北海道大学 大学院工学研究院 / 大学院総合化学院 応用生物化学研究室

Article2009

Prof. DAIRI, Before 2009

71 C. Nakano, T. Hoshino, T. Sato, T. Toyomasu, T. Dairi, and T. Sassa, Substrate Specificity of the CYC2 Enzyme from Kitasatospora griseola: Production of Sclarene, Biformene and Novel Bicyclic Diterpenes by the Enzymatic Reactions of Labdane- and Halimane-type Diterpene Diphosphates. Tetrahedron Lett., 51, 125-128 (2009).

70 M. Hashimoto, Y. Higuchi, S. Takahashi, H. Osada, T. Sakaki, T. Toyomasu, T. Sassa, N. Kato, and T. Dairi, Functional Analyses of Cytochrome P450 Genes Responsible for the Early Steps of Brassicicene C Biosynthesis. Bioorg. Med. Chem. Lett., 19, 5640 -5643 (2009).

69 T. Toyomasu, A. Kaneko, T. Tokiwano, Y. Kanno, Y. Kanno, R. Niida, S. Miura, T. Nishioka, C. Ikeda, W. Mitsuhashi, T. Dairi, T. Kawano, H. Oikawa, N. Kato, and T. Sassa, Biosynthetic Gene-based Secondary Metabolites Screening: A New Diterpene, Methyl Phomopsenonate from the Fungus Phompsis amygdale. J. Org. Chem., 74, 1541-1548 (2009).

68 T. Hiratsuka, N. Itoh, H. Seto, and T. Dairi, Enzymatic Properties of Futalosine Hydrolase, an Enzyme Essential for a Newly Identified Menaquinone Biosynthetic Pathway. Biosci. Biotech. Biochem., 73, 1137-1141 (2009).

67 A. Minami, N. Tajima, Y. Higuchi, T. Toyomasu, T. Sassa, N. Kato, and T. Dairi, Identification and Functional Analysis of Brassicicene C Biosynthetic Gene Cluster in Alternaria brassicicola. Bioorg. Med. Chem. Lett., 19, 870–874 (2009).

66 T. Hiratsuka, K. Furihata, J. Ishikawa, H. Yamashita, N. Itoh, H. Seto, and T. Dairi, An Alternative Menaquinone Biosynthetic Pathway Operating in Microorganisms, Science, 321, 1670-1673 (2008). 

65 Y. Hayashi, N. Matsuura, H. Toshima, N. Itoh, J. Ishikawa, Y. Mikami, and T. Dairi. Cloning of the Gene Cluster Responsible for the Biosynthesis of Brasilicardin A, a Unique Diterpenoid. J. Antibiot., 61, 164-174 (2008).

64 T. Toyomasu, R. Niida, H. Kenmoku, Y. Kanno, S. Miura, C. Nakano, Y. Shiono, W. Mitsuhashi, H. Toshima, H. Oikawa, T. Hoshino, T. Dairi, N. Kato, and T. Sassa, Identification of Diterpene Biosynthetic Gene Clusters and Functional Analysis of Labdane-Related Diterpene Cyclases in Phomopsis amygdale. Biosci. Biotech. Biochem., 72, 1038-1047 (2008).

63 H. Seto, Y. Jinnai, T. Hiratsuka, M. Fukawa, K. Furihata, N. Itoh, and T. Dairi. Studies on a New Biosynthetic Pathway for Menaquinone. J. Am. Chem. Soc., 130, 5614-5615 (2008).

62 Y. Hayashi, T. Toyomasu, Y. Hirose, Y. Onodera, W. Mitsuhashi, H. Yamane, T. Sassa, and T. Dairi, Comparison of the Enzymatic Properties of ent-Copalyl Diphosphate Synthases in the Biosynthesis of Phytoalexins and Gibberellins in Rice, Biosci. Biotech. Biochem.,72, 523-530 (2008).

