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COMU: a third generation of uronium-type coupling reagents.
Journal of Peptide Science ( IF 1.8 ) Pub Date : 2009-11-30 , DOI: 10.1002/psc.1204
Ayman El-Faham 1 , Fernando Albericio
Affiliation  

COMU is a third generation of uronium‐type coupling reagent based on ethyl 2‐cyano‐2‐(hydroxyimino)acetate (Oxyma) as well as a morpholino carbon skeleton. The presence of the morpholino group has a marked influence on the solubility, stability and reactivity of the reagent. COMU performed extremely well in the presence of only 1 equiv. of base, thereby confirming the effect of the hydrogen bond acceptor in the reaction. The by‐products of COMU are water soluble and easily removed, making it an excellent choice of coupling reagent for solution‐phase peptide synthesis. Finally, COMU shows a less hazardous safety profile than benzotriazole‐based reagents, such as HATU and HBTU, which in addition exhibit unpredictable autocatalytic decompositions and therefore a higher risk of explosion. Furthermore, in contrast to benzotriazole‐based reagents, COMU is significantly less likely to cause allergic reaction. Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd.

中文翻译:

COMU:第三代铀型偶联剂。

COMU是基于2-氰基-2-(羟基亚氨基)乙酸乙酯(Oxyma)和吗啉代碳骨架的第三代铀型偶联剂。吗啉代基团的存在对试剂的溶解度,稳定性和反应性具有显着影响。在只有1个当量的情况下,COMU的表现非常出色。因此,证实了氢键受体在反应中的作用。COMU的副产物是水溶性的,很容易去除,使其成为溶液相肽合成的偶联剂的绝佳选择。最后,COMU与基于苯并三唑的试剂(例如HATU和HBTU)相比,显示出较低的危险安全性,此外,后者还具有不可预测的自催化分解作用,因此爆炸风险更高。此外,与基于苯并三唑的试剂相比,COMU引起过敏反应的可能性大大降低。版权所有©2009欧洲多肽协会和John Wiley&Sons,Ltd.。
更新日期:2009-11-30
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