Reactome | Vinyl chloride is oxidized to 2-Chloroethylene oxide

Vinyl chloride is oxidized to 2-Chloroethylene oxide

Stable Identifier

R-HSA-76354

Type

Reaction [transition]

Species

Homo sapiens

Compartment

smooth endoplasmic reticulum

ReviewStatus

5/5

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Metabolism (Homo sapiens)

- Biological oxidations (Homo sapiens)
  - Phase I - Functionalization of compounds (Homo sapiens)
    - Cytochrome P450 - arranged by substrate type (Homo sapiens)
      - Xenobiotics (Homo sapiens)
        
        CYP2E1 reactions (Homo sapiens)
        
        Vinyl chloride is oxidized to 2-Chloroethylene oxide (Homo sapiens)

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Vinyl chloride is oxidized to 2-Chloroethylene oxide

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CYP2E1 can catalyze the oxidation of the vinyl halide vinyl chloride to the epoxide 2-chloroethylene oxide. The epoxide is very unstable and rearranges quickly to 2-chloroacetaldehyde. Both these products can interact with DNA and proteins.

Literature References

PubMed ID	Title	Journal	Year
1664256	Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects Guengerich, FP, Kim, DH, Iwasaki, M	Chem Res Toxicol	1991
497175	Activation of vinyl chloride to covalently bound metabolites: roles of 2-chloroethylene oxide and 2-chloroacetaldehyde Guengerich, FP, Crawford, WM Jr, Watanabe, PG	Biochemistry	1979