J Pept Sci. 2010 Jan;16(1):6-9.

COMU: a third generation of uronium-type coupling reagents.

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Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain. aymanel_faham@hotmail.com

Abstract

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.

PMID:: 19950108; [PubMed - indexed for MEDLINE]

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COMU: a safer and more effective replacement for benzotriazole-based uronium coupling reagents. [Chemistry. 2009]
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