Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: a biocatalytic equivalent to the Kolbe–Schmitt reaction
作者： Christiane Wuensch , Johannes Gross , Georg Steinkellner , Andrzej Lyskowski , Karl Gruber
DOI: 10.1039/C3RA47719C
关键词:
摘要: The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense bicarbonate as CO2 source is reported. In contrast to classic Kolbe–Schmitt reaction, biocatalytic equivalent proceeded in a highly regioselective fashion exclusively ortho-position phenolic directing group up 80% conversion. Several enzymes were identified, which displayed remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino-functionalities. Based on crystal structure molecular docking simulations, mechanistic proposal for 2,6-dihydroxybenzoic decarboxylase presented.
rsc.org
sci-hub.se 参考文章(38)
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
Tsuyoshi Matsui, Toyokazu Yoshida, Tomohiro Yoshimura, Toru Nagasawa, Regioselective carboxylation of 1,3-dihydroxybenzene by 2,6-dihydroxybenzoate decarboxylase of Pandoraea sp. 12B-2 Applied Microbiology and Biotechnology. ,vol. 73, pp. 95- 102 ,(2006) , 10.1007/S00253-006-0437-Z
Matthias Boll, Georg Fuchs, Unusual reactions involved in anaerobic metabolism of phenolic compounds. Biological Chemistry. ,vol. 386, pp. 989- 997 ,(2005) , 10.1515/BC.2005.115
J. Liu, X. Zhang, S. Zhou, P. Tao, J. Liu, Purification and Characterization of a 4-Hydroxybenzoate Decarboxylase from Chlamydophila pneumoniae AR39 Current Microbiology. ,vol. 54, pp. 102- 107 ,(2007) , 10.1007/S00284-006-0153-Z
Tsuyoshi Matsui, Toyokazu Yoshida, Toshihisa Hayashi, Toru Nagasawa, Purification, characterization, and gene cloning of 4-hydroxybenzoate decarboxylase of Enterobacter cloacae P240 Archives of Microbiology. ,vol. 186, pp. 21- 29 ,(2006) , 10.1007/S00203-006-0117-5
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
B LUPA, D LYON, M GIBBS, R REEVES, J WIEGEL, Distribution of genes encoding the microbial non-oxidative reversible hydroxyarylic acid decarboxylases/phenol carboxylases Genomics. ,vol. 86, pp. 342- 351 ,(2005) , 10.1016/J.YGENO.2005.05.002
Christiane Wuensch, Nina Schmidt, Johannes Gross, Barbara Grischek, Silvia M. Glueck, Kurt Faber, Pushing the equilibrium of regio-complementary carboxylation of phenols and hydroxystyrene derivatives. Journal of Biotechnology. ,vol. 168, pp. 264- 270 ,(2013) , 10.1016/J.JBIOTEC.2013.07.017
Yuichiro Iwasaki, Kuniki Kino, Hiroyuki Nishide, Kohtaro Kirimura, Regioselective and enzymatic production of γ-resorcylic acid from resorcinol using recombinant Escherichia coli cells expressing a novel decarboxylase gene Biotechnology Letters. ,vol. 29, pp. 819- 822 ,(2007) , 10.1007/S10529-007-9309-6
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