COMU: A Safer and More Effective Replacement for Benzotriazole-Based Uronium Coupling Reagents

Author:

El-Faham Ayman,Funosas Ramon Subirós,Prohens Rafel,Albericio Fernando

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

Reference59 articles.

1. Abbreviations not defined in text: Aib, α-aminoisobutyric acid; DIEA, N,N-diisopropylethylamine; DMF, N,N-dimethylformamide; HOBt, 1-hydroxybenzotriazole; HOAt, 7-aza-1-hydroxybenzotriazole; N-HATU, N-[(dimethylamino)-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene)-N-methylmethanaminium hexafluorophosphate N-oxide; N-HBTU, N-[(1H-benzotriazol-1-yl)-(dimethylamino)methylene]N-methylmethanaminium hexafluorophosphate N-oxide; DMCH,4-((dimethyamino)chloromethylene)morpholin-4-Iminium hexaflurophosphate HDMA, 1-((dimethylimino)morpholino>methyl)3-H-[1,2,3]triazolo[4,5-b]pyridine-1–3-olate hexafluorophosphate; HDMB, 1-((dimethylimino)morpholino>methyl)3-H-benzo[1,2,3]triazolo-1-ium-3-olate hexafluorophosphate; 6-HDMCB, 1-((dimethylimino)morpholino>methyl)3-H-6-chlorobenzo[1,2,3] triazolo-1-ium-3-olate hexafluorophosphate; DMU, N,N-dimethylmorpholine-4-carboxamide; DmPyU, N,N-Dimethylpiperidine-1-carboxamide; MPyU, Morpholino(pyrrolidin-1-yl)methanone; N-DmPyCH, (Chloro(pyrrolidin-1-yl)methylene)-N-methylmethanaminium hexafluorophosphate; MPyCH, 1-(chloro(morpholino)methylene)pyrrolidinium Hexafluorophosphate; HOTU, O-[Cyano(ethoxycarbonyl)methylidene)amino]-1,1,3,3-tetramethyluronium Hexafluorophosphate; HdmPyOC, 1-[(1-(Cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylamino-pyrrolodinomethylene)] methanaminium Hexafluorophosphate; COMU, 1-[(1-(Cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylamino-morpholinomethylene)] methanaminium Hexafluorophosphate; HMPyOC, 1-((1-cyano-2-ethoxy-2-oxoethylideneaminooxy)(morpholino)methylene) pyrrolidinium Hexafluorophosphate; HTODC, O-[(Dicyanomethylidene)amino]-1,1,3,3-tetramethyluronium Hexafluorophosphate; HDmPyODC, 1-[(1-(dicyanomethylideneaminoxy)-dimethylamino-pyrrolodinomethylene)] methanaminium Hexafluorophosphate; HDMODC, 1-[(1-(dicyanomethyleneaminooxy)-dimethylamino-morpholinomethylene)] methanaminium Hexafluorophosphate HMPyODC, 1-((dicyanomethyleneaminooxy)morpholinomethylene)pyrrolidinium Hexafluorophosphoate; HTODeC, O-[(diethoxycarbonylmethylidene)amino]-1,1,3,3-tetramethyluronium Hexafluorophosphate; HDMODeC, 1-[(1,3-diethyoxy-1,3-dioxopropan-2-ylideneaminooxy)-dimethylamino-morpholinomethylene)] methanaminium Hexafluorophosphate; HTOPC, N-[(cyano(pyridine-2-yl)methyleneaminooxy)(dimethylamino)methylene)-N-Methylmethanaminium Hexafluorophosphate; HDMOPC, N-[(cyano(pyridine-2-yl)methyleneaminooxy)(dimethylamino)methylene)-N-morpholinomethanaminium Hexafluorophosphate; HMPyA, 1-(morpholino(pyrrolidinium-1-ylidene)methyl)-1H-[1,2,3]triazolo[4,5-I]pyridine 3-oxide Hexafluorophospahte; HMPyB, 1-(morpholino(pyrrolidinium-1-ylidene)methyl)-1H-benzo[d][1,2,3]triazole 3-oxide Hexafluorophosphate; HMPyC, 5-chloro-1-(morpholino(pyrrolidinium-1-ylidene)methyl)-1H-benzo[d][1,2,3]triazole 3-oxide hexafluorophosphate; Amino acids and peptides are abbreviated and designated following the rules of the IUPAC-IUB Commission of Biochemical Nomenclature [J. Biol. Chem. 247, 977 (1972)].

2. Synthesis of Peptides and Peptidomimetics, Houben-Weyl, Methods of Organic Chemistry, Vol. E22a (Ed.: M. Goodman), Thieme, Stuttgart, 2002;

3. Methods and Protocols of Modern Solid Phase Peptide Synthesis

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