The DOI matches its Crossref record; 38 of the 38 references it cites were found in a registry or an index.
COMU: A Safer and More Effective Replacement for Benzotriazole‐Based Uronium Coupling Reagents
Abstract
We describe a new family of uronium‐type coupling reagents that differ in their iminium moieties and leaving groups. The presence of the morpholino group in conjunction with an oxime derivative—especially ethyl 2‐cyano‐2‐(hydroxyimino)acetate (Oxyma)—had a marked influence on the solubilities, stabilities, and reactivities of the reagents. Finally, the new uronium salt derived from Oxyma (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. COMU also showed a less hazardous safety profile than the benzotriazole‐based HDMA and HDMB, which exhibited unpredictable autocatalytic decompositions. Furthermore, the Oxyma moiety contained in COMU suggests a lower risk of explosion than in the case of the benzotriazole derivatives.
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Cites
Amide bond formation and peptide coupling
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1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive
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Methods and Protocols of Modern Solid Phase Peptide Synthesis
Amblard, M., Fehrentz, J.-A., Martinez, J., & Subra, G. (2006) · Molecular Biotechnology · doi:10.1385/mb:33:3:239 · Cited by 497
Subirós‐Funosas, R., Prohens, R., Barbas, R., El‐Faham, A., & Albericio, F. (2009) · Chemistry – A European Journal · doi:10.1002/chem.200900614 · Cited by 421
Self-citationCarpino, L. A., El-Faham, A., Minor, C. A., & Albericio, F. (1994) · Journal of the Chemical Society, Chemical Communications · doi:10.1039/c39940000201 · Cited by 353
Self-citationChemical Approaches to the Synthesis of Peptides and Proteins
Lloyd-Williams, P., Albericio, F., & Giralt, E. (2020) · CRC Press eBooks · doi:10.1201/9781003069225 · Cited by 334
Self-citationUse of Onium Salt-Based Coupling Reagents in Peptide Synthesis1
Albericio, F., Bofill, J. M., El-Faham, A., & Kates, S. A. (1998) · The Journal of Organic Chemistry · doi:10.1021/jo980807y · Cited by 276
Self-citationCarpino, L. A., & El-Faham, A. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00124a040 · Cited by 259
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Peptide Coupling Reagents, More than a Letter Soup
El-Faham, A., & Albericio, F. (2011) · Chemical Reviews · doi:10.1021/cr100048w · Cited by 1,245
Self-citationLarge-Scale Applications of Amide Coupling Reagents for the Synthesis of Pharmaceuticals
Dunetz, J. R., Magano, J., & Weisenburger, G. A. (2016) · Organic Process Research & Development · doi:10.1021/op500305s · Cited by 819
Peptide synthesis beyond DMF: THF and ACN as excellent and friendlier alternatives
Jad, Y. E., Acosta, G. A., Khattab, S. N., de la Torre, B. G., Govender, T., Kruger, H. G., El-Faham, A., & Albericio, F. (2015) · Organic & Biomolecular Chemistry · doi:10.1039/c4ob02046d · Cited by 92
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Metadata
- Authors
- El‐Faham, A., Funosas, R. S., Prohens, R., & Albericio, F.
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 2009-09-14
- Volume
- 15
- Issue
- 37
- Pages
- 9404-9416
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W1990173308
- Cited by
- 306
- References
- 38
- FWCI
- 5.40
- Type
- journal article
- Language
- en
- Open access
- closed
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