COMU: A safer and more effective replacement for benzotriazole-based uronium coupling reagents

Chemistry - A European Journal

Volumn 15, Issue 37, 2009, Pages 9404-9416

  El Faham, Ayman ^a,b,c   Funosas, Ramon Subirós ^a,d   Prohens, Rafel ^d   Albericio, Fernando ^a,d  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c Alexandria University Faculty Of Science   (Egypt)

^d UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Coupling reagents oxyma; Peptides; Solid phase synthesis; Uronium salts

Indexed keywords

AUTOCATALYTIC DECOMPOSITIONS; BENZOTRIAZOLE DERIVATIVE; BENZOTRIAZOLES; COUPLING REAGENTS; COUPLING REAGENTS OXYMA; HYDROGEN BOND ACCEPTORS; IMINIUM; LEAVING GROUPS; RISK OF EXPLOSIONS; SOLID-PHASE SYNTHESIS; URONIUM SALTS;

AMINES; HYDROGEN; HYDROGEN BONDS; SALTS;

PEPTIDES;

(1 (CYANO 2 ETHOXY 2 OXOETHYLIDENEAMINOOXY) DIMETHYLAMINO MORPHOLINOMETHYLENE)]METHANAMINIUM HEXAFLUOROPHOSPHATE; (1-(CYANO-2-ETHOXY-2-OXOETHYLIDENEAMINOOXY)-DIMETHYLAMINO-MORPHOLINOMETHYLENE)]METHANAMINIUM HEXAFLUOROPHOSPHATE; 1 HYDROXY 7 AZABENZOTRIAZOLE; 1 HYDROXYBENZOTRIAZOLE; 1-HYDROXY-7-AZABENZOTRIAZOLE; 1-HYDROXYBENZOTRIAZOLE; BENZOTRIAZOLE; DIGOXIGENIN; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; MORPHOLINE DERIVATIVE; N HYDROXYSUCCINIMIDYL DIGOXIGENIN 3 O METHYLCARBONYL EPSILON AMINOCAPROATE; N-HYDROXYSUCCINIMIDYL DIGOXIGENIN-3-O-METHYLCARBONYL-EPSILON-AMINOCAPROATE; ORGANOPHOSPHORUS COMPOUND; OXYMA; PEPTIDE; PREGNANE DERIVATIVE; SUCCINIMIDE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZA COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; DIGOXIGENIN; MOLECULAR CONFORMATION; MORPHOLINES; ORGANOPHOSPHORUS COMPOUNDS; PEPTIDES; PREGNADIENES; SUCCINIMIDES; TRIAZOLES;

EID: 70349277032     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900615     Document Type: Article

References (52)

