COMU: A third generation of uronium‐type coupling reagents |
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| Authors: | Ayman El‐Faham Fernando Albericio |
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| Affiliation: | 1. Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028‐Barcelona, Spain;2. Alexandria University, Faculty of Science, Department of Chemistry, P.O. Box 246 Ibrahimia, 21321 Alexandria, Egypt;3. King Saud University, Department of Chemistry, College of Science, P.O. Box 2455, 1451‐Riyadh, Kingdom of Saudi Arabia;4. CIBER‐BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028‐Barcelona, Spain;5. Department of Organic Chemistry, University of Barcelona, Martí i Franqués 1‐11, 08028‐Barcelona, Spain |
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| 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. Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd. |
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| Keywords: | coupling reagent uronium salt Oxyma peptide synthesis solid‐phase methodology |
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