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M. Nakanishi, K. Matsuura, Hiroyuki Kaibe, N. Tanaka, T. Nonaka, Y. Mitsui, A. Harã (1997)
Switch of Coenzyme Specificity of Mouse Lung Carbonyl Reductase by Substitution of Threonine 38 with Aspartic Acid*The Journal of Biological Chemistry, 272
W. Griffin, G. Lin (2000)
Chemotaxonomy and geographical distribution of tropane alkaloids.Phytochemistry, 53 6
Ken-ichi Suzuki, Yasuyuki Yamada, Takashi Hashimoto (1999)
Expression of Atropa belladonna putrescine N-methyltransferase gene in root pericycle.Plant & cell physiology, 40 3
K. Nakajima, H. Kato, J. Oda, Y. Yamada, T. Hashimoto (1999)
Site-directed Mutagenesis of Putative Substrate-binding Residues Reveals a Mechanism Controlling the Different Stereospecificities of Two Tropinone Reductases*The Journal of Biological Chemistry, 274
R. Keiner, B. Dräger (2000)
Calystegine distribution in potato (Solanum tuberosum) tubers and plantsPlant Science, 150
B. Persson, M. Krook, H. Jörnvall (1991)
Characteristics of short-chain alcohol dehydrogenases and related enzymes.European journal of biochemistry, 200 2
K. Nakajima, Y. Oshita, M. Kaya, Y. Yamada, T. Hashimoto (1999)
Structures and expression patterns of two tropinone reductase genes from Hyoscyamus niger.Bioscience, biotechnology, and biochemistry, 63 10
Y. Scholl, D. Höke, B. Dräger (2001)
Calystegines in Calystegia sepium derive from the tropane alkaloid pathway.Phytochemistry, 58 6
K. Nakajima, T. Hashimoto, Yasuyuki Yamada (1993)
Two tropinone reductases with different stereospecificities are short-chain dehydrogenases evolved from a common ancestor.Proceedings of the National Academy of Sciences of the United States of America, 90 20
B. Dräger, C. Funck, A. Höhler, G. Mrachatz, A. Nahrstedt, A. Portsteffen, A. Schaal, R. Schmidt (1994)
Calystegines as a new group of tropane alkaloids in SolanaceaePlant Cell, Tissue and Organ Culture, 38
B. Dräger, A. Schaal (1994)
Tropinone reduction in Atropa belladonna root culturesPhytochemistry, 35
J. Brandstädter, C. Roßbach, K. Theres (1993)
The pattern of histone H4 expression in the tomato shoot apex changes during developmentPlanta, 192
K. Nakajima, A. Yamashita, Hiroyuki Akama, T. Nakatsu, H. Kato, T. Hashimoto, J. Oda, Y. Yamada (1998)
Crystal structures of two tropinone reductases: different reaction stereospecificities in the same protein fold.Proceedings of the National Academy of Sciences of the United States of America, 95 9
N. Tanaka, T. Nonaka, M. Nakanishi, Y. Deyashiki, A. Harã, Y. Mitsui (1997)
Crystal structure of the ternary complex of mouse lung carbonyl reductase at 1.8 A resolution: the structural origin of coenzyme specificity in the short-chain dehydrogenase/reductase family.Structure, 4 1
H. Jörnvall, B. Persson, M. Krook, S. Atrian, R. Gonzàlez-Duarte, J. Jeffery, D. Ghosh (1995)
Short-chain dehydrogenases/reductases (SDR).Biochemistry, 34 18
B. Persson, M. Krook, H. Jörnvall (1995)
Short-chain dehydrogenases/reductases.Advances in experimental medicine and biology, 372
A. Portsteffen, B. Draeger, A. Nahrstedt (1992)
Two tropinone reducing enzymes from Datura stramonium transformed root culturesPhytochemistry, 31
C. Reinbothe, A. Tewes, M. Luckner, S. Reinbothe (1992)
Differential gene expression during somatic embryogenesis in Digitalis Ianata analyzed by in vivo and in vitro protein synthesisPlant Journal, 2
A. Portsteffen, B. Dräger, A. Nahrstedt (1994)
The reduction of tropinone in Datura stramonium root cultures by two specific reductases.Phytochemistry, 37 2
B. Dräger, A. Almsick, G. Mrachatz (1995)
