404875-20-3Relevant academic research and scientific papers
Biphenyl dioxygenase-catalysed cis-dihydroxylation of tricyclic azaarenes: Chemoenzymatic synthesis of arene oxide metabolites and furoquinoline alkaloids
Boyd, Derek R.,Sharma, Narain D.,Carroll, Jonathan G.,Loke, Pui L.,O'Dowd, Colin R.,Allen, Christopher C. R.
, p. 10944 - 10955 (2013/09/02)
Biotransformation of acridine, dictamnine and 4-chlorofuro[2,3-b]quinolone, using whole cells of Sphingomonas yanoikuyae B8/36, yielded five enantiopure cyclic cis-dihydrodiols, from biphenyl dioxygenase-catalysed dihydroxylation of the carbocyclic rings.
Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes.
Shindo,Ohnishi,Chun,Takahashi,Hayashi,Saito,Iguchi,Furukawa,Harayama,Horinouchi,Misawa
, p. 2472 - 2481 (2007/10/03)
Bioconversion (biotransformation) experiments on arenes (aromatic compounds), including various tricyclic fused aromatic compounds such as fluorene, dibenzofuran, dibenzothiophene, carbazole, acridene, and phenanthridine, were done using the cells of Escherichia coli transformants expressing several arene dioxygenase genes. E. coli carrying the phenanthrene dioxygenase (phdABCD) genes derived from the marine bacterium Nocardioides sp. strain KP7 converted all of these tricyclic aromatic compounds, while E. coli carrying the Pseudomonas putida F1 toluene dioxygenase (todC1C2BA) genes or the P. pseudoalcaligenes KF707 biphenyl dioxygenase (bphA1A2A3A4) genes was not able to convert these substrates. Surprisingly, E. coli carrying hybrid dioxygenase (todC1::bphA2A3A4) genes with a subunit substitution between the toluene and biphenyl dioxygenases was able to convert fluorene, dibenzofuran, and dibenzothiophene. The cells of a Streptomyces lividans transformant carrying the phenanthrene dioxygenase genes were also evaluated for bioconversion of various tricyclic fused aromatic compounds. The ability of this actinomycete in their conversion was similar to that of E. coli carrying the corresponding genes. Products converted from the aromatic compounds with these recombinant bacterial cells were purified by column chromatography on silica gel, and identified by their MS and 1H and 13C NMR analyses. Several products, e.g., 4-hydroxyfluorene converted from fluorene, and cis-1,2-dihydroxy-1,2-dihydrophenanthridine, cis-9,10-dihydroxy-9,10-dihydrophenanthridine, and 10-hydroxyphenanthridine, which were converted from phenanthridine, were novel compounds.
Multiple site dioxygenase-catalysed cis-dihydroxylation of polycyclic azaarenes to yield a new class of bis-cis-diol metabolites
Boyd, Derek R.,Sharma, Narain D.,Carroll, Jonathan G.,Allen, Christopher C. R.,Clarke, David A.,Gibson, David T.
, p. 1201 - 1202 (2007/10/03)
The enhanced stability of new mono-cis-dihydrodiol bacterial metabolites of tricyclic azaarenes has facilitated the dioxygenase-catalysed formation and isolation of the corresponding bis-cis-dihydrodiols (cis-tetraols) and a three step chemoenzymatic route to the derived arene oxide mammalian metabolites.
Chemical Synthesis of the (1R,2S) and (1S,2R) Arene Oxide Metabolites of Acridine
Boyd, Derek R.,Dorrity, Michael R. J.,Hamilton, Lynne,Malone, John F.,Smith, Allison
, p. 2711 - 2714 (2007/10/02)
Enantiopure samples of (+)-(1R,2S) and (-)-(1S,2R)-1,2-epoxy-1,2-dihydroacridine 4 have been obtained from the corresponding trans-2-bromo-1,2,3,4-tetrahydroacridin-1-ol MTPA esters 7a and b.Absolute configurations were deduced by stereochemical correlation to (+)-(1R,2R)-trans-2-bromo-1-(2-methoxy-2-phenyl-2-trifluoroacetoxy)-1,2,3,4-acridine 7a which was unequivocally assigned by X-ray crystal structure analysis. (-)-(1R,2R)-trans-1,2-Dihydroacridine-1,2-diol 2 was obtained by alkaline hydrolysis of (+)-(1R,2S)-acridine 1,2-oxide 4.
Synthesis and Solvolysis of Acridine 1,2- and 3,4-Oxides: Crystal Structure of Acridine 1,2-Oxide
Boyd, Derek R.,Davies, R. Jeremy H.,Hamilton, Lynne,McCullough, John J.,Malone, John F.,et al.
, p. 984 - 990 (2007/10/02)
Acridine 1,2- and 3,4-oxides were synthesized from 3,4- and 1,2-dihydroacridine, respectively, via intermediate bromohydrin acetates.Crystals of acridine 1,2-oxide were sufficiently stable to allow the first determination of X-ray crystallographic structu
