scholarly journals Oxidation Reactions of Marchantin A Trimethyl Ether and Some Aromatic Compounds using m-Chloroperbenzoic Acid. Formation of Muconic Acid Ester and m-Chlorobenzoate

1999 ◽  
Vol 23 (8) ◽  
pp. 470-471
Author(s):  
Motoo Tori ◽  
Masakazu Sono ◽  
Keiko Takikawa ◽  
Reiko Matsuda ◽  
Masao Toyota ◽  
...  
Keyword(s):  
Aromatic Ring ◽  
Methyl Ether ◽  
Aromatic Compounds ◽  
Acid Ester ◽  
Acid Formation ◽  
Oxidation Reactions ◽  
Muconic Acid ◽  
Trimethyl Ether

On treatment with m-chloroperbenzoic acid, dihydroeugenol methyl ether and marchantin A trimethyl ether afford muconic acid ester derivatives by oxidation of the aromatic ring as well as hydroxylated derivatives; the m-chlorobenzoate of the dihydroeugenol derivative is also observed for the former.

Zum stoffwechsel von aromaten, III. Spaltung von oestratrien-derivaten zu dicarbonsäuren vom typus der muconsäure / On the metabolism of aromatic compounds, III . scission of estratrien derivatives to dicarbonic acids of the muconic acid type

1973 ◽  
Vol 28 (11-12) ◽  
pp. 675-684 ◽  
Author(s):  
G Walter ◽  
E Hecker
Keyword(s):  
Aromatic Ring ◽  
Peracetic Acid ◽  
Aromatic Compounds ◽  
Liver Homogenate ◽  
Muconic Acid ◽  
Molecular Asymmetry ◽  
Acid Type ◽  
Boat Form ◽  
Estrone Derivative ◽  
Estradiol 17Β

Abstract By cleavage of the aromatic ring of 6,7-dihydroxy-tetraline (1) with peracetic acid 1,2-bis-carboxymethylene- cyclohexane (3 a) is obtained. The addition of one mole of water to 3 a leads to 1-hydroxy-1-carboxymethyl-2-carboxymethylene-cyclohexane (4), which is readily converted to the lactone 1-hydroxy-2-carboxymethylene-cyclohexane-γ-lactone-aceticacid-(1) (5). By melting of compound 4 or 5 1,2-dihydroxy-cyclohexane-diaceticacid-1 (1,2) -di-γ-lactone (6) is obtained. 1,2-bis-carboxymethylene-cyclohexane (3 a) shows a molecular asymmetry which is of a type similar as found in atropisomeric compounds. On the basis of conformational considerations it is demonstrated that in the dilactone 6 the cyclohexane ring is stabilized in the boat form. Cleavage of the aromatic A-ring of 2-hydroxy-estradiol- (17β) -acetate (7) with peracetic acid occurs in a manner analogous to that of compound 1, giving rise to 2,3-seco-Δ10(1)-estrenediol- (5ξ, 17β)-diacid-(2,3)-lactone-(2 → 5) -17-acetate (8 a). 8 a is converted to the methylester 9 and further to the corresponding estrone derivative 11 a. Estrone-[16-14C] was incubated with the 15 000 × g supernatant from rat liver homogenate in order to investigate the possibility if scission of the aromatic ring A of estrogens is a step in their katabolism. Substance 11 a was used as a carrier in these studies

scholarly journals An aerobic link between lignin degradation and C1 metabolism: growth on methoxylated aromatic compounds by members of the genus Methylobacterium

2019 ◽  
Author(s):  
Jessica A. Lee ◽  
Sergey Stolyar ◽  
Christopher J. Marx
Keyword(s):  
Comparative Genomics ◽  
Aromatic Ring ◽  
Aromatic Compounds ◽  
Lignin Degradation ◽  
Comprehensive Description ◽  
Aromatic Polymer ◽  
C1 Metabolism ◽  
Polycyclic Aromatic ◽  
Methoxylated Aromatic ◽  
Aromatic Catabolism

