Reaktionen mit Nitrosodisulfonat, V. Mitteil.): Über die Bildung von Naphtochinonen

Teuber, Hans‐Joachim; Götz, Norbert

doi:10.1002/cber.19540870908

Cited by 77 publications

(22 citation statements)

References 9 publications

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“…The genetic information for the degradation of naphthalene by bacteria is often carried by plasmids (2,6,7,10,14,15,39 (5,11). Nevertheless, some distinct differences between the two pathways exist.…”

Section: Resultsmentioning

confidence: 99%

Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids

et al. 1991

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1,2-Dihydroxynaphthalene dioxygenase was purified to homogeneity from a bacterium that degrades naphthalenesulfonic acids (strain BN6). The enzyme requires Fe2" for maximal activity and consists of eight identical subunits with a molecular weight of about 33,000. Analysis of the NH2-terminal amino acid sequence revealed a high degree of homology (22 of 29 amino acids) with the NH2-terminal amino acid sequence of 2,3-dihydroxybiphenyl dioxygenase from strain Pseudomonas paucimobiis Ql. 1,2-Dihydroxynaphthalene dioxygenase from strain BN6 shows a wide substrate specificity and also cleaves 5-, 6-, and 7-hydroxy-1,2-dihydroxynaphthalene, 2,3-and 3,4-dihydroxybiphenyl, catechol, and 3-methyl-and 4-methylcatechol. Similar activities against the hydroxy-1,2-dihydroxynaphthalenes were also found in cell extracts from naphthalenedegrading bacteria.Amino-and hydroxynaphthalenesulfonic acids (ANS and HNS, respectively) serve as building blocks for the largescale synthesis of azo dyes. Since arylsulfonates are very rare among natural compounds (21), naphthalenesulfonic acids are referred to as xenobiotics. Arylsulfonates are major pollutants of the environment, and the contamination of the Rhine River by sulfur-organic compounds is largely due to this class of compounds (25). Nevertheless, bacteria which degrade naphthalenesulfonic acids have repeatedly been isolated (4, 5, 29-31, 41, 43). Brilon et al. (4, 5) selected pseudomonads which degraded naphthalene-2-sulfonic acid (2NS) and naphthalene-1-sulfonic acid (1NS). The initial reaction in the degradation of iNS and 2NS is catalyzed by a 1,2-dioxygenase which weakens the carbon-sulfur bond.

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Section: Resultsmentioning

confidence: 99%

Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids

et al. 1991

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“…Compound 1 was prepared from naphthalen‐1,2‐diol ( 5 ) under different conditions as following potassium oxide (KO 2 ) in pyridine or toluene at −10°C for 6 h ; crown‐ether in pyridine or toluene for 5 min ; KO 2 and tetraethyl ammonium bromide (Et 4 NBr) in DMF at 20°C ; or oxygen and aqueous–methanolic alkaline solution . Treatment of naphthalen‐1,3‐diol ( 6 ) with zirconium phosphate, phthalocyanine[Fe 3+ ], and oxygen in acetone at 20°C for 6 h in yield 80% ; or crown‐ether in pyridine or toluene for 5 min in yield 60% ; or KOH and air ; or Fremy's salt (K 4 [ON(SO 3 ) 2 ] 2 ) in methanol ; or air ; or KO 2 in THF or toluene at −10°C for 6 h afforded 1 . The chemical reaction of 1,4‐dihydroxynaphthequinone 7 with KO 2 in tetrahydrofuran (THF) and toluene for 6 h at −10°C , or with NaOH, H 3 It, VO 2 (O 2 ) 2 , and H 2 O 2 afforded compound 1 .…”

Section: Synthesis Of 2‐hydroxynaphthalen‐14‐dionementioning

confidence: 99%

Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione)

Hamama

Hassanien

Zoorob

2017

Journal of Heterocyclic Chem

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“…However, this method is too drastic and results in low yields (56). Somewhat better yields are obtained by using Fremy's salt (potassium nitroso disulfonate) as the oxidant (57). By using thallium trinitrate to oxidize 1,5-dihydroxynaphthalene, yields as high as 70% of juglone have been reported (58).…”

Section: Naphthoquinone Dyesmentioning

confidence: 99%

Dyes, Natural

Cofrancesco¹

2009

Kirk-Othmer Encyclopedia of Chemical Technology

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From the earliest times humans admired the beautiful natural colors of plants and minerals and sought to enhance human appearance by color. Ancient peoples used these dyes in cosmetics,food, and as medicine. The greatest use of natural dyes occurred when the art of weaving was developed. A few synthetic dyes were manufactured before 1856, but the big break through in synthetic dye manufacture came from Perkin who developed the synthesis for the dye Mauve. Synthetic dyes replaced natural dyes, but natural dyes are making a comeback. Hand dyeing is popular and there is an ever increasing demand for natural dyes as food colorings. This article discusses those natural dyes formerly manufactured. Basic categores include anthraquinones; napthoquinone dyes; indigoid dyes, and the natural food colors.The use of biogenic sources for color is a common practice, and for the most part, these do not produce adverse reactions. However, a few biogenic substances have been linked to allergic type reactions. Literature makes reference to carmine and annatto. Regulations of natural dyes are not numerous, but are discussed here.

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Reaktionen mit Nitrosodisulfonat, V. Mitteil.): Über die Bildung von Naphtochinonen

Cited by 77 publications

References 9 publications

Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids

Purification and characterization of a 1,2-dihydroxynaphthalene dioxygenase from a bacterium that degrades naphthalenesulfonic acids

Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione)

Dyes, Natural

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