1. Abbreviations not defined in text: Aib, a-aminoisobutyric acid; DIEA, N,N-diisopropylethylamine; DMF, N,N-dimethylformamide; HOBt, 1-hydroxybenzotriazole; HOAt, 7-aza-l-hydroxybenzotriazole; N-HATU, N-[(dimethylamino)-lH-l,2,3-triazolo[4,5-b]pyridinl-yl-methylene) -N-methylmethanaminium hexafluorophosphate Noxide; N-HBTU, N-[(lH-benzotriazol- l-yl)-(dimethylamino)methylene]N-methylmethanaminium hexafluorophosphate N-oxide; DMCH,4-((dimethyamino)chloromethylene)morpholin-4-Iminium hexaflurophosphate HDMA, l-((dimethylimino)morpholino > methyl)3-H-[l,2,3] triazolo[4,5-b]pyridine-l-3-olate hexafluorophosphate; HDMB, l-((dimethylimino)morpholino>methyl)3-H-benzo[l,2,3]triazolo-l-ium-3-olate hexafluorophosphate; 6-HDMCB, 1((dimethylimino)morpholino > methyl)3-H-6-chlorobenzo[1,2,3] triazolo-l-ium-3-olate hexafluorophosphate; DMU, N,N-dimethylmorpholine-4-carboxamide; DmPyU, N,N-Dimethylpiperidine-l- carboxamide; MPyU, Morpholino(pyrrolidin-l-yl)methanone; NDmPyCH, (Chloro(pyrrolidin-l-yl)methylene)-N-methylmethanaminium hexafluorophosphate; MPyCH, l-(chloro(morpholino)methylene)pyrrolidinium Hexafluorophosphate; HOTU, O-[Cyano(ethoxycarbonyl)methylidene)amino]-l,l,3,3-tetramethyluronium Hexafluorophosphate; HdmPyOC, l-[(l-(Cyano-2-ethoxy-2-oxoethylideneaminooxy)- dimethylamino-pyrrolodinomethylene)] methanaminium Hexafluorophosphate; COMU, l-[(l-(Cyano-2-ethoxy-2oxoethylideneaminooxy)-dimethylamino-morpholinomethylene) ] methanaminium Hexafluorophosphate; HMPyOC, l-((l-cyano-2ethoxy-2- oxoethylideneaminooxy)(morpholino)methylene) pyrrolidinium Hexafluorophosphate; HTODC, O-[(Dicyanomethylidene)amino]-l,l,3,3-tetramethyluronium Hexafluorophosphate; HDmPyODC, l-[(l-(dicyanomethylideneaminoxy)- dimethylaminopyrrolodinomethylene)] methanaminium Hexafluorophosphate; HDMODC, l-[(l-(dicyanomethyleneaminooxy)-dimethylaminomorpholinomethylene)] methanaminium Hexafluorophosphate HMPyODC, l-((dicyanomethyleneaminooxy) morpholinomethylene)pyrrolidinium Hexafluorophosphoate; HTODeC, O-[(diethoxycarbonylmethylidene)amino]-l,l,3,3-tetramethyluronium Hexafluorophosphate; HDMODeC, l-[(l,3-diethyoxy-l,3-dioxopropan-2- ylideneaminooxy)-dimethylamino-morpholinomethylene)] methanaminium Hexafluorophosphate; HTOPC, N-[(cyano(pyridine-2-yl)methyleneaminooxy) (dimethylamino)methylene)-N-Methylmethanaminium Hexafluorophosphate; HDMOPC, N-[(cyano(pyridine-2yl)methyleneaminooxy)(dimethylamino)methylene) -N-morpholinomethanaminium Hexafluorophosphate; HMPyA, l- (morpholino(pyrrolidinium-l-ylidene)methyl)-2H-[l,2,3]triazolo[4,5-I]pyridine 3oxide Hexafluorophospahte; HMPyB, l-(morpholino(pyrrolidinium1-ylidene)methy1)- 1H-benzo[d][1,2,3]triazole 3-oxide Hexafluorophosphate; HMPyC, 5-chloro-l-(morpholino(pyrrolidinium-l-ylidene)methy1)-1H-benzo[d][1,23] 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. a) P. Lloyd-Williams, F. Albericio, E. Giralt, Chemical Approaches to the Synthesis of Peptides and Proteins, CRC, Boca Raton, 1997;
3. b) Synthesis of Peptides and Peptidomimetics, Houben-Weyl, Methods of Organic Chemistry, Vol.E22a (Ed.: M. Goodman), Thieme, Stuttgart, 2002;
4. (c) M. Amblard, J.-A. Fehrentz, J. Martinez, G. Subra, Mol. Biotechnol. 2006, 33, 239-254.
5. a) F. Albericio, L. A. Carpino in Methods in Enzymology, SolidPhase Peptide Synthesis, Vol.289 (Ed.: G.B. Fields), Academic Press, Orlando, 1997, pp. 104-126;
6. b) J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243-2266;
7. Z.J. Kaminski, Biopolymers 2000, 55, 140-165;
8. (d) F. Albericio, R. Chinchilla, D. J. Dodsworth, C. Najera, Org. Prep. Proced. Int. 2001, 33, 203-303;
9. e) S-Y Han, Y-A. Kim, Tetrahedron 2004, 60, 2447-2467;
10. f)C.A.G.N. Montalbetti, V. Falque, Tetrahedron 2005, 61,10827-10852.
11. V. Dourtoglou, J. C. Ziegler, B. Gross, Tetrahedron Lett. 1978,1269-1272.
