The Dienone—Phenol Rearrangement

Arnold, Richard T.; Buckley, Jay S.; Richter, John W.

doi:10.1021/ja01202a022

Cited by 51 publications

(21 citation statements)

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“…An interesting novelty is that HcdA hydroxylase produces only one product, which has the ipso -group shifted to the meta -position. Therefore, we propose that in the case of HcdA, NIH shift occurs enzymatically, but not spontaneously or by a dienone-phenol rearrangement mechanism [ 62 ], since all bioconversions were performed under neutral or basic conditions. Although a further investigation is needed to determine the exact mechanism of the HcdA enzyme activity.…”

Section: Discussionmentioning

confidence: 99%

Biodegradation of 7-Hydroxycoumarin in Pseudomonas mandelii 7HK4 via ipso-Hydroxylation of 3-(2,4-Dihydroxyphenyl)-propionic Acid

Krikštaponis

Meškys

2018

Molecules

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A gene cluster, denoted as hcdABC, required for the degradation of 3-(2,4-dihydroxyphenyl)-propionic acid has been cloned from 7-hydroxycoumarin-degrading Pseudomonas mandelii 7HK4 (DSM 107615), and sequenced. Bioinformatic analysis shows that the operon hcdABC encodes a flavin-binding hydroxylase (HcdA), an extradiol dioxygenase (HcdB), and a putative hydroxymuconic semialdehyde hydrolase (HcdC). The analysis of the recombinant HcdA activity in vitro confirms that this enzyme belongs to the group of ipso-hydroxylases. The activity of the proteins HcdB and HcdC has been analyzed by using recombinant Escherichia coli cells. Identification of intermediate metabolites allowed us to confirm the predicted enzyme functions and to reconstruct the catabolic pathway of 3-(2,4-dihydroxyphenyl)-propionic acid. HcdA catalyzes the conversion of 3-(2,4-dihydroxyphenyl)-propionic acid to 3-(2,3,5-trihydroxyphenyl)-propionic acid through an ipso-hydroxylation followed by an internal (1,2-C,C)-shift of the alkyl moiety. Then, in the presence of HcdB, a subsequent oxidative meta-cleavage of the aromatic ring occurs, resulting in the corresponding linear product (2E,4E)-2,4-dihydroxy-6-oxonona-2,4-dienedioic acid. Here, we describe a Pseudomonas mandelii strain 7HK4 capable of degrading 7-hydroxycoumarin via 3-(2,4-dihydroxyphenyl)-propionic acid pathway.

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Section: Discussionmentioning

confidence: 99%

Biodegradation of 7-Hydroxycoumarin in Pseudomonas mandelii 7HK4 via ipso-Hydroxylation of 3-(2,4-Dihydroxyphenyl)-propionic Acid

Krikštaponis

Meškys

2018

Molecules

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“…Tetralone XVII was prepared by the method of Arnold et al (13). Tetralone XVIII, first reported by Mukherjee (14), was prepared in 53% yield by a one-step process involving treatment of a mixture of y,y-dimethylbutyrolactone and anisole with polyphosphoric acid.…”

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confidence: 99%

Substituted tetralins I: Synthesis and Analgesic Activities of Some 2-Aminotetralins

Martin

Parulkar

Gusseck

et al. 1969

Journal of Pharmaceutical Sciences

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“…(2008). E64, o509-o510 (Arnold et al, 1947). Its conformational analysis has also been reported (Kerbal et al, 1990).…”

Section: S2 Experimentalmentioning

confidence: 77%

“…For the crystal structure of a very similar compound, 3-(4chlorophenyl)-4-(4-phenyl-3 0 ,4 0 -dihydro-1 0 H,4H-spiro[isoxazole-5,2 0 -naphthalen]-1 0 -one, see: Subbiah Pandi et al (2001). For related literature, see: Anaflous et al (2004); Arnold et al (1947); Bakavoli et al (2005); Chaouni-Benabdallah et al (2001); Chenera et al (1993); Debaerdemaeker et al (1977); Ellis (1997); Howe & Shelton (1990); Katritzky et al (2003); Kerbal et al (1990); Kooijman et al (1984); Seifert et al (1976); Smietana et al (1999).…”

Section: Related Literaturementioning

confidence: 99%

4′-Methyl-3-(4-nitrophenyl)-4-phenyl-4,5,1′,2′,3′,4′-hexahydrospiro[isoxazole-5,2′-naphthalen]-1′-one

Alhouari

Kerbal

Larbi³

et al. 2008

Acta Cryst E

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The title compound, C25H20N2O4, is a new spiro-isoxazoline derivative. It contains a five-membered isoxazoline ring (A), a tetralone unit (E and D), a 4-nitrophenyl substituent (B), and a phenyl ring (C). The isoxazoline ring (A) has an envelope conformation, while the cyclohexenone ring (D) has an intermediate sofa/half-chair conformation. The aromatic ring of the 4-nitrophenyl substituent (B) is inclined at an angle of 78.97 (10)° to the phenyl ring (C). The rigid pharmacophore site, Osp 2—C—C—Osp 3, is characterized by an O⋯O distance of 3.113 (2) Å and an O—C—C—O torsion angle of 97.8 (2)°. In the crystal structure, molecules are linked by C—H⋯O contacts.

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The Dienone—Phenol Rearrangement

Cited by 51 publications

References 0 publications

Biodegradation of 7-Hydroxycoumarin in Pseudomonas mandelii 7HK4 via ipso-Hydroxylation of 3-(2,4-Dihydroxyphenyl)-propionic Acid

Biodegradation of 7-Hydroxycoumarin in Pseudomonas mandelii 7HK4 via ipso-Hydroxylation of 3-(2,4-Dihydroxyphenyl)-propionic Acid

Substituted tetralins I: Synthesis and Analgesic Activities of Some 2-Aminotetralins

4′-Methyl-3-(4-nitrophenyl)-4-phenyl-4,5,1′,2′,3′,4′-hexahydrospiro[isoxazole-5,2′-naphthalen]-1′-one

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