61 Y. Makino, T. Dairi, and N. Itoh, Engineering the Phenylacetaldehyde Reductase Mutant for Improved Substrate Conversion in the Presence of Concentrated 2-Propanol, Appl. Microbiol. Biotechnol., 77, 833-843 (2007).

60 Y. Hayashi, H. Onaka, N. Itoh, H. Seto, and T. Dairi, Cloning of the Gene Cluster Responsible for Biosynthesis of KS-505a (longestin), a Unique Tetraterpenoid, Biosci. Biotech. Biochem., 71, 3072-3081 (2007).

59 K. Motohashi, R. Ueno, M. Sue, K. Furihata, T. Matsumoto, T. Dairi, S. Omura, and H. Seto, Studies on Terpenoids Produced by Actinomycetes: Oxaloterpins A, B, C, D, and E, Diterpenes from Streptomyces sp. KO-3988, J. Nat. Prod. 70, 1712-1717 (2007).

58 C. Ikeda, Y. Hayashi, N. Itoh, H. Seto, and T. Dairi, Functional Analysis of Eubacterial ent-Copalyl Diphosphate Synthase and Pimara-9(11),15-diene Synthase with Unique Primary Sequences. J. Biochem., 141, 37-45 (2007).

57 T. Toyomasu, M. Tsukahara, A. Kaneko, R. Niida, W. Mitsuhashi, T. Dairi, N. Kato, and T. Sassa, Fusicoccins are Biosynthesized by an Unusual Chimera Diterpene Synthase in Fungi, Proc. Natl. Acad. Sci. U S A, 104, No. 9, 3084-3088 (2007).

56 X. Wu, P. M. Flatt, O. Schlörke, A. Zeeck, T. Dairi, and T. Mahmud, A Comparative Analysis of the Sugar Phosphate Cyclase Superfamily Involved in Primary and Secondary Metabolism. ChemBioChem., 8, Issiue 2, 239-248 (2007).

55 T. Kawasaki, Y. Hayashi, T. Kuzuyama, K. Furihata, N. Itoh, H. Seto, and T. Dairi, Biosynthesis of a Natural Polyketide-isoprenoid Hybrid Compound Furaquinocin A: Identification and Heterologous Expression of the Gene Cluster. J. Bacteriol., 188, 1236-1244 (2006).

54 K. Inoue, Y. Makino, T. Dairi, and N. Itoh, Gene Cloning and Expression of Leifsonia Alcohol Dehydrogenase (LSADH) Involved in Asymmetric Hydrogen-Transfer Bioreduction to Produce (R)-Form Chiral Alcohols. Biosci. Biotech. Biochem., 70, 418-426 (2006).

53 C. Nakano, T. Okamura, T. Sato, T. Dairi, and T. Hoshino, Mycobacterium tuberculosis H37Rv 3377c Encodes the Diterpene Cyclase for Producing Halimane Skeleton. Chem. Commun., Issue 8, 1016–1018 (2005).

52 K. J. Puan, H. Wang, T. Dairi, T. Kuzuyama, and C. T. Morita, fldA is an Essential Gene Required in the 2-C-Methyl-D-erythritol 4-phosphate Pathway for Isoprenoid Biosynthesis. FEBS Lett. 579, 3802-3806 (2005).

51 Y. Makino, K. Inoue, T. Dairi, and N. Itoh, Engineering of Phenylacetaldehyde Reductase for Efficient Substrate Conversion in Concentrated 2-Propanol. Appl. Environ. Microbiol., 71, 4713–4720 (2005).

50 T. Kuzuyama, T. Dairi, H. Yamashita, Y. Shoji, and H. Seto, Heterologous Mevalonate Production in Streptomyces lividans TK23, Biosci. Biotech. Biochem., 68, 931-934 (2004).

49 T. Nakano, K. Miyake, H. Endo, T. Dairi, T. Mizukami, and R. Katsumata, Identification and Cloning of the Gene Involved in the Final Step of Chlortetracycline Biosynthesis in Streptomyces aureofaciens. Biosci. Biotech. Biochem., 68, 1345-1352 (2004).

