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Fmoc-Amox, A Suitable Reagent for the Introduction of Fmoc
Organic Process Research & Development ( IF 3.4 ) Pub Date : 2017-08-24 00:00:00 , DOI: 10.1021/acs.oprd.7b00199
Ashish Kumar , Anamika Sharma , Elvira Haimov 1 , Ayman El-Faham 2, 3 , Beatriz G. de la Torre , Fernando Albericio 3, 4
Affiliation  

Synthesis of most peptides is achieved using solid-phase peptide synthesis employing the Fmoc/tert-butyl strategy. However, the introduction of Fmoc in N-unprotected amino acids seems to be challenging due to the formation of dipeptides and sometimes tripeptides as impurities and β-alanyl impurities when Fmoc-OSu is used as well. Herein, we report an efficient and successful method using Fmoc-Amox, which is an oxime based derivative, toward the synthesis of Fmoc-glycine with no traces of side reactions. Fmoc-Amox is inexpensive, and Amox can be easily removed after the reaction, thus affording pure Fmoc-Gly-OH devoid of any detrimental impurities or contamination, mainly dipeptide or Amox itself, as shown by high-performance liquid chromatography and NMR, respectively.

中文翻译:

Fmoc-Amox,适合引入Fmoc的试剂

使用Fmoc /丁基策略的固相肽合成可以实现大多数肽的合成。但是,由于在使用Fmoc-OSu时会形成二肽,有时还会形成三肽作为杂质和β-丙氨酸杂质,因此在N-未保护的氨基酸中引入Fmoc似乎具有挑战性。在本文中,我们报告了一种有效且成功的方法,该方法使用Fmoc-Amox(一种基于肟的衍生物)来合成Fmoc-甘氨酸,而没有任何副反应的痕迹。Fmoc-Amox价格便宜,而且反应后可轻松去除Amox,从而提供纯净的Fmoc-Gly-OH,不含任何有害杂质或污染物,主要是二肽或Amox本身,分别由高效液相色谱和NMR显示。
更新日期:2017-08-25
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