Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution

Tetrahedron Asymmetry

Volumn 23, Issue 13, 2012, Pages 938-944

  D'Arrigo, Paola ^a   Cerioli, Lorenzo ^a   Fiorati, Andrea ^a   Servi, Stefano ^a   Viani, Fiorenza ^b   Tessaro, Davide ^a  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 ALPHA NAPHTHYLALANINE; 1 ALPHA NAPHTHYLGLYCINE; 2 ALPHA NAPHTHYLALANINE; 2 ALPHA NAPHTHYLGLYCINE; ALANINE DERIVATIVE; GLYCINE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RACEMIZATION;

EID: 84864682996     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.06.020     Document Type: Article

References (71)

1. D.E. Cane, C.T. Walsh, and C. Khosla Science 282 1998 63 68
2. M. Strieker, and M.A. Marahiel ChemBioChem 10 2009 607 616
3. S. Caboche, M. Pupin, V. Leclere, P. Jacques, and G. Kucherov BMC Struct. Biol. 9 2009 15 10.1186/1472-6807-9-15
4. A.M. Rouhi Chem. Eng. News 82 2004 47 62
5. A. Schmid, J.S. Dordick, B. Hauer, A. Kiener, M. Wubbolt, and B. Witholt Nature 409 2001 258 268
6. H.E. Schoemake, D. Mink, and M.G. Wubbolts Science 299 2003 1694 1697
7. A.J. Loffet Pep. Sci. 8 2002 1 7
8. S. Kee, and S.D.S. Jois Curr. Pharm. Design 9 2003 1209 1224
9. S. Hanessian, G. McNaughton Smith, and H.G. Lombart Tetrahedron 53 1997 12789 12854
10. L. Wang, and P.G. Schultz Angew. Chem., Int. Ed. 44 2005 34 66
11. H. Sun, Z. Nikolovska-Coleska, C.Y. Yang, L. Xu, M. Liu, Y. Tomita, H. Pan, Y. Yoshioka, K. Krajewski, P.P. Roller, and S. Wang J. Am. Chem. Soc. 126 2004 16686 16687
12. T.K. Oost, C. Sun, R.C. Armstrong, A.S. Al-Assaad, S.F. Betz, T.L. Deckwerth, H. Ding, S.W. Elmore, R.P. Meadows, E.T. Olejniczak, A. Oleksijew, T. Oltersdorf, S.H. Rosenberg, A.R. Shoemaker, K.J. Tomaselli, H. Zou, and S.W. Fesik J. Med. Chem. 47 2004 4417 4426
13. R.M. Williams Synthesis of Optically Active α-Amino Acids 1989 Pergamon Oxford
14. T. Wirth Angew. Chem., Int. Ed. 36 1997 225 227
15. J.A. Ma Angew. Chem., Int. Ed. 42 2003 4290 4299
16. M.J. Burk Acc. Chem. Res. 33 2000 363 372
17. R. Noyori, and T. Ohkuma Angew. Chem., Int. Ed. 40 2001 40
18. H.K. Chenault, J. Dahmer, and G.M. Whitesides J. Am. Chem. Soc. 111 1989 6354 6364
19. T. Miyazawa, H. Minowa, T.K. Miyamoto, R. Imagawa, T. Yanagihara, and Y. Yamada Tetrahedron: Asymmetry 8 1997 367 370
20. S.-T. Chen, W.-H. Huang, and K.T. Wang J. Org. Chem. 59 1994 7580 7581
21. S.T. Chen, W.H. Huang, and K.T. Wang Chirality 6 1994 572 576
22. M. Pugniere, N. Domergue, B. Castro, and A. Previero Chirality 6 1994 472 478
23. N.A. Sasaki, C. Hachimoto, and P. Potier Tetrahedron Lett. 48 1987 6069 6072
24. T. Miyazawa Amino Acids 16 1999 191 213
25. E. Agosta, A. Caligiuri, P. D'Arrigo, S. Servi, D. Tessaro, and R. Canevotti Tetrahedron: Asymmetry 17 2006 1995 1999
26. L.P.B. Gonalves, O.A.C. Antunes, G.F. Pinto, and E.G. Oestreicher Tetrahedron: Asymmetry 11 2000 1465 1468
27. T. Li, A.B. Kootstra, and I.G. Fotheringham Org. Proc. Res. Dev. 6 2002 533 538
28. J.D. Stewart Curr. Opin. Chem. Biol. 5 2001 120 129
29. P.P. Taylor, D.P. Pantaleone, R.F. Senkpeil, and I.G. Fotheringham Trends Biotechnol. 16 1998 412 418
30. N. Hovhannisyan, S. Harutyunyan, A. Hovhannisyan, A. Hambardzumyan, M. Chitchyan, M. Melkumyan, G. Oganezova, and N. Avetisyan Amino Acids 37 2009 531 536
31. P. Chrisp, and K.L. Goa Drugs 39 1990 523 551
32. R. Hirayama, M. Yamamoto, T. Tsukida, K. Matsuo, Y. Obata, F. Sakamoto, and S. Ikeda Bioorg. Med. Chem. 5 1997 765 777
33. Cooper, R.D.G.; Blaszczak, L.C.; Turner, J.R.; Conrad, P.C.; Daugherty, B.W.; Wade, B. US 83-484128 19830412 CAN 102:148986.