48 N. Itoh, H. Asako, K. Banno, Y. Makino, M. Shinohara, T. Dairi, R. Wakita, and M. Shimizu, Purification and Characterization of NADPH-Dependent Aldo-keto Reductase Specific for Beta-keto Esters from Penicillium citrinum, and Production of Methyl (S)-4-bromo-3-hydroxybutyrate. Appl. Microbiol. Biotechnol. 66, 53-62 (2004).

47 T. Kawasaki, T. Kuzuyama, Y. Kuwamori, N. Matsuura, N. Itoh, K. Furihata, H. Seto, and T. Dairi, Presence of Copalyl Diphosphate Synthase Gene in an Actinomycete Possessing the Mevalonate Pathway. J. Antibiot. 57, 739-747 (2004).

46 T. Kawasaki, T. Kuzuyama, K. Furihata, N. Itoh, H. Seto, and T. Dairi, A Relationship between the Mevalonate Pathway and Isoprenoid Production in Actinomycetes, J. Antibiot., 56, 957-966 (2003).

45 T. Kawasaki, Y. Hamano, T. Kuzuyama, N. Itoh, H. Seto, and T. Dairi, Interconversion of the Product Specificity of Type I Eubacterial Farnesyl Diphosphate Synthase and Geranylgeranyl Diphosphate Synthase through One Amino Acid Substitution, J. Biochem. 133, 83-91 (2003).

44 J. Q. Liu, T. Dairi, N. Itoh, M. Kataoka, and S. Shimizu, A Novel Enzyme, D-3-Hydroxyaspartate Aldolase from Paracoccus denitrificans IFO 13301: Purification, Characterization, and Gene Cloning. Appl. Microbiol. Biotechnol. 62, 53-60 (2003).

43 T. Eguchi, Y. Dekishima, Y. Hamano, T. Dairi, H. Seto, and K. Kakinuma, A New Approach for the Investigation of Isoprenoid Biosynthesis Featuring Pathway Switching, Deuterium Hyperlabeling, and 1H NMR Spectroscopy. The Reaction Mechanism of a Novel Streptomyces Diterpene Cyclase, J. Org. Chem. 68, 5433 - 5438 (2003).

42 Y. Hamano, T. Dairi, M. Yamamoto, T. Kuzuyama, N. Itoh, and H. Seto, Growth Phase Dependent Expression of the Mevalonate Pathway in a Terpenoid Antibiotic-producing Streptomyces Strain, Biosci. Biotech. Biochem., 66, 808-819 (2002).

41 T. Kawanami, M. Miyakoshi, T. Dairi, and N. Itoh, Reaction Mechanism of the Co2+-Activated Multifunctional Bromoperoxidase-Esterase from Pseudomonas putida IF-3, Arch. Biochem. Biophys., 398, 94-100 (2002).

40 N. Itoh, M. Matuda, M. Mabuchi, T. Dairi, and J. Wang, Chiral Alcohol Production by NADH-dependent Phenylacetaldehyde Reductase Coupled with in situ Regeneration of NADH, Eur. J. Biochem., 269, 2394-2402 (2002).

39 Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, H. Seto, and T. Dairi, Functional Analysis of Eubacterial Diterpene Cyclases Responsible for Biosynthesis of a Diterpene Antibiotic Terpentecin, J. Biol. Chem., 277, 37098-37104 (2002).

38 T. Kuzuyama, S. Takahashi, T. Dairi, and H. Seto, Detection of the mevalonate pathway in Streptomyces species using the 3-hydroxy-3-methylglutaryl coenzyme A reductase gene, J. Antibiot. 55, 919-923 (2002).

37 N. Itoh, T. Kawanami, J. Q. Liu, T. Dairi, M. Miyakoshi, C. Nitta, and Y. Kimoto, Cloning and Biochemical Characterization of Co2+-Activated Bromoperoxidase-esterase (Perhydrolase) from Pseudomonas putida, Biochimica. Biophysica. Acta., 1545, 53-66 (2001).

