COMU: a third generation of uronium-type coupling reagents.
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.
El-Faham
Ayman
A
Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain. aymanel_faham@hotmail.com
Albericio
Fernando
F
D000085:Acetates / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D009025:Morpholines / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010091:Oximes / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis; D012996:Solutions
C000593117:1-((1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylaminomorpholinomethylene))methanaminium; D000085:Acetates; D007097:Imines; D007202:Indicators and Reagents; D009025:Morpholines; D010091:Oximes; D010455:Peptides; D012996:Solutions; C548311:ethyl 2-cyano-2-(hydroxyimino)acetate