Cobalt-Catalyzed C–H Acetoxylation of Phenols with Removable Monodentate Directing Groups: Access to Pyrocatechol Derivatives. Other routes to catechol include alkaline hydrolysis of o-chlorophenol and Fries peroxide rearrangement of salicylaldehyde, but these are no longer commercially viable. Biocatalytic Conversion of D-glucose to Catechol Using Plasmid p2-47. to access the full features of the site or access our. The strain E. coli AB2834/pKD136 was then transformed with plasmid p2-47. At this limiting level of aromatic amino acid biosynthesis, amplification of the catalytic levels of the pentose phosphate pathway enzyme transketolase achieves sizable increases in the percentage of D-glucose siphoned into the pathway. You have to login with your ACS ID befor you can login with your Mendeley account. Fetching data from CrossRef. 8~ The synthesis of arylalanine suffers from racemization induced by the base, but the optically pure compound is finally obtained when using anhydrous K2CO 3 suspended in toluene (Eq. Such mutants are unable to catalyze the conversion of 3-dehydroshikimate (DHS) into chorismate due to a mutation in one or more of the genes encoding shikimate dehydrogenase, shikimate kinase, EPSP synthase or chorismate synthase, and will thus accumulate elevated intracellular levels of DHS. If you are not the author of this article and you wish to reproduce material from I. Enzymatic formation of catechol from benzene. Catechuic acid and ethyl 2,4,5-trihydroxybenzoate from d-glucose. Corresponding authors, a This surge of carbon flow is then delivered intact into DHS synthesis by pKD136 due to amplified expression of DHQ synthase (encoded by aroB). The metabolic route for the degradation of benzene in Pseudomonas is through the production of cis-benzene glycol after oxidation of the benzene ring, to catechol and finally to cis, cis muconate or 2-hydroxysemialdehyde. In addition, catechol concentrations higher than 10 mg l−1 significantly decreased both benzene and catechol associated respiration, confirming the highly inhibitory effect of this intermediate. Microbial Degradation of Organic Compounds. Biomass-derived carbon sources useable in accordance with this invention include any carbon sources capable of being biocatalytically converted into D-erythrose 4-phosphate (E4P) and phosphoenolpyruvate (PEP), two precursor compounds to the common pathway of aromatic amino acid biosynthesis (see FIG. In situ resin-based extraction of protocatechaute synthesized by E. coli KL3/pWL2.46B followed by chemical decarboxylation of this catechol percursor was then examined. Haoran Zhang, Brian Pereira, Zhengjun Li, Gregory Stephanopoulos. The present invention provides methods for the microbial biosynthesis of catechol from readily available carbon sources capable of biocatalytic conversion to D-erythrose 4-phosphate (E4P) and phosphoenolpyruvate (PEP) in microorganisms having a common pathway of aromatic amino acid biosynthesis. The cells were harvested a second time and then resuspended in 2 mL of Buffer A per gram of cellular wet weight. This invention relates to the production of catechol and precursors thereof by the conversion of biomass-derived carbon sources. Amplified expression of DHQ synthase removes the rate-limiting character of this enzyme, and prevents the accumulation of DAHP and its nonphosphorylated analog, DAH. Regulation of Expression of Genes Involved in Quinate and Shikimate Utilization in Corynebacterium glutamicum. Preferred host organisms are mutant strains of Escherichia coli genetically engineered to express selected genes endogenous to Klebsiella pneumoniae. Benzene-Free Synthesis of Catechol: Interfacing Microbial and Chemical Catalysis, Contribution from the Department of Chemistry, Michigan State University, East Lansing, Michigan 48824. Facile biocatalytic synthesis of a macrocyclic lactone in sub- and supercritical solvents. Except for acetate (δ1.9, s, 3H), no other products of significant concentration were detected in the culture supernatant. & Terms of Use. As further verification that the 3.5 kb BamH I fragment encoded the aroZ gene, cell extracts were assayed for DHS dehydratase activity. Janke D and Ihn W 1989 Cometabolic turnover of aniline, phenol and some of their monochlorinated derivatives by the. Additional objects, features, and advantages of the invention will become apparent to those skilled in the art upon consideration of the following detailed description of preferred embodiments exemplifying the best mode of carrying out the invention as presently perceived. A preferred means for introducing genetic elements into a host cell utilizes an extrachromosomal multi-copy plasmid vector into which genetic elements in accordance with the present invention are inserted. 50, 2875–2880. Find more information on the Altmetric Attention Score and how the score is calculated. Acetic acid will be another product of the reaction. The result is a divergent pathway in which carbon flow originally directed into the common pathway of aromatic amino acid biosynthesis is directed to protocatechuate from DHS, and thereafter to produce catechol from protocatechuate. The genetic elements of the present invention can be introduced into a host cell by plasmids, cosmids, phages, yeast artificial chromosomes or other vectors that mediate transfer of the genetic elements into a host cell. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. Inhibitory effects of catechol accumulation on benzene biodegradation in. Biosynthesis of catechol melanin from glycerol employing metabolically engineered Escherichia coli. Cemiglia C E 1992 Biodegradation of polycyclic aromatic hydrocarbons. Hopper D J 1978 Microbial degradation of hydrocarbons. Plasmid borne introduction of the genetic element into host cells involves an initial cleaving of a plasmid with a restriction enzyme, followed by ligation of the plasmid and genetic elements in accordance with the invention. After incubation at 37° C. for approximately 24 h, colony 2-47 was producing a local region of brown that was lacking from all other colonies. More particularly this invention is directed to the biocatalytic conversion of glucose, and other sugars capable of being used in the biosynthesis of aromatic amino acids, to catechol by way of 3-dehydroshikimate and protocatechuate. Biochem. Although some such microbes have been identified, the substrates for their biocatalytic activity are benzene or phenol. 266, 2223–2228. Based on the experimental results and kinetics, possible reaction mechanisms are proposed. E-mail: Therefore, amplified expression of aroF-encoded DAHP synthase, tkt-encoded transketolase and aroB-DHQ synthase increases production of DHS, which in the presence of DHS dehydratase and protocatechuate decarboxylase is converted to catechol. The fact that pSU1-28 results in higher DHS dehydratase activity likely indicates that the aroZ gene is transcribed from the vector encoded lac promoter as well as from its native K. pneumoniae promoter in this plasmid construct. The enzymes in the common pathway, and their respective genes, include DAHP synthase (aroF), DHQ synthase (aroB), DHQ dehydratase (aroD), shikimate dehydrogenase (aroE), shikimate kinase (aroL, aroK), EPSP synthase (aroA) and chorismate synthase (aroC). Tech. The reaction of 2 with [AuCl(SMe2)] also afforded a tetranuclear complex [{((μ-N(tBu)P)2)2(μ-C6H2O4)}{AuCl}4] (16). In R J Watkinson (Ed.). pp 389-400 | The problematic extraction of these catechol precursors from culture medium was subsequently circumvented by high-yielding chemical dehydration of 3-dehydroquinate and 3-dehydroshikimate in culture medium followed by extraction of the resulting protocatechuate. Treatment of 1 with [RuCl2(η6-p-cymene)]2, [Rh(COD)Cl]2 and [Pd(η3-C3H5)Cl]2 in 1 : 1 molar ratios produced dinuclear complexes [{(μ-N(tBu)P)2(C6H4O2)}{RuCl2(η6-p-cymene)}2] (9), [{(μ-N(tBu)P)2(C6H4O2)}{RhCl(COD)}2] (10) and [{(μ-N(tBu)P)2(C6H4O2)}{PdCl(η3-C3H5)}2] (11), respectively.
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