Synthesis of enantiomerically pure (purin-6-yl)phenylalanines and their nucleosides, a novel type of purine-amino acid conjugates

Journal of Organic Chemistry

Volumn 70, Issue 20, 2005, Pages 8001-8008

  Čapek, Petr ^a   Pohl, Radek ^a   Hocek, Michal ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSIS; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CROSS-COUPLING REACTIONS; NUCLEOSIDES; PURINE BASES; STEREOSELECTIVITY;

AROMATIC COMPOUNDS;

AMINO ACID; NUCLEOSIDE; PHENYLALANINE; PURINE;

AMINO ACID SYNTHESIS; ANTIMICROBIAL ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONJUGATE; COUPLING FACTOR; ENANTIOMER; ENZYME DEGRADATION; STEREOCHEMISTRY;

AMINO ACIDS; ANTIVIRAL AGENTS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; NUCLEOSIDES; PHENYLALANINE; PURINES; STEREOISOMERISM;

EID: 25444450832     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051110x     Document Type: Article

References (44)

1. (a) Hocek, M.; Holy, A.; Votruba, I.; Dvořáková, H. J. Med. Chem. 2000, 43, 1817-1825.
2. (b) Hocek, M.; Holý, A.; Votruba, I.; Dvořá ková, H. Collect. Czech. Chem. Commun. 2001, 66, 483-499.
3. (a) Bakkestuen, A. K.; Gundersen, L.-L.; Langli, G.; Liu, F.; Nolsøe, J. M. J. Bioorg. Med. Chem. Lett. 2000, 10, 1207-1210.
4. (b) Andresen, G.; Gundersen, L.-L.; Nissen-Meyer, J.; Rise, F.; Spilsberg, B. Bioorg. Med. Chem. Lett. 2002, 12, 567-569.
5. (c) Gundersen, L.-L.; Nissen-Meyer, J.; Spilsberg, D. J. Med. Chem. 2002, 45, 1383-1386.
6. Hirao, I.; Ohtsuki, T.; Fujiwara, T.; Mitsui, T.; Yokogawa, T.; Okuni, T.; Nakayama, H.; Takio, K.; Yabuki, T.; Kigawa, T.; Kodama, K.; Yokogawa, T.; Nishikawa, K.; Yokoyama, S. Nat. Biotechnol. 2002, 20, 177-182.
7. For reviews, see: (a) Hocek, M. Eur. J. Org. Chem. 2003, 245-254.
8. (b) Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875-1916.
9. Šilhár, P.; Pohl, R.; Votruba, I.; Hocek, M. Org. Lett. 2004, 6, 3225-3228.
10. Recent reviews: (a) Da Ros, T.; Spalluto, G.; Prato, M.; Saison-Behmoaras, T.; Boutorine, A.; Cacciari, B. Curr. Med. Chem. 2005, 12, 71-88.
11. (b) Pierce, T. L.; White, A. R.; Treager, G. W.; Sexton, P. M. Mini-Rev. Med. Chem. 2005, 5, 41-55.
12. Hocek, M. Heterocycles 2004, 63, 1673-1677.
13. Čapek, P.; Pohl, R.; Hocek, M. J. Org. Chem. 2004, 69, 7985-7988.
14. Nakanuta, H.; Fujiwara, M.; Yamamoto, Y. Bull. Chem. Soc. Jpn. 2000, 73, 231-235.
15. For other related 4-(borono)phenylalanine derivatives, see: (a) Nakamura, H.; Fujiwara, M.; Yamamoto, Y. J. Org. Chem. 1998, 63, 7529-7530.
16. (b) Malan, C.; Morin, C. Synlett 1996, 167-168.
17. (c) Malan, C.; Morin, C. J. Org. Chem. 1998, 63, 8019-8020.
18. (d) Firooznia, F.; Gude, C.; Chan, K.; Marcopulos, N.; Satoh, Y. Tetrahedron Lett. 1999, 40, 213-216.
19. (e) Firooznia, F.; Gude, C.; Chan, K.; Fink, C. A.; Qiao, Y.; Satoh, Y.; Marcopoulos, N.; Savage, P.; Beil, M. E.; Bruseo, C. W.; Trapani, A. J.; Jeng, A. Y. Bioorg. Med. Chem. Lett. 2001, 11, 375-378.
20. (f) Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985-3988.
21. (g) Satoh, Y.; Gude, C.; Chan, K.; Firooznia, F. Tetrahedron Lett. 1997, 38, 7645-7648.
22. Related organostannane protected with Boc/Me was reported: (a) Morera, E.; Ortar, G. Synlett 1997, 12, 1403-1405.
23. (b) Morera, E.; Ortar, G. Bioorg. Med. Chem. Lett. 2000, 10, 1815-1818.
24. (a) Havelková, M.; Hocek, M.; Česnek, M.; Dvořák, D. Synlett 1999, 1145-1147.
25. (b) Hocek, M.; Holý, A.; Votruba, I.; Dvorǎková, H. Collect. Czech. Chem. Commun. 2000, 65, 1683-1697.
26. (c) Havelková, M.; Dvořák, D.; Hocek, M. Synthesis 2001, 1704-1710.
27. (a) Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngassa, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779-7787.
28. (b) Lakshman, M. K.; Thomson, P. F.; Nuqui, M. A.; Hilmer, J. H.; Sevova, N.; Boggess, B. Org. Lett. 2002, 4, 1479-1482.
29. (c) Gunda, P.; Russon, L. M.; Lakshman, M. K. Angew. Chem., Int. Ed. 2004, 43, 6372-6377.
30. (a) Liu, J.; Robins, M. J. Org. Lett. 2004, 6, 3421-3423.
31. (b) Liu, J.; Robins, M. J. Org. Lett. 2005, 7, 1149-1151.
32. Gundersen, L. L.; Bakkestuen, A. K.; Aasen, A. J.; Overas, H.; Rise, F. Tetrahedron 1994, 50, 9743-9756.
33. Gong, Y.; He, W. Org. Lett. 2002, 4, 3803.
34. 10d-g reaction of pinacol ester of 3 with 6-iodopurine 1a gave cross-coupling product in poor yields in preliminary experiments (for details see Supporting Information at http://pubs.acs.org). Therefore, our attention turned to more reactive free boronic acids.
35. Savarin, C.; Liebeskind, L. S. Org. Lett. 2001, 3, 2149-2152.
36. Szókán, G.; Mezö, G.; Hudec, F. J. Chromatoer. 1988, 444, 115-122.
37. 9
38. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
39. Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444.
40. Mee, S. P. H.; Lee, V.; Baldwin, J. E. Angew. Chem., Int. Ed. 2004, 43, 1132-1136.
41. Other sources of fluoride anion (KF, TBAF) were ineffective in this reaction.
42. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C. J.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905-5911.
43. Nicolaou, K. C.; Bella, M.; Chen, D. Y.-K.; Huang, X.; Ling, T.; Snyder, S. A. Angew. Chem., Int. Ed. 2002, 41, 3495-3499.
44. Stuyver, L. J.; Whitaker, T.; McBrayer, T. R.; Hernandez-Santiago, B. I.; Lostia, S.; Tharnish, P. M.; Ramesh, M.; Chu, C. K.; Jordan, R.; Shi, J. X.; Rachakonda, S.; Watanabe, K. A.; Otto, M. J.; Schinazi, R. F. Antimicrob. Agents Chemother. 2003, 47, 244-254.