Synthesis of asymmetrized 2-benzyl-1,3-diaminopropane by a chemoenzymatic route: A tool for combinatorially developing peptidomimetics

Tetrahedron Asymmetry

Volumn 10, Issue 18, 1999, Pages 3571-3592

  Banfi, Luca ^a   Guanti, Giuseppe ^a   Riva, Renata ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZYL 1,3 DIAMINOPROPANE; CARBAMIC ACID; DIPEPTIDE; PROPANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG HYDROLYSIS; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL;

EID: 0033405533     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00371-7     Document Type: Article

References (57)

1. Clary, L.; Santaella, C.; Vierling, P. Tetrahedron 1995, 51, 13073-13088.
2. Jacobson, A. R.; Gintzler, A. R.; Sayre, L. M. J. Med. Chem. 1989, 32, 1708-1717.
3. Stepinski, J.; Tam, S. W. Z. Naturforsch. 1994, 49b, 407-411.
4. Lambert, D. M.; Neuvens, L.; Mergen, F.; Gallez, B.; Poupaert, J. H.; Ghysel-Burton, J.; Maloteaux, J.-M.; Dumont, P. J. Pharm. Pharmacol. 1993, 45, 186-191.
5. Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720.
6. Martin, J. A.; Redshaw, S.; Thomas, G. J. Progress in Medicinal Chemistry 1995, 32, 239-287.
7. Wonacott, A.; Cooke, R.; Hayes, F. R.; Hann, M. M.; Jhoti, H.; McMeekin, P.; Mistry, A.; Murray-Rust, P.; Singh, O. M. P.; Weir, M. P. J. Med. Chem. 1993, 36, 3113-3119.
8. Haque, T. S.; Skillman, A. G.; Lee, C. E.; Habashita, H.; Gluzman, I. Y.; Ewing, T. J. A.; Goldberg, D. E.; Kuntz, I. D.; Ellman, J. A. J. Med. Chem. 1999, 42, 1428-1440.
9. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
10. Banfi, L.; Guanti, G.; Mugnoli, A.; Riva, R. Tetrahedron: Asymmetry 1998, 9, 2481-2492, and references cited therein.
11. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. Tetrahedron Organic Chemistry Series; Elsevier Science: Oxford, 1994.
12. Adamczyk, M.; Grote, J. Tetrahedron: Asymmetry 1997, 8, 2099-2100.
13. Adamczyk, M.; Grote, J.; Rege, S. Tetrahedron: Asymmetry 1997, 8, 2509-2512.
14. Chamorro, C.; Gonzales-Muñiz, R.; Conde, S. Tetrahedron: Asymmetry 1995, 6, 2343-2352.
15. Djeghaba, Z.; Deleuze, H.; De Jeso, B.; Messadi, D.; Maillard, B. Tetrahedron Lett. 1991, 32, 761-762.
16. Gotor, V.; Brieva, R.; Rebolledo, F. J. Chem. Soc., Chem. Commun. 1988, 957-958.
17. Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1990, 1386-1387.
18. Gotor, V.; García, M. J.; Rebolledo, F. Tetrahedron: Asymmetry 1990, 1, 277-278.
19. Fernández, S.; Brieva, R.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans, 1 1992, 2885-2889.
20. Gotor, V.; Menéndez, E.; Mouloungui, Z.; Gaset, A. J. Chem. Soc., Perkin Trans, 1 1993, 2453-2456.
21. Puertas, S.; Brieva, R.; Rebolledo, F.; Gotor, V. Tetrahedron 1993, 49, 4007-4014.
22. Pozo, M.; Gotor, V. Tetrahedron 1993, 49, 4321-4326.
23. Garcia, M. J.; Rebolledo, F.; Gotor, F. Tetrahedron 1994, 50, 6935-6940.
24. Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1994, 829-832.
