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

作者: Masaru Sato , Nozomu Sakurai , Hideyuki Suzuki , Daisuke Shibata , Kuniki Kino

DOI: 10.1016/J.MOLCATB.2015.10.006

关键词: Organic chemistryBenzoic acidCarboxylationResorcinolEnzymeResveratrolChemistryCatecholPiceatannolMoiety

摘要: Abstract 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, piceatannol) with high yields. Except structures of these substrates include a 1,3-dihydroxybenzene moiety. Other compounds gave no products. products resveratrol gnetol were 2,6-dihydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoic 2,6-dihydroxy-4-[(E)-2-(2,6-dihydroxyphenyl)ethenyl]benzoic acid, respectively, as determined mass spectrometry nuclear magnetic resonance analyses. Kinetic analyses reactions indicated that are better than resorcinol or catechol.

参考文章(14)
Kohtaro Kirimura, Satomi Yanaso, Sachiyo Kosaka, Keiko Koyama, Takasumi Hattori, Yoshitaka Ishii, Production ofp-Aminosalicylic Acid through Enzymatic Kolbe–Schmitt Reaction Catalyzed by Reversible Salicylic Acid Decarboxylase Chemistry Letters. ,vol. 40, pp. 206- 208 ,(2011) , 10.1246/CL.2011.206
Christiane Wuensch, Johannes Gross, Georg Steinkellner, Andrzej Lyskowski, Karl Gruber, Silvia M. Glueck, Kurt Faber, Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: a biocatalytic equivalent to the Kolbe–Schmitt reaction RSC Advances. ,vol. 4, pp. 9673- 9679 ,(2014) , 10.1039/C3RA47719C
Toyokazu Yoshida, Yuki Inami, Tsuyoshi Matsui, Toru Nagasawa, Regioselective carboxylation of catechol by 3,4-dihydroxybenzoate decarboxylase of Enterobacter cloacae P Biotechnology Letters. ,vol. 32, pp. 701- 705 ,(2010) , 10.1007/S10529-010-0210-3
Kohtaro Kirimura, Hiroaki Gunji, Rumiko Wakayama, Takasumi Hattori, Yoshitaka Ishii, Enzymatic Kolbe–Schmitt reaction to form salicylic acid from phenol: Enzymatic characterization and gene identification of a novel enzyme, Trichosporon moniliiforme salicylic acid decarboxylase Biochemical and Biophysical Research Communications. ,vol. 394, pp. 279- 284 ,(2010) , 10.1016/J.BBRC.2010.02.154
Christiane Wuensch, Silvia M. Glueck, Johannes Gross, Dominik Koszelewski, Markus Schober, Kurt Faber, Regioselective enzymatic carboxylation of phenols and hydroxystyrene derivatives. Organic Letters. ,vol. 14, pp. 1974- 1977 ,(2012) , 10.1021/OL300385K
Alan S. Lindsey, Harold Jeskey, The Kolbe-Schmitt Reaction Chemical Reviews. ,vol. 57, pp. 583- 620 ,(1957) , 10.1021/CR50016A001
Toyokazu YOSHIDA, Kohei FUJITA, Toru NAGASAWA, Novel reversible indole-3-carboxylate decarboxylase catalyzing nonoxidative decarboxylation Bioscience, Biotechnology, and Biochemistry. ,vol. 66, pp. 2388- 2394 ,(2002) , 10.1271/BBB.66.2388
Hironori Omura, Marco Wieser, Toru Nagasawa, PYRROLE-2-CARBOXYLATE DECARBOXYLASE FROM BACILLUS MEGATERIUM PYR2910, AN ORGANIC-ACID-REQUIRING ENZYME FEBS Journal. ,vol. 253, pp. 480- 484 ,(1998) , 10.1046/J.1432-1327.1998.2530480.X
Masaru Goto, Hideyuki Hayashi, Ikuko Miyahara, Ken Hirotsu, Masahiro Yoshida, Tadao Oikawa, Crystal Structures of Nonoxidative Zinc-dependent 2,6-Dihydroxybenzoate (γ-Resorcylate) Decarboxylase from Rhizobium sp. Strain MTP-10005 Journal of Biological Chemistry. ,vol. 281, pp. 34365- 34373 ,(2006) , 10.1074/JBC.M607270200
A. Grosdidier, V. Zoete, O. Michielin, SwissDock, a protein-small molecule docking web service based on EADock DSS Nucleic Acids Research. ,vol. 39, pp. 270- 277 ,(2011) , 10.1093/NAR/GKR366