AbstractMicroorganisms faces many barriers in the degradation of the polycyclic aromatic polymer lignin, one of which is an abundance of methoxy substituents. Demethoxylation of lignin-derived aromatic monomers in aerobic environments releases formaldehyde, a potent cellular toxin that organisms must eliminate in order to further degrade the aromatic ring. Here we provide the first comprehensive description of the ecology and evolution of the catabolism of methoxylated aromatics in the genus Methylobacterium, a plant-associated genus of methylotrophs capable of using formaldehyde for growth. Using comparative genomics, we found that the capacity for aromatic catabolism is ancestral to two clades, but has also been acquired horizontally by other members of the genus. Through laboratory growth assays, we demonstrated that several Methylobacterium strains can grow on p-hydroxybenzoate, protocatechuate, vanillate, and ferulate; furthermore, whereas non-methylotrophs excrete formaldehyde as a byproduct during growth on vanillate, Methylobacterium do not. Finally, we surveyed published metagenome data to find that vanillate-degrading Methylobacterium can be found in many soil and rhizosphere ecosystems but is disproportionately prominent in the phyllosphere, and the most highly represented clade in the environment (the root-nodulating species M. nodulans) is one with few cultured representatives.

Zum stoffwechsel von aromaten, II. über die muconsäurespaltung von einfachen o-diphenolen / on the metabolism of aromatic compounds, ii * the muconic acid scission of simple o-diphenols

1973 ◽  
Vol 28 (11-12) ◽  
pp. 662-674 ◽  
Author(s):  
Günther Schulz ◽  
Erich Hecker
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Ethyl Acetate ◽  
Peracetic Acid ◽  
Aromatic Compounds ◽  
Time Course ◽  
Protocatechuic Acid ◽  
Uv Light ◽  
Steric Effects ◽  
Muconic Acid

Abstract The preparation of substituted cis,cis-muconic acids by oxidative ring scission of simple o-di-phenols with peracetic acid is investigated. Scission of pyrocatechol (1) to cis,cis-muconic acid (2) gives optimal yields, if acetic acid or ethyl acetate is used as solvent and if the solution is 15-20% with respect to sulfuric acid free peracetic acid comprising a one molar excess of oxidant. Under similar conditions, 3-tosylamino-pyrocatechol yields with peracetic acid the hitherto unknown α-tosylamino-cis,cis-muconic caid (18). 18 may be converted to α-tosylamino-traras,trans-muconic acid (19) by means of iodine, UV light or heating. From protocatechuic acid (4) under similar conditions not β-carboxy-cis,cis-muconic acid (5) is obtained, but rather β-carboxy-mucono-lactone (6 b, γ-carboxymethyl-β-carboxy-Δα-butenolide). As yet, this lactone has been accessible only from an isomer of β-carboxy-cis,cis-muconic acid, the latter being obtainable by enzymatic scission of protocatechuic acid (4). Steric effects are responsible for both, the formation of the free cis,cis-muconic acids 2 and 18 from pyrocatechol (1) and α-tosylamino-pyrocatechol, and the formation of the γ-lactone 6 b instead of β -carboxy-cis,cis-muconic acid by scission of protocatechuic acid (4). The time course of the reactions shows that - compared to pyrocatechol (1) - a 3-tosylamino-group enhances the peracetic acid scission, whereas a 4-carboxygroup as in 4 slows it down

scholarly journals Bioprocess development for muconic acid production from aromatic compounds and lignin

2018 ◽  
Vol 20 (21) ◽  
pp. 5007-5019 ◽  
Author(s):  
Davinia Salvachúa ◽  
Christopher W. Johnson ◽  
Christine A. Singer ◽  
Holly Rohrer ◽  
Darren J. Peterson ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Acid Production ◽  
Process Development ◽  
Bioprocess Development ◽  
Muconic Acid ◽  
Bioreactor Process

This work shows parallel strain and bioreactor process development to improve muconic acid production from aromatic compounds and lignin.

scholarly journals Recent Advances in Microbial Production of cis,cis-Muconic Acid

