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    Alkylating esters. X. The reaction of some aziridine alkylating agents with methionine and S-methyl cysteine.

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    Authors
    Jones, A R
    Capps, P A
    Affiliation
    Paterson Laboratories, Christie Hospital and Holt Radium Institute, Manchester
    Issue Date
    1977-02
    
    Metadata
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    Abstract
    Two biologically active aziridine ring-containing compounds, N,N-ethylene urethane (I) and N,N-ethylene urea (II), have been shown to react with methionine in dilute phosphate buffer (pH 7.4) at 37 degree C. Degradative procedures indicate that the aziridine ring effectively alylates the thio ether group of methionine and other thio ether-containing amino acids to produce sulphonium salts (V). By using [35S]methionine, the sulphonium salts have been shown to be quite stable under physiological conditions (t1/2 7--9 days) hydrolysing to convert the methionine residue to homoserine. It is proposed that similar alkylations of methionyl residues in vivo by aziridine-alkylating agents may explain the complex, and al yet unknwn, metabolic fate of the aziridine ring and could also be a factor contributing to the diverse effects that these agents have on living cells.
    Citation
    Alkylating esters. X. The reaction of some aziridine alkylating agents with methionine and S-methyl cysteine. 1977, 16 (2):181-9 Chem Biol Interact
    Journal
    Chemico-Biological Interactions
    URI
    http://hdl.handle.net/10541/144874
    DOI
    10.1016/0009-2797(77)90127-2
    PubMed ID
    849623
    Type
    Article
    Language
    en
    ISSN
    0009-2797
    ae974a485f413a2113503eed53cd6c53
    10.1016/0009-2797(77)90127-2
    Scopus Count
    Collections
    All Paterson Institute for Cancer Research

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