34. J.E. Rivier, J. Porter, C.L. Rivier, M. Perrin, A. Corrigan, W.A. Hook, R.P. Siraganian, and W.W. Vale J. Med. Chem. 29 1986 1846 1851
35. Y. Yabe, A. Morita, C. Miura, S. Kobayashi, and Y. Baba Chem. Pharm. Bull. 25 1977 2731 2734
36. Z. Prochazka, and J. Slaninova Collect. Czech. Chem. Commun. 60 1995 2170 2177
37. T. Hohsaka, D. Kajihara, Y. Ashizuka, H. Murakami, and M. Sisido J. Am. Chem. Soc. 121 1999 34 40
38. T.A. Tran, R.H. Mattern, B.A. Morgan, J.E. Taylor, and M. Goodman J. Pept. Sci. 5 1999 113 130
39. B.E. Haug, M.L. Skar, and J.S. Svendsen J. Pept. Sci. 7 2001 425 432
40. L. Ranjalahy-Rasoloarijao, R. Lazaro, P. Daumas, and F. Heitz Int. J. Pep. Prot. Res. 33 1989 273 280
41. M. Sobocinska, E. Lempicka, E. Konieczna, L. Derdowska, B. Lammek, S. Melhem, W. Kozik, J. Janecka, M. Janecki, and H.I. Trzeciak J. Pharm. Pharmacol. 52 2000 1105 1112
42. H. Tamamura, A. Omagari, K. Hiramatsu, S. Oishi, H. Habashita, T. Kanamoto, K. Gotoh, N. Yamamoto, H. Nakashima, A. Otaka, and N. Fujii Bioorg. Med. Chem. 10 2002 1417 1426
43. P. Daumas, and F. Heitz Biochemie 71 1989 77 81
44. H.L. Lingen, J.K.W. Van de Mortel, K.F.W. Hekking, F.L. Van Delft, T. Sonke, and F.P.J.T. Rutjes J. Eur. Org. Chem. 2003 317 324
45. X. Zhang, J. Ouyang, W.R.G. Baeyens, S. Zhai, Y. Yang, and G. Huang J. Pharm. Biomed. Anal. 31 2003 1047 1057
46. X. Zhang, J. Ouyang, and Y. Yang Anal. Lett. 34 2001 1851 1864
47. R.M. Williams, and J.A. Hendrix J. Org. Chem. 55 1990 3723 3728
48. E. Reimann, and D. Voss Arch. Pharmazie 309 1976 978 983
49. H.R. Dave, and B.D. Hosangadi Tetrahedron 55 1999 11295 11308
50. M. Pugniere, B. Castro, and A. Previero Chirality 3 1991 170 173
51. C. Syldtak, D. Voelkel, U. Bilitewski, K. Krohn, H. Hoeke, and F. Wagner Biotechnol. Lett. 14 1992 105 110
52. A. Caligiuri, P. D'Arrigo, T. Gefflaut, G. Molla, L. Pollegioni, E. Rosini, C. Rossi, and S. Servi Biocat. Biotrans. 24 2006 409 413
53. R.A. Sheldon Chem. Ind. (London) 1992 903
54. S. Hanzawa, S. Oe, K. Tokuhisa, K. Kawano, T. Kobayashi, T. Kudo, and H. Kakidani Biotechnol. Lett. 23 2001 589 591
55. A. Caligiuri, P. D'Arrigo, E. Rosini, G. Molla, S. Servi, D. Tessaro, and L. Pollegioni Adv. Synth. Catal. 348 2006 2183 2190
56. D'Arrigo, P.; Cerioli, L.; Servi, S.; Tessaro, D.; Viani, F. submitted for publication.
57. S. Iriuchijima, and N. Kojima J. Chem. Soc., Chem. Commun 1981 185
58. A. Zaks, and A.M. Klibanov Proc. Natl. Acad. Sci. U.S.A. 82 1985 3192 3196
59. D. Bianchi, and P. Cesti J. Org. Chem. 55 1990 5657 5659
60. H. Frykman, N. Ohrner, T. Norin, and K. Hult Tetrahedron Lett. 8 1993 1367 1370
61. M. Caussette, A. Marty, and D.J. Combes Chem. Tech. Biotechnol. 68 1997 257 262
62. K.C. Sproull, G.T. Bowman, G. Carta, and J.L. Gainer Biotechnol. Progress 13 1997 71 76
63. G.E. Lienhard, and T.C. Wang J. Am. Chem. Soc. 90 1968 3781 3787
64. P.J. Um, and D.G. Drueckhammer J. Am. Chem. Soc. 120 1998 5605 5610
65. D. Arosio, G. Pedrocchi-Fantoni, C. Rossi, C. Saraceno, S. Servi, and D. Tessaro Adv. Synth. Catal. 349 2007 1345 1348
66. P. D'Arrigo, D. Arosio, L. Cerioli, D. Moscatelli, S. Servi, F. Viani, and D. Tessaro Tetrahedron: Asymmetry 22 2011 851 856
67. G. Fülling, and C.J. Sih J. Am. Chem. Soc. 109 1987 2845 2846
68. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294
69. S. Atsuumi, K. Nakano, Y. Masato, S. Tanaka, and K. Matsuyama Chem. Pharm. Bull. 40 2 1992 364 370
70. M. Rodriguez, N. Bernad, M.C. Galas, M.F. Lignon, and J. Laur Eur. J. Med. Chem. 26 3 1991 245 253
71. E. Medina, A. Vidal-Ferran, A. Moyano, M.A. Pericas, and A. Riera Tetrahedron: Asymmetry 8 1997 15581 15586