About: NIH shift

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An NIH shift is a chemical rearrangement where a hydrogen atom on an aromatic ring undergoes an intramolecular migration primarily during a hydroxylation reaction. This process is also known as a 1,2-hydride shift. These shifts are often studied and observed by isotopic labeling. An example of an NIH shift is shown below: In this example, a hydrogen atom has been isotopically labeled using deuterium (shown in red). As the hydroxylase adds a hydroxyl (the −OH group), the labeled site shifts one position around the aromatic ring relative to the stationary methyl group (−CH3).

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  • An NIH shift is a chemical rearrangement where a hydrogen atom on an aromatic ring undergoes an intramolecular migration primarily during a hydroxylation reaction. This process is also known as a 1,2-hydride shift. These shifts are often studied and observed by isotopic labeling. An example of an NIH shift is shown below: In this example, a hydrogen atom has been isotopically labeled using deuterium (shown in red). As the hydroxylase adds a hydroxyl (the −OH group), the labeled site shifts one position around the aromatic ring relative to the stationary methyl group (−CH3). Several hydroxylase enzymes are believed to incorporate an NIH shift in their mechanism, including 4-hydroxyphenylpyruvate dioxygenase and the tetrahydrobiopterin dependent hydroxylases. The name NIH shift arises from the US National Institutes of Health from where studies first reported observing this transformation. (en)
  • NIH重排反应,或称NIH迁移(NIH shift) 芳环在羟基化或类似过程中,一个芳环氢原子发生的分子内迁移。也称1,2-负氢迁移。该现象一般通过同位素标记的方法观察到并进行研究。 上面的例子中一个芳环氢被氘原子(红)替换,底物中氘与甲基是处于对位的,最后产物中羟基与甲基处对位,而氘与甲基则处间位。 很多羟化酶的机理中包括NIH重排这一步骤,比如和依赖四氢生物蝶呤的羟化酶类。反应物也可以是卤代芳烃,反应中发生卤素原子的1,2-迁移,使原来卤素取代的位置转化为酚羟基。 此反应最早是由美国国立卫生研究院(缩写NIH)的研究者发现的,反应也因此得名。 (zh)
  • NIH-зсув (рос. NIH-сдвиг, англ. NIH shift) — внутрішньомолекулярна міграція атома Гідрогену, що супроводить молекулярне перегрупування ареноксидів у циклогексадієнони. Вважається, що це центральна стадія у ферментативному ароматичних циклів. NIH — скорочення від National Institute of Health (укр. Національний інститут охорони здоров'я США), де був відкритий зсув. (uk)
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  • NIH重排反应,或称NIH迁移(NIH shift) 芳环在羟基化或类似过程中,一个芳环氢原子发生的分子内迁移。也称1,2-负氢迁移。该现象一般通过同位素标记的方法观察到并进行研究。 上面的例子中一个芳环氢被氘原子(红)替换,底物中氘与甲基是处于对位的,最后产物中羟基与甲基处对位,而氘与甲基则处间位。 很多羟化酶的机理中包括NIH重排这一步骤,比如和依赖四氢生物蝶呤的羟化酶类。反应物也可以是卤代芳烃,反应中发生卤素原子的1,2-迁移,使原来卤素取代的位置转化为酚羟基。 此反应最早是由美国国立卫生研究院(缩写NIH)的研究者发现的,反应也因此得名。 (zh)
  • NIH-зсув (рос. NIH-сдвиг, англ. NIH shift) — внутрішньомолекулярна міграція атома Гідрогену, що супроводить молекулярне перегрупування ареноксидів у циклогексадієнони. Вважається, що це центральна стадія у ферментативному ароматичних циклів. NIH — скорочення від National Institute of Health (укр. Національний інститут охорони здоров'я США), де був відкритий зсув. (uk)
  • An NIH shift is a chemical rearrangement where a hydrogen atom on an aromatic ring undergoes an intramolecular migration primarily during a hydroxylation reaction. This process is also known as a 1,2-hydride shift. These shifts are often studied and observed by isotopic labeling. An example of an NIH shift is shown below: In this example, a hydrogen atom has been isotopically labeled using deuterium (shown in red). As the hydroxylase adds a hydroxyl (the −OH group), the labeled site shifts one position around the aromatic ring relative to the stationary methyl group (−CH3). (en)
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  • NIH shift (en)
  • NIH重排反应 (zh)
  • NIH-зсув (uk)
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