36 Y. Hamano, T. Dairi, M. Yamamoto, T., Kawasaki, K., Kaneda, T. Kuzuyama, N. Itoh, and H. Seto, Cloning of a Gene Cluster Encoding Enzymes Responsible for the Mevalonate Pathway from a Terpenoid-antibiotic-producing Streptomyces strain, Biosci. Biotech. Biochem., 65, 1627-1635 (2001).

35 T. Dairi, Y. Hamano, T. Kuzuyama, N. Itoh, K. Furihata, and H. Seto, Eubacterial Diterpene Cyclase Genes Essential for Production of Isoprenoid Antibiotic Terpentecin, J. Bacteriol., 183, 6085-6094 (2001).

34 J. Q. Liu, M. Odani, T. Yasuoka, T. Dairi, N. Itoh, M. Kataoka, S. Shimizu, and H. Yamada, Gene Cloning and Overproduction of Low-specificity D-Threonine Aldolase from Alcaligenes xylosoxidans and its Application for Production of a Key Intermediate for Parkinsonism Drug, Appl. Microbiol. Biotechnol., 54, 44-51 (2000).

33 M. Takagi, T. Kuzuyama, K. Kaneda, H. Watanabe, T. Dairi, and H. Seto, Studies on the Nonmevalonate Pathway: Formation of 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate from 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol, Tetrahedron Lett., 41, 3395-3398 (2000).

32 T. Kuzuyama, M. Takagi, K. Kaneda, H. Watanabe, T. Dairi, and H. Seto, Studies on the Nonmevalonate Pathway: Conversion of 4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol to its 2-Phospho Derivative by 4-(Cytidine 5'-diphospho)-2-C-methyl-D-erythritol Kinase, Tetrahedron Lett., 41, 2925-2928 (2000).

31 T. Kuzuyama, M. Takagi, K. Kaneda, T. Dairi, and H. Seto, Formation of 4-(Cytidine 5'-iphospho)-2-C-methyl-D-erythritol from 2-C-Methyl-D-erythritol 4-phosphate by 2-C-Methyl-D-erythritol 4-phosphate Cytidylyltransferase, A New Enzyme in the Nonmevalonate Pathway, Tetrahedron Lett., 41, 703-706 (2000).

30 T. Dairi, Y. Motohira, T. Kuzuyama, S. Takahashi, N. Itoh and H. Seto, Cloning of the Gene Encoding 3-Hydroxy-3-Methylglutaryl Coenzyme A Reductase from Terpenoid Antibiotics-Producing Stereptomyces Strains, Mol. Gen. Genet., 262, 957-964 (2000).

29 T. Dairi, Y. Hamano, T. Furumai, and T. Oki, Development of a Self-cloning System for Actinomadura verrucosospora and Identification of Polyketide Synthase Genes Essential for Production of the Angucyclic Antibiotic Pradimicin, Appl. Environ. Microbiol., 65, 2703-2709 (1999).

28 J. Q. Liu, M. Odani, T. Dairi, N. Itoh, S. Shimizu, and H. Yamada, A New Route to L-Threo-3-[4-(methylthio)phenylserine], a Key Intermediate for the Synthesis of Antibiotics: Recombinant Low-specificity D-Threonine Aldolase-catalyzed Stereospecific Resolution, Appl. Microbiol. Biotechnol., 51, 586-591 (1999).

27 J. C. Wang, M. Sakakibara, J.Q. Liu, T. Dairi, and N. Itoh, Cloning, Sequence Analysis, and Expression in Escerichia coli of the Gene Encoding Phenylacetaldehyde Reductase from Styrene-assimilating Corynebacterium sp. Strain ST-10, Appl. Microbiol. Biotechnol., 52, 386-392 (1999).

