Synthesis of carbon-14, carbon-13 and deuterium labeled forms of thioacetamide and thioacetamide S-oxide
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Issue Date
2011-11Author
Sarma, Diganta
Hanzlik, Robert P.
Publisher
Wiley
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
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Show full item recordAbstract
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.
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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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