The reaction of protein amino groups with methyl 5-iodopyridine-2-carboximidate. A possible general method of preparing isomorphous heavy-atom derivatives of proteins.
The reaction of protein amino groups with methyl 5-iodopyridine-2-carboximidate. A possible general method of preparing isomorphous heavy-atom derivatives of proteins.
复制标题
蛋白质氨基与 5-碘吡啶-2-甲酰亚胺甲酯的反应。
DOI：
10.1042/bj1310625g
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发表时间：
1973
期刊：
影响因子：
--
通讯作者：
R. Perham
中科院分区：
文献类型：
--
作者：
M. Riley;R. Perham
1.报道了5-碘吡啶-2-甲亚胺酸甲酯的合成及其与模型化合物和过氧甲酸氧化胰岛素的氨基反应。该试剂被设计用于将重原子引入蛋白质的特定位点。2.与氧化胰岛素的氨基的特异性反应可以在合理温和的条件下实现，产生相应的N-单取代脒。3.该试剂与蛋白质氨基的反应程度可以通过差示光谱法容易地确定。赖氨酸残基的修饰抑制了这些残基的胰蛋白酶切割，这有助于在一级结构中建立修饰位点。4.有证据表明，5-碘吡啶-2-甲亚胺酸甲酯可以特异性地在pH 5.0下与3-氨基-1-酪氨酸的芳香氨基反应，该反应的最终产物是2-芳基苯并恶唑。5.使用这种试剂作为一种通用的方法，用于制备蛋白质的重原子同晶衍生物进行了讨论。
1. The synthesis of methyl 5-iodopyridine-2-carboximidate and its reaction with amino groups of model compounds and performic acid-oxidized insulin are described. The reagent was designed to introduce heavy atoms into specific sites in proteins. 2. Specific reaction with the amino groups of oxidized insulin can be achieved under reasonably mild conditions giving rise to the corresponding N-monosubstituted amidines. 3. The extent of reaction of this reagent with protein amino groups can be readily determined by difference spectroscopy. Modification of lysine residues inhibits tryptic cleavage at such residues, and this can be of assistance in establishing the site of modification in the primary structure. 4. Evidence is presented to show that methyl 5-iodopyridine-2-carboximidate can react specifically, at pH5.0, with the aromatic amino group of 3-amino-l-tyrosine; the final product of this reaction is a 2-arylbenzoxazole. 5. The use of this reagent as a general method for preparing heavy-atom isomorphous derivatives of proteins is discussed.