Distribution of Calystegines in Several SolanaceaePlanta Medica, 61
M. Nakanishi, M. Kakumoto, K. Matsuura, Y. Deyashiki, N. Tanaka, T. Nonaka, Y. Mitsui, A. Harã (1996)
Involvement of two basic residues (Lys-17 and Arg-39) of mouse lung carbonyl reductase in NADP(H)-binding and fatty acid activation: site-directed mutagenesis and kinetic analyses.Journal of biochemistry, 120 2
M. Bradford (1976)
A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.Analytical biochemistry, 72
K. Nakajima, Y. Oshita, Y. Yamada, T. Hashimoto (1999)
Insight into the molecular evolution of two tropinone reductases.Bioscience, biotechnology, and biochemistry, 63 10
B. Dräger, T. Hashimoto, Yasuyuki Yamada (1988)
Purification and Characterization of Pseudotropine Forming Tropinone Reductase from Hyoscyamus niger Root CulturesAgricultural and biological chemistry, 52
Atsuko Yamashita, Hiroaki Kato, Soichi Wakatsuki, Takashi Tomizaki, T. Nakatsu, K. Nakajima, Takashi Hashimoto, Yasuyuki Yamada, Jun'ichi Oda, Jun'ichi Oda (1999)
Structure of tropinone reductase-II complexed with NADP+ and pseudotropine at 1.9 A resolution: implication for stereospecific substrate binding and catalysis.Biochemistry, 38 24
L. Witte, K. Müller, H. Arfmann (1987)
Investigation of the Alkaloid Pattern of Datura innoxia Plants by Capillary Gas-Liquid-Chromatography-Mass SpectrometryPlanta Medica, 53
N. Asano, R. Nash, R. Molyneux, G. Fleet (2000)
Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic applicationTetrahedron-asymmetry, 11
K. Nakajima, T. Hashimoto, Y. Yamada (1993)
cDNA Encoding Tropinone Reductase-II from Hyoscyamus niger, 103
Takashi Hashimoto, K. Nakajima, Godelieve Ongena, Yasuyuki Yamada (1992)
Two Tropinone Reductases with Distinct Stereospecificities from Cultured Roots of Hyoscyamus niger.Plant physiology, 100 2
Zhuo Chen, J. Jiang, Z. Lin, William Lee, M. Baker, Simon Chang (1993)
Site-specific mutagenesis of Drosophila alcohol dehydrogenase: evidence for involvement of tyrosine-152 and lysine-156 in catalysis.Biochemistry, 32 13
Ken‐ichi Suzuki, D. Yun, Xiao-Ya Chen, Yasuyuki Yamada, T. Hashimoto (1999)
An Atropa belladonna hyoscyamine 6β-hydroxylase gene is differentially expressed in the root pericycle and anthersPlant Molecular Biology, 40
A. Goldmann, M. Milat, P. Ducrot, J. Lallemand, M. Maille, A. Lepingle, Isabelle Charpin, D. Tepfer (1990)
Tropane derivatives from Calystegia sepiumPhytochemistry, 29
Calystegines are nortropane alkaloids that are found in Solanaceae containing the classical tropane alkaloids hyoscyamine and scopolamine, and in other Solanaceae such as potato, Solanum tuberosum (L.). Calystegines are assumed to derive from the classical tropane alkaloid pathway. We isolated a cDNA from S. tuberosum with high homology to the pseudotropine-forming tropinone reductase (TRII), which presents as the first putative metabolite specific to calystegines. The equivalent amino acid sequence shows typical motifs of a short-chain dehydrogenase (SDR). The recombinant TRII protein expressed in Escherichia coli catalyzes pseudotropine formation from tropinone with a K m value, a pH optimum, substrate and co-substrate preferences similar to those reported for the TRII enzymes from other Solanaceae species. The gene is expressed in roots, tubers and aerial parts of potato. The distribution of the TRII transcript in comparison with the calystegine concentrations in the tissues suggests transport of calystegines or their precursors between potato organs.
Plant Molecular Biology – Springer Journals
Published: Oct 13, 2004
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