砷-生物素缀合物的改进合成方法。
An improved synthesis of arsenic-biotin conjugates.
作者信息
Heredia-Moya Jorge, Kirk Kenneth L
机构信息
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, MD 20892, USA.
出版信息
Bioorg Med Chem. 2008 May 15;16(10):5743-6. doi: 10.1016/j.bmc.2008.03.054. Epub 2008 Mar 27.
Abstract
An amide linked conjugate of p-aminophenylarsine oxide and biotin is conveniently prepared in a one-pot procedure by the reaction of biotinyl chloride, formed in situ, with p-aminophenyldichloroarsine. The reaction of the arsine oxide-biotin conjugate with 1,2-ethanedithiol produces the stabilized dithiarsolane. These reagents are now readily available for a variety of applications.
摘要
对氨基苯胂氧化物与生物素的酰胺连接共轭物可通过原位生成的生物素氯与对氨基苯二氯胂的反应，以一锅法方便地制备。胂氧化物 - 生物素共轭物与1,2 - 乙二硫醇的反应产生稳定的二硫砷环戊烷。这些试剂现在很容易用于各种应用。
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3
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4
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