Ethyl 2-Cyano-2-(hydroxyimino)acetate (Oxyma): An Efficient and Convenient Additive Used with Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) to Replace 1-Hydroxybenzotriazole (HOBt) and 1-Hydroxy-7-azabenzotriazole (HOAt) during Peptide Synthesis
Ethyl 2-Cyano-2-(hydroxyimino)acetate (Oxyma): An Efficient and Convenient Additive Used with Tetramethylfluoroformamidinium Hexafluorophosphate (TFFH) to Replace 1-Hydroxybenzotriazole (HOBt) and 1-Hydroxy-7-azabenzotriazole (HOAt) during Peptide Synthesis
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DOI：
10.1246/bcsj.20100075
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发表时间：
2010-11-15
影响因子：
4
通讯作者：
Khattab, Sherine N.
中科院分区：
文献类型：
--
作者：
Khattab, Sherine N.
讨论了2-氰基-2-羟亚氨基乙酸乙酯(Oxyma)作为苯并三氮唑类添加剂的替代物在TFFH合成多肽方法中的适宜性，包括它的外消旋控制能力，以及它在困难偶联中的偶联效率，无论是溶液偶联还是固相偶联中的分段偶联。此外，还研究了基于Boc的溶液相肽的合成及其在生长的多肽链存在下的稳定性。Oxyma在消旋抑制方面表现出显著的效果，同时在溶液合成和固相合成中都表现出令人印象深刻的耦合效率。此外，Oxyma比HOBt和Hoat的爆炸风险更低。
The appropriateness of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) as a substitute for benzotriazole-based additives, for use in the TFFH approach for peptide synthesis, is discussed in terms of its capacity to control racemization, its coupling efficiency in difficult couplings either for stepwise or segment coupling in solution- and solid-phase coupling. In addition, Boc-based solution-phase peptide synthesis and its stability in the presence of growing peptide chains were studied. Oxyma displayed remarkable results in terms of racemization depression together with impressive coupling efficiency in both solution- and solid-phase synthesis. Furthermore, Oxyma suggests a lower risk of explosion than HOBt and HOAt.