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    Synthesis of carbon-14, carbon-13 and deuterium labeled forms of thioacetamide and thioacetamide S-oxide

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    Sarma_2011.pdf (678.8Kb)
    Issue Date
    2011-11
    Author
    Sarma, Diganta
    Hanzlik, Robert P.
    Publisher
    Wiley
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
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    Abstract
    Thioacetamide (TA) is a model hepatotoxin that undergoes metabolic activation via two successive S-oxidations. The ultimate toxic metabolite thioacetamide S,S-dioxide, or its tautomer acetimidoyl sulfinic acid CH3C(NH)SO2H, then acylates lysine side chains on cellular proteins leading to cellular dysfunction or death. To identify individual target proteins, quantitate the extent of their modification and elucidate the structural details of their modification we required both radio-labeled and stable-labeled forms of TA and its intermediate metabolite thioacetamide S-oxide (TASO). The latter is stable when purified but can be difficult to isolate. Considering currently available isotopic precursors we devised and report here methods for the synthesis and isolation of TA and TASO labeled with C-14, C-13 and/or deuterium. The methods are straightforward, utilize readily available precursors and are amenable to small scale.
    Description
    This is the peer reviewed version of the following article: Sarma, D., & Hanzlik, R. P. (2011). Synthesis of carbon-14, carbon-13 and deuterium labeled forms of thioacetamide and thioacetamide S-oxide. Journal of Labelled Compounds & Radiopharmaceuticals, 54(13), 795–798. http://doi.org/10.1002/jlcr.1933, which has been published in final form at http://doi.org/10.1002/jlcr.1933. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
    URI
    http://hdl.handle.net/1808/24288
    DOI
    https://doi.org/10.1002/jlcr.1933.
    Collections
    • Medicinal Chemistry Scholarly Works [242]
    Citation
    Sarma, D., & Hanzlik, R. P. (2011). Synthesis of carbon-14, carbon-13 and deuterium labeled forms of thioacetamide and thioacetamide S-oxide. Journal of Labelled Compounds & Radiopharmaceuticals, 54(13), 795–798. http://doi.org/10.1002/jlcr.1933

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    785-864-8983
    KU Libraries
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    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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