26 S. Matsumoto, H. Yukitake, N. Ohara, T. Dairi, H. Kanbara, and T. Yamada, Shotgun Cloning and Characterization of the Thymidylate Synthase-Encoding Gene from Mycobacterium bovis BCG, Microbiol. Immunol., 42, 15-21 (1998).

25 J. Q. Liu, S. Ito, T. Dairi, N. Itoh, S. Shimizu, and H. Yamada, Low-specificity L-Threonine Aldolase of Pseudomonas sp. NCIMB 10558: Purification, Characterization and its Application to Beta-hydroxy-alpha-amino Acid Synthesis, Appl. Microbiol. Biotechnol., 49, 702-708 (1998).

24 J. Q. Liu, S. Ito, T. Dairi, N. Itoh, M. Kataoka, S. Shimizu, and H. Yamada, Gene Cloning, Nucleotide Sequencing, and Purification and Characterization of the Low-specificity L-Threonine Aldolase from Pseudomonas sp. Strain NCIMB10558, Appl. Environ. Microbiol., 64, 549-554 (1998).

23 J. Q. Liu, T. Dairi, N. Itoh, M. Kataoka, S. Shimizu, and H. Yamada, Gene Cloning, Biochemical Characterization and Physiological Role of a Thermostable Low-specificity L-Threonine Aldolase from Escherichia coli, Eur. J. Biochem., 254, 220-226 (1998).

22 J. Q. Liu, T. Dairi, N. Itoh, M. Kataoka, S. Shimizu, and H. Yamada, A Novel Metal-activated Pyridoxal Enzyme with a Unique Primary Structure, Low Specificity D-Threonine Aldolase from Arthrobacter sp. Strain DK-38. Molecular Cloning and Cofactor Characterization, J. Biol. Chem., 273, 16678-16685 (1998).

21 K. L. Britton, H. F. Rogers, Y. Asano, T. Dairi, Y. Kato, T. J. Stillman, and D. W. Rice, Crystallization of Arthrobacter sp. Strain 1C N-(1-D-Carboxyethyl)-L-norvaline Dehydrogenase and its Complex with NAD+, Acta Cryst., D54, 124-126 (1998).

20 T. Dairi, Y. Hamano, Y. Igarashi, T. Furumai, and T. Oki, Protoplasting and Regeneration of Strains Belonging to the Genus Actinomadura, Actinomycetol., 11, 1-5 (1997).

19 J. Q. Liu, T. Dairi, M. Kataoka, S. Shimizu, and H. Yamada, L-allo-Threonine Aldolase from Aeromonas jandaei DK-39: Gene Cloning, Nucleotide Sequencing, and Identification of the Pyridoxal 5'-Phosphate-binding Lysine Residue by Site-directed Mutagenesis, J. Bacteriol., 179, 3555-3560 (1997).

18 J. Q. Liu, S. Nagata, T. Dairi, H. Misono, S. Shimizu, and H. Yamada, The GLY1 Gene of Saccharomyces cerevisiae Encodes a Low Specific L-Threonine Aldolase that Catalyzes Cleavage of L-Threonine and L-allo-Threonine to Glycine: Expression of the Gene in Escherichia coli and Purification and Characterization of the Enzyme, Eur. J. Biochem., 245, 289-293 (1997).

17 T. Dairi, Y. Hamano, Y. Igarashi, T. Furumai, and T. Oki, Cloning and Nucleotide Sequence of the Putative Polyketide Synthase Genes for Pradimicin Biosynthesis from Actinomadura hibisca, Biosci. Biotech. Biochem., 61, 1445-1453 (1997).

16 Y. Asano, H. Ito, T. Dairi, and Y. Kato, An Alkaline D-Stereospecific Endopeptidase with β-Lactamase Activity from Bacillus cereus, J. Biol. Chem., 271, 30256-30262 (1996).

15 K. Nishinaga, M. Murakami, T. Matsunaga, Y. Yokota, H. Saito, T. Dairi, and T. Oki, Electrophoretic Fractionation of Ganoderm licidium Extract under Non-denatured Polyacrylamide Gel, J. Traditional Medicines, 13, 504-505 (1996).

