Cyclization of all-L-pentapeptides by means of 1-hydroxy-7-azabenzotriazole-derived uronium and phosphonium reagents

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8831-8838

  Ehrlich, Angelika ^a,c   Heyne, Hans Ulrich ^b   Winter, Rüdiger ^b   Beyermann, Michael ^a   Haber, Hanka ^b   Carpino, Louis A ^a   Bienert, Michael ^b  

^a LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^b UNIVERSITY OF MASSACHUSETTS   (United States)

^c UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE;

ARTICLE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0030470879     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951108d     Document Type: Article

References (40)

1. Dale, J. Angew. Chem. 1966, 78, 1070.
2. Kessler, H.; Kutscher, B. Liebigs Ann. Chem. 1986, 869.
3. Kessler, H.; Kutscher, B. Liebigs Ann. Chem. 1986, 914.
4. Kopple, K. D. J. Pharm. Sei. 1972, 61, 1345.
5. Izumiya, N.; Kato, T.; Waki, M. Biopolymers 1981, 20,1785.
6. Brady, S. F.; Paleveda, W. J.; Arison, B. H.; Freidinger, R. M.; Nutt, R. F.; Veber, D. F. In Peptides. Structure and Function. Proceedings of the 8th American Peptide Symposium; Hruby, V. J., Rich, D. H., Eds.; Pierce Chemical Company: Rockford, 1983; p 127.
7. Abbreviations: AcOH, acetic acid; AcHmb, 2-acetoxy-4-methoxybenzyl; BOP, (l-benzotriazolyloxy)tris(dimethylamino)phosphonium hexafluorophosphate; DCC, dicyclohexylcarbodiimide; DCM, dichloromethane; DIEA, diisopropylethylamine; DMF, dimethylformamide; DPPA, diphenylphosphoryl azide; Hmb, 2-hydroxy-4-methoxybenzyl; HOBt, 1-hydroxybenzotriazole; HOAt, l-hydroxy-7-azabenzotriazole; HAPyU, O-(7-azabenzotriazol-l-ylH,l,3,3-bis(tetramethylene)uronium hexafluorophosphate; HATU, Af-[(dimethylamino)-H-l,2,3-triazolo[4,5-6]pyridin-l-yl-methylene]-J/- methylmethanaminium hexafluorophosphate; PyAOP, (7-azabenzotriazol-l-yIoxy)trispyrrolidinophosphonium hexafluorophosphate; PyBOP, (benzotriazol-l-yloxy)trispyrrolidinophosphonium hexafluorophosphate; TAPipU, O-(7-azabenzotriazol-lyl)-l,l,3,3-pentamethylenuronium tetrafluoroborate; TBPipU, O-(benzotriazol-l-ylH,l,3,3-pentamethyIenuronium tetrafluoroborate; TBTU, O-(benzotriazol-l-yD-l,l,3,3-tetramethyluronium tetrafluoroborate; TFA, trifluoracetic acid; TFE, trifluoroethanol; TOPPipU, 2-(2-oxopyrid-lyl)-l,l,3,3-pentamethylenuronium tetrafluoroborate.
8. Schmidt, R.; Neubert, K. Int. J. Peptide Protein Res. 1991, 37, 502.
9. Heavner, G. A.; Audhya, T.; Doyle, D.; Tjoeng, F. S.; Goldstein, G. Int. J. Peptide Protein Res. 1991, 37,198.
10. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989,30,1927.
11. Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975,14, 1219.
12. (a) Felix, A. M.; Wang, Ch.-T.; Heimer E. P.; Fournier, A. Int. J. Peptide Protein Res. 1988,31,231-238.
13. (b) Zimmer, S.; Hoffmann, E.; Jung, G.; Kessler, H. In Peptides 1992. Proceedings of the 22nd European Peptide Symposium; Schneider, C. H., Eberle A. N., Eds.; ESCOM: Leiden, 1993; p 393.
14. Benoiton, N. L.; Lee, Y. C.; Steinauer, R.; Chen, F. M. F. Int. J. Peptide Protein Res. 1992, 40, 559.
15. Recently, X-ray analysis15 has shown that HATU crystallizes as the guanidinium salt shown in Figure 1 rather than as of the isomeric O-substituted form i previously assigned to this compound. HBTU ii was also shown to crystallize in guanidinium rather than the uronium form. For analogous coupling reagents (HAPyU, TAPipU, TBPipU, TBTU) for which X-ray data have not yet been obtained the traditional structural representations and nomenclature have arbitrarily been retained in the present communication. To date there is no evidence concerning the possibility of equilibration in solution between the O- and N-forms of these compounds. fr\ fr v-PF? sjy PF Oo QO C(NMej)2 !
