A coupling reagent for peptide synthesis whose coupling efficiency in solid and liquid phase peptide coupling is superior to HOBt, and at least comparable to HOAt 1. Has a remarkable capacity to inhibit racemization as an additive in carbodiimide mediated amide bond formation 2. Also used in resin-to-resin acyl- and aminoacyl-transfer reactions as oxime supports 3.
Advantages of ethyl (hydroxyimino)cyanoacetate include 2: non-explosive replacement for HOBt and HOAt;outperforms HOAt in sterically demanding peptide bond formation;suitable for carbodiimide mediated peptide coupling; less epimerization than HOBt in fragment condensation reactions.
1. Chem.–Eur. J. 2009, 15, 9394
2. Chem.–Eur. J. 2009, 15, 9404
3. J. Am. Chem. Soc.1999, 121, 1636