14 T. Dairi, T. Nakano, K. Aisaka, R. Katsumata, and M. Hasegawa, Cloning and Nucleotide Sequence of the Gene Responsible for Chlorination of Tetracycline, Biosci. Biotech. Biochem., 59, 1099-1106 (1995).

13 T. Dairi, T. Nakano, T. Mizukami, K. Aisaka, M. Hasegawa and R. Katsumata, Conserved Organization of Genes for Biosynthesis of Chlortetracycline in Streptomyces Strains, Biosci. Biotech. Biochem., 59, 1360-1361 (1995).

12 T. Dairi and Y. Asano, Cloning, Nucleotide Sequencing, and Expression of an Opin Dehydrogenase Gene from Arthrobacter sp. strain 1C, Appl. Environ. Microbiol., 61, 3169-3171 (1995).

11 T. Dairi, K. Aisaka, R. Katsumata and M. Hasegawa, A Self-defense Gene Homologous to Tetracycline Effluxing Gene Essential for Antibiotic Production in Streptomyces aureofaciens, Biosci. Biotech. Biochem., 59, 1835-1841 (1995).

10 Y. Yamada, T. Dairi, Y. Ohno, X.-L. Huang and Y. Asano, Nucleotide Sequencing of Phenylalanine Dehydrogenase Gene from Bacillus badius IAM11059, Biosci. Biotech. Biochem., 59, 1994-1995 (1995).

9 T. Kuzuyama, T. Seki, T. Dairi, T. Hidaka, and H. Seto, Nucleotide Sequence of Fortimicin KL1, Methyltransferase Gene Isolated from Micromonospora olivasterospora and Comparison of its Deduced Amino Acid Sequence with Those of Methyltransferases Involved in the Biosynthesis of Bialaphos and Fosfomycin, J. Antibiot., 48, 1191-1193 (1995).

8 T. Ohta, T. Dairi, and M. Hasegawa, Characterization of Two Different Types of Resistance Genes among Producers of Fortimicin-Group Antibiotics, J. Gen. Microbiol., 139, 591-599 (1993).

7 T. Ohta, T. Dairi, E. Hashimoto, and M. Hasegawa, Use of a Heterologous Gene for Molecular Breeding of Actinomycetes Producing Structurally Related Antibiotics: Self-defense Genes of Producers of Fortimicin-A (Astromicin)-group Antibiotics, Actinomycetol., 7, 145-155 (1993).

6 T. Dairi, K. Yamaguchi, and M. Hasegawa, N-Formimidoyl Fortimicin A Synthase, a Unique Oxidase Involved in Fortimicin A Biosynthesis: Purification, Characterization and Gene Cloning, Mol. Gen. Genet., 236, 49-59 (1992).

5 T. Dairi, T. Ohta, E. Hashimoto, and M. Hasegawa, Self Cloning in Micromonospora olivasterospora of fms Genes for Fortimicin A (Astromicin) Biosynthesis, Mol. Gen. Genet., 232, 262-270 (1992).

4 T. Dairi, T. Ohta, E. Hashimoto, and M. Hasegawa, Organization and Nature of Fortimicin A (Astromicin) Biosynthetic Genes Studied Using a Cosmid Library of Micromonospora olivasterospora DNA, Mol. Gen. Genet., 236, 39-48 (1992).

3 M. Hasegawa, T. Dairi, T. Ohta, and E. Hashimoto, A Novel, Highly Efficient Gene-Cloning System for Micromonospora Strains, J. Bacteriol., 173, 7004-7011 (1991).

2 T. Dairi and M. Hasegawa, Common Biosynthetic Feature of Fortimicin-Group Antibiotics, J. Antibiot., 42, 934-943 (1989).

1 T. Dairi, K. Inokuchi, T. Mizuno, and S. Mizushima, Positive Control of Transcription Initiation in Escherichia coli, J. Mol. Biol., 184, 1-6 (1985).