16. Abdelmoty, L; Albericio, F.; Carpino, L. A.; Foxman, B. M.; Kates, S. A. Lett. Pept. Sei. 1994,1, 57.
17. (a) Azev, Y.; Mokrushina, G. A.; Postovoskii, I. Ya.; Sheinker, Yu. N.; Anisimova, O. S. Chem. Heterocycl. Compd. 1976, 1172.
18. (b) Mokrushina, G. A.; Azev, Y.; Postovoskii, I. Ya. Chem. Heterocycl. Compd. 1975,880.
19. Azev, Y.; Mokrushina, G. A.; Postovoskii, I. Ya. Chem. Heterocycl. Compd. 1974, 687.
20. Sacher, R. M.; Alt, G. H.; Darlington, W. A. J. Agric. Food Chem. 1973, 21, 132.
21. (a) Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397.
22. (b) Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201.
23. Ehrlich, A.; Rothemund, S.; Brudel, M.; Beyermann, M.; Carpino, L. A.; Bienert, M. Tetrahedron Lett. 1993,34, 4781.
24. Henklein, P.; Beyermann, M.; Bienert, M.; Knorr, R. In Peptides 1990, Proceedings of the 21st European Peptide Symposium; Giralt, E., Andreu, D., Eds.; ESCOM: Leiden, 1991; p 67.
25. The cyclization of various penta- and hexapeptides via HBTU was recently described (ref 21) as yielding 2-21 of the cyclopeptides after reaction times of 2-16 h. The stereochemical integrity of the activated araino acid residues was not discussed. Considering our results with TBTU (Figures 5 and 6; Table 1), it would be expected that considerable C-terminal epimerization would also occur in the case of HBTU.
26. Sowemimo, V.; Scanlon, D.; Jones, P.; Craik, D. J. J, Protein Chem. 1994,13, 339.
27. It is expected that the use of HOAt-derived coupling reagents would also improve the cyelization of resin-bound peptides. In fact, HATU was found to give better results than BOP in the final head-to-tail cyclization of a resin-bound pentapeptide library constructed in four variable positions from glycine, proline, arginine, and three nonspecified amino acids.23 Similarly, in side-chain to side-chain cyclizations HAPyU and HATU gave far better yields of the desired cyclic peptides than HBTU. However, in contrast to peptide cyclization in solution as described in the present communication, HATU-, HAPyU-, and HBTU-mediated cyclizations of resin-bound peptides are reported to be accompanied by significant amounts of alkylguanidinium peptides formed by reaction of the uronium reagent with the free amino group.24
28. Darlak, K.; Romanovskis, P.; Spatola, A. F. In Peptides, Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium 1993 Hodges, R. S., Smith, J. A., Eds.; ESCOM: Leiden, 1994; p 981.
29. Story, S. C.; Aldrich, J. V. Int. J. Peptide Protein Res. 1994,43, 292.
30. Arttamanykul, S.; Leelasvatanakij, L.; Aldrich, J. V. 23rd Eur. Pept. Symp., Braga, Portugal, 1994, poster P76.
31. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Peptides 1990, Proceedings of the 21st European Peptide Symposium; Girald, E., Andrew, D., Eds.; ESCOM: Leiden, 1991; p 62.
32. (a) Carpino, L. A.; El-Faham, A. J. Org. Chem. 1994, 59, 695.
33. (b) Carpino, L. A.; El-Faham, A.; Albericio, F. Tetrahedron Lett. 1994, 35, 2279.
34. Feiertag, S.; Wiesmüller, K.-H.; Nicholson, G. J.; Jung, G. In Peptides: Chemistry, Structure and Biology, Proceedings of the 14th American Peptide Symposium 1995 Kaumaya, P. T. P., Hodges, R. S., Eds.; ESCOM: Leiden, 1996, in press.
35. Blaakmeer, J.; Tijsse-Klasen, T.; Tesser, G. I. Int. J. Peptide Protein Res. 1991, 37, 556.
36. Johnson, T.; Quibell, M. Tetrahedron Lett. 1994, 35, 463.
37. Quibell, M.; Turnell, W. G.; Johnson, T. Tetrahedron Lett. 1994, 35, 2237.
38. Cavelier-Frontin, F.; Achmad, S.; Verducci, J.; Jacquier, R. J. Mol. Struct. 1993, 286, 125.
39. Kusomoto.S.; Matsukura, M.; Shiba, T. Biopolymers 1981,20, 1869.
40. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970 34, 595.