Oxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole-Based HOBt and HOAt with a Lower Risk of Explosion[1]
Oxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole-Based HOBt and HOAt with a Lower Risk of Explosion[1]
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DOI：
10.1002/chem.200900614
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发表时间：
2009-01-01
影响因子：
4.3
通讯作者：
Albericio, Fernando
中科院分区：
文献类型：
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作者：
Subiros-Funosas, Ramon;Prohens, Rafel;Albericio, Fernando
Oxyma [2-氰基-2-（羟基亚氨基）乙酸乙酯]已被测试为用于碳二亚胺方法中形成肽键的添加剂。它的性能有关的HOBt和HOAt，这是最近报道的表现出爆炸性能，报告。Oxyma显示出显著的抑制外消旋化的能力，以及在自动化和手动合成中令人印象深刻的偶联效率，其上级于HOBt的偶联效率，并且至少与HOAt的偶联效率相当，并且在更苛刻的肽模型中超过了后者的偶联剂。稳定性试验表明，在标准偶联条件下，不存在封端树脂的风险。最后，量热分析（DSC和ARC）显示，苯并三唑类添加剂的分解曲线与其报告的爆炸性一致，并表明Oxyma的爆炸风险较低。
Oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate] has been tested as an additive for use in the carbodiimide approach for formation of peptide bonds. Its performance in relation to those of HOBt and HOAt, which have recently been reported to exhibit explosive properties, is reported. Oxyma displayed a remarkable capacity to inhibit racemization, together with impressive coupling efficiency in both automated and manual synthesis, superior to those of HOBt and at least comparable to those of HOAt, and surpassing the latter coupling agent in the more demanding peptide models. Stability assays showed that there was no risk of capping the resin under standard coupling conditions. Finally, calorimetry assays (DSC and ARC) showed decomposition profiles for benzotriazole-based additives that were consistent with their reported explosivities and suggested a lower risk of explosion in the case of Oxyma.