A Novel Family of Aromatic Diazirines for Photoaffinity Labeling
A Novel Family of Aromatic Diazirines for Photoaffinity Labeling
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用于光亲和标记的新型芳香族二氮丙啶家族
DOI：
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发表时间：
1994
期刊：
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通讯作者：
Y. Kanaoka
中科院分区：
文献类型：
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作者：
Y. Hatanaka;M. Hashimoto;H. Kurihara;H. Nakayama;Y. Kanaoka
完成了一系列简单的芳环双氮杂环丙烷的改性方法。这种涉及在二氮杂环丙烯的芳环上直接取代的第一种通用方法已经通过（烷氧基苯基）二氮杂环丙烯的芳族取代来实现。铊部分的引入成功地通过硝化、碘化或钯催化的羰基化得到一族可用于光标记的取代的芳基二氮杂环丙烷。例如，用硝基标记的二氮杂环丙烷可以通过分光光度法检测，用碘基标记的那些可以用于示踪实验。在一定的脱甲基条件下，（甲氧基苯基）二氮杂环丙烷也是稳定的，从而提供了具有可修饰酚羟基的二氮杂环丙烷的潜在来源。通过这种方法，可以很容易地引入连接二氮杂环丙烷与配体的间隔臂。用此方法还制备了碳-14或氚标记的放射性二氮杂环丙烷。所有新的二氮杂环丙烯均衍生自一对简单的（甲氧基苯基）二氮杂环丙烯。本文所述的（烷氧基苯基）二氮杂环丙烯衍生化的容易性可能提供一种实用的方法来简化目前用于二氮杂环丙烯合成的耗时方法
A series of simple methods for modifying diazirines bearing an aromatic ring has been accomplished. This first versatile approach involving direct substitution on the aromatic ring of diazirines has been achie- ved by means of the aromatic thallation of (alkoxyphenyl)diazirines. Introduction of the thallium moiety was successfully followed by nitra- tion, iodination, or palladium-catalyzed carbonylation to give a family of substituted aryldiazirines useful for photolabeling. For instance, diazirines labeled with a nitro group can be detected by spectrophoto- metric methods, and those labeled with an iodo group can be useful in tracer experiments. The (methoxyphenyl)diazirines were also found to be stable under certain demethylation conditions, thus providing a poten- tial source of diazirines with modifiable phenol hydroxyl groups. By means of this approach, a spacer arm to link diazirines with ligands was readily introduced. Radioactive diazirines labeled with carbon-14 or tritium were also prepared using this method. All the new diazirines were derived from a pair of simple (methoxyphenyl)diazirines. The ease of derivatization of the (alkoxyphenyl)diazirines described here may offer a practical approach to simplify the time-consuming methods currently used for diazirine synthesis