COMU® features optimal properties as a peptide coupling reagent. In addition to its high and fast coupling efficiency, it shows very low or non-existent tendencies for racemization. COMU is a registered patent of Luxembourg Bio Technologies (No. 101784522/8,524,898).
COMU® is a registered patent of Luxembourg Bio Technologies Ltd., and we are the exclusive manufacturers.
CAS: 1075198-30-9
Synonym: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
Properties
Purity
≥98.0%
Molecular Formula
C12H19F6N4O4P
Molecular Weight
428.27 [gr/mol]
Appearance
White to off-white crystalline powder
Storage Conditions
Store in a cool and dry place (2-8oC)
Applications
- Epimerization during fragment coupling appears to be lessened with COMU than with HOBt or HATU.
- COMU is fully compatible with microwave-assisted peptide synthesis.
- COMU is very soluble in most commonly employed peptide coupling solvents, such as DMF or NMP, which makes it ideally suited for solid phase peptide synthesis.
- It is equally attractive for solution phase synthesis since by-products formed by COMU are water-soluble and can be separated by simple extraction.
- A color change during the reaction allows visual or colorimetric reaction monitoring.
- COMU can be used with nearly identical protocols that apply for common coupling reagents such as HBTU, TBTU, PyBOP, or HATU.
- It is considered the greener coupling reagent.
- It is used in some Canadian schools.
Studies
- A comparative study of amide-bond forming reagents in aqueous media – Substrate scope and reagent compatibility
Matthew Badland a, Robert Crook a, Bastien Delayre b, Steven J. Fussell a,⇑, Iain Gladwell a,
Michael Hawksworth a, Roger M. Howard c, Robert Walton a, Gerald A. Weisenburger c Tetrahedron Letters 58 (2017) 4391–4394 Read Article - Tandem deprotection/coupling for peptide synthesis in water at room temperature†
Margery Cortes-Clerget, a Jean-Yves Berthon,b Isabelle Krolikiewicz-Renimel,b
Laurent Chaisemartinb and Bruce H. Lipshutz *a Green Chem., 2017, 19, 4263 Read Article - Total Synthesis of Nannocystin Ax
Caroline Poock† and Markus Kalesse*,†,‡ Org. Lett. 2017, 19, 4536−4539 Read Article - Phenylglycine racemization in Fmoc-based solid-phase peptide
synthesis: Stereochemical stability is achieved by choice of reaction
conditions
Chen Liang, Mira A.M. Behnam, Tom R. Sundermann, Christian D. Klein ⇑ Tetrahedron Letters 58 (2017) 2325–2329 Read Article - Comparison of various coupling reagents in solid-phase aza-peptide synthesis
Meeli Arujõe, Anu Ploom ⇑, Anton Mastitski, Jaak Järv Tetrahedron Letters 58 (2017) 3421–3425 Read Article - COMU: A Safer and More Effective Replacement for Benzotriazole-Based Uronium Coupling Reagents. A. El-Faham, R. S. Funosas, R. Prohens, and F. Albericio Chem. Eur. J., 2009, 15, 9404–9416.
Read Article - COMU: A third generation of uronium-type coupling reagents
A. El-Faham and F. Albericio J. Pept. Sci. 2010, 16, 6–9.
Read Article - Microwave heating in solid-phase peptide synthesis
Tofteng, L. Malik, S. L. Pedersen, K. K. Sørensen, K. J. Jensen Chem. Soc. Rev., 2012, 41, 1826–1844.
Read Article - Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents
J. K. Twibanire and T. B. Grindley Org. Lett. 2011, 13, 12, 2988–2991.
Read Article - Tandem deprotection/coupling for peptide synthesis in water at room temperature.
Margery Cortes-Clerget, Jean-Yves Berthon, Isabelle Krolikiewicz-Renimel, Laurent Chaisemartinb and Bruce H. Lipshutz, Green Chem., 2017, 19,4263
Posters
A Non-Explosive Replacement for Benzotriazole Based Coupling Reagents
Ayman El-Faham, Ramon Subirós-Funosas, Fernando Albericio
View Poster