Enzymatic aziridine synthesis from β amino-alcohols—a new example of endogenous carcinogen formation

Bicker, U.; Fischer, W.

doi:10.1038/249344a0

Cited by 32 publications

(7 citation statements)

References 3 publications

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“…256 In this work, compound 201 was incubated with homogenized rat liver extract (Scheme 35). In the presence of both ATP and sulfate, 201 was converted to an aziridine compound ( 203 ).…”

Section: Aziridine Biosynthesismentioning

confidence: 99%

Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis

2011

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“…256 In this work, compound 201 was incubated with homogenized rat liver extract (Scheme 35). In the presence of both ATP and sulfate, 201 was converted to an aziridine compound ( 203 ).…”

Section: Aziridine Biosynthesismentioning

confidence: 99%

Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis

2011

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“…Sulfation could facilitate aziridine ring formation resulting in 29 . Precedence for the sulfotransferase mediated step comes from experiments with a rat liver homogenate in which conversion of ephedrine to aziridine is observed in the presence of ATP and sulfate . Subsequent formation of aziridine 31 could either occur spontaneously or be enzyme-catalyzed.…”

mentioning

confidence: 99%

Priming of Azabicycle Biosynthesis in the Azinomycin Class of Antitumor Agents

et al. 2017

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The biosynthesis of the azabicyclic ring system of the azinomycin family of antitumor agents represents the "crown jewel" of the pathway and is a complex process involving at least 14 enzymatic steps. This study reports on the first biosynthetic step, the inroads, in the construction of the novel aziridino [1,2-a]pyrrolidine, azabicyclic core, allowing us to support a new mechanism for azabicycle formation.

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“…Arene oxides also react with other cellular nitrogen nucleophiles to give -amino alcohols, which can be metabolized by sulfotransferase enzymes in arene imines (aziridines) [82][83][84][85], the nitrogen analogues of arene oxides. Arene imines have been shown to be considerably more mutagenic than the corresponding epoxides [86][87][88][89][90][91].…”

Section: Carbocations From Miscellaneous Het-ero-pahsmentioning

confidence: 99%

Quantum Chemical Studies on Ultimate Carcinogenic Metabolites from Polycyclic Aromatic Hydrocarbons

Borosky

2008

CMC

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Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental pollutants well known as mutagenic/carcinogenic agents. This review will discuss recent theoretical studies regarding the stability and reactivity of ultimate carcinogenic metabolites from PAHs, focusing on their diol epoxide and amine derivatives. Geometrical and electronic features will be analyzed in order to obtain structure-activity relationships. Charge delocalization modes (positive charge density distribution), substituent effects, and conformational aspects will be considered. Computed properties will be compared with the available biological activity data. Correlations between experimental mutagenic potencies reported in the literature and calculated reaction energies and electronic properties will be shown. Heteroaromatic compounds (aza-PAHs, thia-PAHs, and heteroaromatic amines) will also be examined. To model the important step of covalent adduct formation, calculation of the adducts resulting from bond formation between some of these electrophilic intermediates and nucleotide bases (guanine, cytosine) will be described.

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Enzymatic aziridine synthesis from β amino-alcohols—a new example of endogenous carcinogen formation

Cited by 32 publications

References 3 publications

Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis

Enzymatic Chemistry of Cyclopropane, Epoxide, and Aziridine Biosynthesis

Priming of Azabicycle Biosynthesis in the Azinomycin Class of Antitumor Agents

Quantum Chemical Studies on Ultimate Carcinogenic Metabolites from Polycyclic Aromatic Hydrocarbons

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