuniki Kino, Iwao Ohtsu, more

Applied Microbiology and Biotechnology > 2013 > 97 > 1 > 247-257

The proline analogue cis-4-hydroxy-l-proline (CHOP), which inhibits the biosynthesis of collagen, has been clinically evaluated as an anticancer drug, but its water solubility and low molecular weight limits its therapeutic potential since it is rapidly excreted. In addition, CHOP is too toxic to be practical as an anticancer drug, due primarily to its systematic effects on noncollagen proteins. To...

article

Enhanced synthesis of 5-hydroxy-l-tryptophan through tetrahydropterin regeneration

Ryotaro Hara, Kuniki Kino

AMB Express > 2013 > 3 > 1 > 1-7

5-Hydroxy-l-tryptophan (5-HTP) is a naturally occurring aromatic amino acid present in the seeds of the African plant Griffonia simplicifolia. Although 5-HTP has therapeutic effects in various symptoms, efficient method of producing 5-HTP has not been established. In this study, we developed a novel cofactor regeneration process to achieve enhanced synthesis of 5-HTP by using modified l-phenylalanine...

article

Novel CCK‐dependent vasorelaxing dipeptide, Arg‐Phe, decreases blood pressure and food intake in rodents

Tomomi Kagebayashi, Noriyasu Kontani, Yuko Yamada, Takafumi Mizushige, more

Molecular Nutrition & Food Research > 56 > 9 > 1456 - 1463

ScopeWe found that a dipeptide, Arg‐Phe (RF), had vasorelaxing activity in mesenteric artery isolated from spontaneously hypertensive rats (SHRs) (EC₅₀ = 580 nM). We then investigated its mechanism of action, and elucidated its physiological functions. Methods and resultsVasorelaxing activities of RF‐related peptides were tested. The retro‐sequence dipeptide FR was inactive, suggesting that the RF...

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Search results for: Kuniki Kino

Ectoine hydroxylase displays selective trans-3-hydroxylation activity towards l-proline

Isolation and characterization of Gram-negative and Gram-positive bacteria capable of producing piceatannol from resveratrol

Biotechnological production of vanillin using immobilized enzymes

Effective production of Pro–Gly by mutagenesis of l-amino acid ligase

Development of a multi-enzymatic cascade reaction for the synthesis of trans-3-hydroxy-l-proline from l-arginine

Enzymatic carboxylation of hydroxystilbenes by the γ-resorcylic acid decarboxylase from Rhizobium radiobacter WU-0108 under reverse reaction conditions

Structure of RizA, an L‐amino‐acid ligase from Bacillus subtilis

High-yield production of vanillin from ferulic acid by a coenzyme-independent decarboxylase/oxygenase two-stage process

Hydroxamate-based colorimetric assay to assess amide bond formation by adenylation domain of nonribosomal peptide synthetases

Alteration of the substrate specificity of cytochrome P450 CYP199A2 by site-directed mutagenesis

Regioselective hydroxylation of aromatic carboxylic acids by cytochrome P450 CYP199A2 and its mutants

Regioselective synthesis of piceatannol from resveratrol: catalysis by two-component flavin-dependent monooxygenase HpaBC in whole cells

Identification and characterization of 2-oxoglutarate-dependent dioxygenases catalyzing selective cis-hydroxylation of proline and pipecolinic acid from actinomycetes

Catalytic activity of the two-component flavin-dependent monooxygenase from Pseudomonas aeruginosa toward cinnamic acid derivatives

Biocatalytic production of 5-hydroxy-2-adamantanone by P450cam coupled with NADH regeneration

Application of protein N-terminal amidase in enzymatic synthesis of dipeptides containing acidic amino acids specifically at the N-terminus

The mycobacterial binuclear iron monooxygenases require a specific chaperonin‐like protein for functional expression in a heterologous host

Microbial production of N-acetyl cis-4-hydroxy-l-proline by coexpression of the Rhizobium l-proline cis-4-hydroxylase and the yeast N-acetyltransferase Mpr1

Enhanced synthesis of 5-hydroxy-l-tryptophan through tetrahydropterin regeneration

Novel CCK‐dependent vasorelaxing dipeptide, Arg‐Phe, decreases blood pressure and food intake in rodents

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