Biomolecules ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1238 ◽  
Author(s):  
Sisun Choi ◽  
Han-Na Lee ◽  
Eunhwi Park ◽  
Sang-Jong Lee ◽  
Eung-Soo Kim
Keyword(s):  
Metabolic Pathway ◽  
Aromatic Compounds ◽  
Terephthalic Acid ◽  
De Novo ◽  
Vital Role ◽  
Chemical Processes ◽  
Muconic Acid ◽  
Production Strategies ◽  
Culture Process ◽  
Foreign Genes

cis,cis-Muconic acid (MA) is a valuable C6 dicarboxylic acid platform chemical that is used as a starting material for the production of various valuable polymers and drugs, including adipic acid and terephthalic acid. As an alternative to traditional chemical processes, bio-based MA production has progressed to the establishment of de novo MA pathways in several microorganisms, such as Escherichia coli, Corynebacterium glutamicum, Pseudomonas putida, and Saccharomyces cerevisiae. Redesign of the metabolic pathway, intermediate flux control, and culture process optimization were all pursued to maximize the microbial MA production yield. Recently, MA production from biomass, such as the aromatic polymer lignin, has also attracted attention from researchers focusing on microbes that are tolerant to aromatic compounds. This paper summarizes recent microbial MA production strategies that involve engineering the metabolic pathway genes as well as the heterologous expression of some foreign genes involved in MA biosynthesis. Microbial MA production will continue to play a vital role in the field of bio-refineries and a feasible way to complement various petrochemical-based chemical processes.

scholarly journals Epoxy Coenzyme A Thioester Pathways for Degradation of Aromatic Compounds

2012 ◽  
Vol 78 (15) ◽  
pp. 5043-5051 ◽  
Author(s):  
Wael Ismail ◽  
Johannes Gescher
Keyword(s):  
Aromatic Ring ◽  
Aromatic Compounds ◽  
Coenzyme A ◽  
Environmental Pollutants ◽  
Bacterial Degradation ◽  
Ring Cleavage ◽  
The Novel ◽  
Energy Consuming ◽  
Coa Thioesters ◽  
Hydrolytic Mechanism

ABSTRACTAromatic compounds (biogenic and anthropogenic) are abundant in the biosphere. Some of them are well-known environmental pollutants. Although the aromatic nucleus is relatively recalcitrant, microorganisms have developed various catabolic routes that enable complete biodegradation of aromatic compounds. The adopted degradation pathways depend on the availability of oxygen. Under oxic conditions, microorganisms utilize oxygen as a cosubstrate to activate and cleave the aromatic ring. In contrast, under anoxic conditions, the aromatic compounds are transformed to coenzyme A (CoA) thioesters followed by energy-consuming reduction of the ring. Eventually, the dearomatized ring is opened via a hydrolytic mechanism. Recently, novel catabolic pathways for the aerobic degradation of aromatic compounds were elucidated that differ significantly from the established catabolic routes. The new pathways were investigated in detail for the aerobic bacterial degradation of benzoate and phenylacetate. In both cases, the pathway is initiated by transforming the substrate to a CoA thioester and all the intermediates are bound by CoA. The subsequent reactions involve epoxidation of the aromatic ring followed by hydrolytic ring cleavage. Here we discuss the novel pathways, with a particular focus on their unique features and occurrence as well as ecological significance.

Role of tertiary amines in enhancing trihalomethane and haloacetic acid formation during chlorination of aromatic compounds and a natural organic matter extract

2018 ◽  
Vol 4 (5) ◽  
pp. 663-679 ◽  
Author(s):  
Kun Huang ◽  
Amisha D. Shah
Keyword(s):  
Organic Matter ◽  
Organic Compound ◽  
Natural Organic Matter ◽  
Aromatic Compounds ◽  
Acid Formation ◽  
Tertiary Amines ◽  
Haloacetic Acid ◽  
Anthropogenic Inputs

Tertiary amines are prevalent in waters due to anthropogenic inputs and are known to enhance organic compound degradation while increasing disinfection by-product (DBP) formation, via the strong chlorinating agent, R3N–Cl+.

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