25. Puertas, S.; Rebolledo, F.; Gotor, F. Tetrahedron 1995, 51, 1495-1502.
26. Pozo, M.; Gotor, V. Tetrahedron: Asymmetry 1995, 6, 2797-2802.
27. Alfonso, I.; Astorga, C.; Rebolledo, F.; Gotor, V. J. Chem. Soc., Chem. Commun. 1996, 2471-2472.
28. Sánchez, V. M.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 37-40.
29. Iglesias, L. E.; Sánchez, V. M.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 2675-2677.
30. Maestro, A.; Astorga, C.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 3153-3159.
31. Gutman, A. L.; Meyer, E.; Yue, X.; Abell, C. Tetrahedron Lett. 1992, 33, 3943-3946.
32. Vörde, C.; Högberg, H.-E.; Hedenström, E. Tetrahedron: Asymmetry 1996, 7, 1507-1513.
33. Kanerva, L. T.; Csomós, P.; Sundholm, O.; Bernáth, G.; Fülöp, F. Tetrahedron: Asymmetry 1996, 7, 1705-1716.
34. Margolin, A. L.; Klibanov, A. M. J. Am. Chem. Soc. 1987, 109, 3802-3804.
35. Yang, F.; Hoenke, C.; Prinzbach, H. Tetrahedron Lett. 1995, 36, 5151-5154.
36. De Castro, M. S.; Sinisterra Gago, J. V. Tetrahedron 1998, 54, 2877-2892.
37. West, J. B.; Wong, C.-H. Tetrahedron Lett. 1987, 28, 1629-1632.
38. Gutman, A. L.; Meyer, E.; Kalerin, E.; Polyak, F.; Sterling, J. Biotech. and Bioeng. 1992, 40, 760-767.
39. Schuster, M.; Munoz, B.; Yuan, W.; Wong, C.-H. Tetrahedron Lett. 1993, 34, 1247-1250.
40. Orsat, B.; Alper, P. B.; Moree, W.; Mak, C.-P.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 712-713.
41. Bommarius, A. S.; Drauz, K.; Günther, K.; Kanup, G.; Schwarm, M. Tetrahedron: Asymmetry 1997 8, 3197-3200.
42. Easton, C. J.; Harper, J. B. Tetrahedron Lett. 1998, 39, 5269-5272.
43. Cainelli, G.; Giacomini, D.; Galletti, P.; DaCol, M. Tetrahedron: Asymmetry 1997, 8, 3231-3235.
44. Grabowski, S.; Armbruster, J.; Prinzbach, H. Tetrahedron Lett. 1997, 38, 5485-5488.
45. Waldmann, H.; Reidel, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 647-649.
46. Roos, E. C.; Mooiweer, H. H.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Boesten, W. H. J.; Kamphuis, J. J. Org. Chem. 1992, 57, 6769-6778.
47. Whitmore, B. C.; Eisenberg, R. Inorg. Chem. 1983, 22, 1-3.
48. Mori, K.; Chiba, N. Liebigs Ann. Chem. 1989, 957-962.
49. Biffin, M. E. C.; Miller, J.; Paul, D. B. In The Chemistry of the Azido Group; S. Patai, Ed.; Wiley: London, 1971; pp. 57-181.
50. Vaultier, M.; Knouzi, N.; Carrié, R. Tetrahedron Lett. 1983, 24, 763-764.
51. Guanti, G.; Banfi, L.; Riva, R. Tetrahedron: Asymmetry 1995, 6, 1345-1356, and references cited therein.
52. Tsuji, K.; Terao, Y.; Achiwa, K. Tetrahedron Lett. 1989, 30, 6189-6192.
53. Secundo, F.; Riva, S.; Carrea, G. Tetrahedron: Asymmetry 1992, 3, 267-280.
54. Koziara, A.; Osowska-Pacewicka, K.; Zawadzki, S.; Zwierzak, A. Synthesis 1985, 202-204.
55. Bartra, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron 1990, 46, 587-594.
56. Rosen, T.; Lico, I. M.; Chu, D. T. W J. Org. Chem. 1988, 53, 1580-1582.
57. Yokomatsu, T.; Minowa, T.; Murano, T.; Shibuya, S. Tetrahedron 1998, 54, 9341-9356.