12. F. Albericio, J. M. Bofill, A. El-Faham, S. A. Kates, J. Org. Chem. 1998, 63, 9678-9683.
13. a) P. Henklein, M. Beyermann, M. Bienert, R. Knorr, in Proceedings of the 21st European Peptide Symposium (Eds.: E. Giralt, D. Andreu), Escom Sience, Leiden, 1991, pp. 67-68.
14. b) R. Knorr, A. Trzeciak, W. Bannwarth, D. Gillessen in Peptide, Proceedings of the European Peptide Symposium (Eds.: G. Jung, E. Bayer), de Gruyter, Berlin, 1989, pp. 37-39;
15. L.A. Carpino, J. Am. Chem. Soc. 1993, 115, 4397-4398;
16. (c) L. A. Carpino, A. El-Faham, C. A. Minor, F. Albericio, J. Chem. Soc. Chem.Comm 1994, 201-203;
17. e)J. C. H. M. Wijkmans, J. A. W. Kruijtzer, G. A. van der Marel, J. H. van Boom, W. Bloemhoff, Reel. Trav. Chim. Pays-Bas 1994, 113, 394-397;
18. f) L. A. Carpino, A. El-Faham, F. Albericio, J. Org. Chem. 1995, 60, 3561-3564;
19. g) L. A. Carpino, A. El-Faham, J. Am Chem. Soc. 1995, 117, 5401-5402;
20. h) A. El-Faham, Chem. Lett. 1998, 671-672;
21. (i) J. Habermann, H. Kunz, J. Prakt. Chem. 1998, 340, 233-239;
22. j) P. Gamer, J. T. Anderson, S. Dey, W. J. Youngs, K. Galat, J. Org. Chem. 1998, 63, 5732-5733;
23. k)M.A. Bailén, R. Chinchilla, D. J. Dodsworth, C. Najera, J. Org. Chem. 1999, 64, 8936-8939;
24. A. ElFaham, Lett. Pept. Sci. 2000, 7, 113-121;
25. (l) F. Albericio, M. A. Bailen, R. Chinchilla, J. D. Dodsworth, C. Najera, Tetrahedron 2001, 57, 9607-9613;
26. n) O. Marder, Y. Shvo, F. Albericio, Chim. Oggi 2002, 20, 37-41;
27. o) M. Vendrell, R. Ventura, A. Ewenson, M. Royo, F. Albericio, Tetrahedron Lett. 2005, 46, 5383-5386.
28. a) A. El-Faham, F. Albericio, Org. Lett. 2007, 9, 4475-4477;
29. b) A. El-Faham, F. Albericio, J. Org. Chem. 2008, 73, 2731-2737.
30. I. Abdelmoty, F. Albericio, L. A. Carpino, B. F. Foxman, S. A. Kates, Lett. Peptide Sci. 1994, 1, 57-67.
31. a) L. A. Carpino, H. Imazumi, A. El-Faham, F. J. Ferrer, C. Zhang, Y. Lee, B. M. Foxman, P. Henklein, C. Hanay, C. Mügge, H. Wenschuh, J. Klose, M. Beyermann, M. Bienert, Angew. Chem. 2002, 114, 457-461;
32. Angew. Chem. Int. Ed. 2002, 41, 441-445.
33. K. D. Wehrstedt, P. A. Wandrey, D. Heitkamp, J. Hazard. Mater. 2005,126, 1-7.
34. R. Subirós-Funosas, R. Prohens, R. Barbas, A. El-Faham, F. Albericio, Chem. Eur. J. 2009, 15, 9394-9403.
35. G. Breipohl, W. Koenig, Ger. Offen. DE 90-4016596, 1991.
36. L. A. Carpino, P. Henklein, B. M. Foxman, I. Abdelmoty, B. Costisella, V. Wray, T. Domke, A. El-Faham, C. J. Mugge, Org. Chem. 2001, 66, 5245-5247.
37. R. King, R. Hirst, Safety in the Process Industries, 2nd ed., Elsevier, Oxford, 2002.
38. J. Steinbach, Safety Assessment for Chemical Processes, Wiley-VCH, Weinheim, 1999, pp. 29-46.
39. F. Stoessel, Thermal Safety of Chemical Processes, Wiley-VCH, Weinheim, 2008, 311-334.
40. I. Townsend, J. Therm. Anal. 1991, 37, 2031-2066.
41. a)F. Stoessel, Chem. Eng. Prog. 1993, 89, 68-75;
42. b)F. Stoessel, H. Fierz, P. Lerena, G. Kille, Org. Prep. Proced. Int. 1997, 1, 428-434.
43. a) T. C. Hofelich, R. C. Thomas, Int. Symp. Runaway React. 1989, 74-85;
44. b) J. Singh, C. Simms, Inst. Chem. Eng. Symp. Ser. 2001,148, 67-79.
45. J. Barton, R. Rogers, Chemical Reaction Hazards, 2nd ed., Institution of Chemical Engeneers, Rugby (UK), 1997.
46. M. Kitamura, S. Chiba, K. Narasaka, Bull. Chem. Soc. Jpn. 2003, 76, 1063-1070.
47. K. N. F. Shaw, C. Nolan, J. Org. Chem. 1957, 22, 1668-1670.
48. J. Izdebski, Pol. J. Chem. 1979, 53, 1049-1057.
49. A. El-Faham, S. N. Khattab, M. Abdul-Ghani, F. Albericio, Eur. J. Org. Chem. 2006,1563.
50. P. F. Wiley, Hsiung Verónica, Spectrochim. Acta Part A 1970, 26, 1119-1130.
51. A. El-Faham, Org. Prep. Proced. 1998, 30, 477-481.
52. B. Roduit, W. Dermaut, A. Lungui, P. Folly, B. Berger, A. Sarbach, J. Therm. Anal. 2008, 93,163.