Synthesis of the non-K-region o-quinones and dihydrodiols of polycyclic aromatic hydrocarbons from the corresponding phenols

Sukumaran, Kutikat B.; Harvey, Ronald G.

doi:10.1021/jo01310a029

Cited by 57 publications

(29 citation statements)

References 2 publications

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“…Both reactions were regiospecific within experimental limits. An alternative reagent that has also been employed for oxidation of PAPs is phenylseleninic anhydride [(PhSeO) 2 O], 20 also known as Barton’s reagent. It tends to furnish predominantly the ortho -PAQ isomers, but the results are variable.…”

Section: Discussionmentioning

confidence: 99%

Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

Duan

et al. 2010

Tetrahedron

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The hypervalent iodine reagents o-iodoxybenzoic acid (IBX) and bis(trifluoro-acetoxy)iodobenzene (BTI) are shown to be general reagents for regio-controlled oxidation of polycyclic aromatic phenols (PAPs) to specific isomers (ortho, para, or remote) of polycyclic aromatic quinones (PAQs). The oxidations of a series of PAPs with IBX take place under mild conditions to furnish the corresponding ortho-PAQs. In contrast, oxidations of the same series of PAPs with BTI exhibit variable regiospecificity, affording para-PAQs where structurally feasible and ortho-PAQs or remote PAQ isomers in other cases. The structures of the specific PAQ isomers formed are predictable on the basis of the inherent regioselectivities of the hypervalent iodine reagents in combination with the structural requirements of the phenol precursors. IBX and BTI are recommended as the preferred reagents for regio-controlled oxidation of PAPs to PAQs.

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Section: Discussionmentioning

confidence: 99%

Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

Duan

et al. 2010

Tetrahedron

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“…13. The quinones synthesized include: naphthalene-1,2-dione (NP-1,2-dione) [56], phenanthrene-1,2-dione [57] [58,59].…”

Section: Properties Of Pah O-quinones Produced By Akrsmentioning

confidence: 99%

Aldo-Keto Reductases and Formation of Polycyclic Aromatic Hydrocarbon o-Quinones

Penning¹

2004

Quinones and Quinone Enzymes, Part A

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IntroductionAldo-Keto Reductases (AKRs) are a rapidly growing protein superfamily that is highly conserved across prokaryotes and eukaroytes [1,2]. These are generally monomeric NAD(P) H linked oxidoreductases, that are soluble, and consist of approximately 320 amino acids and have mol. wts = 34-37 kDa. These enzymes often convert carbonyl containing substrates to alcohols; aldehydes are converted to primary alcohols and ketones are converted to secondary alcohols. When the carbonyl functionality is found on a natural substrate (steroid hormone or prostaglandin) or a drug or xenobiotic, conversion to the corresponding alcohol functionalizes the product for conjugation and elimination. These enzymes thus play a central role in the metabolism of endogenous substrates, drugs, xenobiotics, and carcinogens and are likely to be as important as the CYP superfamily in dealing with toxic insults.Currently, there are 114 members in the AKR superfamily distributed across 14 families. For a complete listing and nomenclature visit www.med.upenn.edu/akr. Proteins that belong to separate families have less than 40% sequence identity, and proteins that have greater than 60% similarity belong to the same subfamily. Each of the AKRs have common properties. They catalyze an ordered bi-bi reaction in which pyridine nucleotide binds first and leaves last. They are A-face specific dehydrogenases and catalyze the transfer of the 4-pro-R-hydride ion from the nicotinamide cofactor to the acceptor carbonyl [3]. NADP(H) binding is accompanined by the formation of a loose complex that isomerizes to a tight complex [4,5]. The rate of release of NADP + is a slow event and is controlled by the slow isomerization of the tight-complex to the loose-complex prior to release of cofactor.There are 13 crystal structures of AKRs in the PDB. Each crystal structure has a common (α/ β) 8 -barrel motif, in which an α-helix and a β-strand alternate 8-times [6][7][8]. The β-strands coalesce at the core of the structure to comprise the staves of a barrel, Fig. 1. In the available ternary complexes, the cofactor lies across the lip of the barrel and the substrate is orientated perpendicular to the cofactor. Three large loops at the back of the barrel define substrate specificity. At the base of the barrel a catalytic tetrad exists that is almost entirely conserved across the superfamily and consists of Tyr, Lys, His and Asp; where the catalytic tyrosine functions as the general acid-base in the proton relay to the substrate [9].Several AKRs have been implicated in carcinogen metabolism, these include the dihydrodiol dehydrogenases that oxidize polycyclic aromatic hydrocarbon trans-dihydrodiols to reactive and redox-active o-quinones (AKR1C1-AKR1C4 and AKR1A1) [10][11][12][13][14]; the NNK (4-(Nmethyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone) carbonyl reductases that reduce tobaccospecific nitrosamino-ketones (NNK) to the corresponding alcohols (AKR1C1-AKR1C4) [ NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript and the aflatoxin dialde...

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“…YEASTMAKER yeast transformation and plasmid isolation kit and all yeast culture media were obtained from CLON-TECH (Palo Alto, California, USA). BP-7,8-dione were synthesized according to the published routes (19). N -methyl-N -nitro-N -nitrosoguanidine (MNNG) and (±)-anti-BPDE were obtained from the National Cancer Institute, Chemical Carcinogen Standard Reference Repository (Kansas City, Missouri, USA).…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

POLYCYCLIC AROMATIC HYDROCARBONO-QUINONES MUTATEp53 IN HUMAN LUNG ADENOCARCINOMA (A549) CELLS

Penning¹,

Shen²,

Mick³

et al. 2004

Polycyclic Aromatic Compounds

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Synthesis of the non-K-region o-quinones and dihydrodiols of polycyclic aromatic hydrocarbons from the corresponding phenols

Cited by 57 publications

References 2 publications

Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

Aldo-Keto Reductases and Formation of Polycyclic Aromatic Hydrocarbon o-Quinones

POLYCYCLIC AROMATIC HYDROCARBONO-QUINONES MUTATEp53 IN HUMAN LUNG ADENOCARCINOMA (A549) CELLS

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