One-pot conversion of serine and α-methylserine derivatives to the corresponding cysteines and selenocystines by using chalcogenophosphate reagents

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 186, Issue 1, 2010, Pages 125-133

  Makiyama, Akira ^a   Komatsu, Itsuki ^a   Iwaoka, Michio ^a   Yatagai, Masanobu ^b  

^a TOKAI UNIVERSITY   (Japan)

^b AJINOMOTO CO INC   (Japan)

Author keywords

Alcohols; amino acids; selenium; sulfur; thiols

Indexed keywords

EID: 78751553169     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426507.2010.485155     Document Type: Article

References (53)

1. Pedersen, B. S.; Scheibye, S.; Nilsson, N. H.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1978, 87, 223.
2. (a)Wood, P. T.; Woollins, J. D. J. Chem. Soc., Chem. Commun. 1988, 1190;
3. (b) Gray, I. P.;Bhattacharyya, P.; Slawin, A. M. Z.; Woollins, J. D. Chem. Eur. J. 2005, 11, 6221;
4. (c) Hua, G.;Woollins, J. D. Angew. Chem. Int. Ed. 2009, 48, 1368.
5. Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2007, 107, 5210, and the cited therein.
6. (a) Bhattacharyya, P.; Woollins, J. D.; Tetrahedron Lett. 2001, 42, 5949;
7. (b)Baxter, I.; Hill, A. F.; Malget, J. M.; White, A. J. P.; Williams, D. J. Chem. Commun. 1997, 2049.
8. (a) Nishio, T. J. Chem. Soc., Chem. Commun. 1989, 205;
9. (b) Nishio, T. J. Chem. Soc., Perkin Trans. 1 1993, 1113;
10. (c) Nishio, T. Tetrahedron Lett. 1995, 36, 6113;
11. (d) Nishio, T. J. Org. Chem. 1997, 62, 1106.
12. (a) Bartsch, H.; Erker, T. Tetrahedron Lett. 1992, 33, 199;
13. (b)Tewari, N.; Kumar, Y.; Thaper, R. K.; Khanna, J. M. Synth. Commun. 1996, 26, 1169;
14. (c) Bates, D. K.; Li, X.; Jog, P. V. J. Org. Chem. 2004, 69, 2750.
15. Mohanakrishnan, A. K.; Amaladass, P. Tetrahedron Lett. 2005, 46, 7201.
16. Bhatia, S. K.; Hajdu, J. Tetrahedron Lett. 1988, 29, 31.
17. (a) Kedrowski, B. L.; Heathcock, C. H. Heterocycles 2002, 58, 601;
18. (b) Nagasawa, T.; Hosono, H.; Yamano, H.; Ohkishi, H.; Tani, Y.; Yamada, H. Agric. Biol. Chem. 1983, 47, 861.
19. Arnold, L. D.; May, R. G.; Vederas, J. C. J. Am. Chem. Soc. 1988, 110, 2237.
20. Nelson, D. L.; Cox, M. M. Lehninger Principles of Biochemistry, 4th ed.; W. H. Freeman and Company: New York, 2005; Chap. 22.
21. Böck, A.; Forchhammer, K.; Heider, J.; Leinfelder, W.; Sawers, G.; Veprek, B.; Zinoni, F. Mol. Microbiol. 1991, 5, 515.
22. (a) Yuan, J.; Palioura, S.; Salazar, J. C.; Su, D.; O'Donoghue, P.; Hohn, M. J.; Cardoso, A. M.; Whitman, W. B.; Söll, D. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 18923;
23. (b) Itoh, Y.; Sekine, S.; Matsumoto, E.; Akasaka, R.; Takemoto, C.; Shirouzu, M.; Yokoyama, S. J. Mol. Biol. 2009, 385, 1456.
24. Iwaoka, M.; Ooka, R.; Nakazato, T.; Yoshida, S.; Oishi, S. Chem. Biodivers. 2008, 5, 359.
25. (a) Barton, D. H. R.; Bridon, D.; Herve, Y.; Potier, P.; Thierry, J.; Zard, S. Z. Tetrahedron 1986, 42, 4983;
26. (b) Reich, H. J.; Jasperse, C. P.; Renga, J. M. J. Org. Chem. 1986, 51, 2981;
27. (c)Iwaoka, M.; Haraki, C.; Ooka, R.; Miyamoto, M.; Sugiyama, A.; Kohara, Y.; Isozumi, N. Tetrahedron Lett. 2006, 47, 3861.
28. (a) Avdillo, C.; Jiḿenez-Ośes, G.; Busto, J. H.; Peregrina, J. M.; Zurbano, M. M.; Avenoza, A. Chem. Eur. J. 2007, 13, 4840;
29. (b) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2007, 18, 569;
30. (c) Ohfune, Y.; Shinada, T. Eur. J. Org. Chem. 2005, 24, 5127.
31. (a)Nozaki, H.; Kuroda, S.; Watanabe, K.; Yokozeki, K. J. Mol. Cat. B: Enzym. 2009, 59, 237;
32. (b) Nozaki, H.; Kuroda, S.; Watanabe, K.; Yokozeki, K. J. Mol. Cat. B: Enzym. 2009, 56, 221;
33. (c) Nozaki, H.; Kuroda, S.; Watanabe, K.; Yokozeki, K. Appl. Environ. Microbiol. 2008, 74, 7596;
34. (d) Nozaki, H.; Kuroda, S.; Watanabe, K.; Yokozeki, K. Biosci. Biotech. Biochem. 2008, 72, 3002;
35. (e) Nozaki, H.; Kuroda, S.; Watanabe, K.; Yokozeki, K. Biosci. Biotech. Biochem. 2008, 72, 2580;
36. (f) Yatagai, M.; Hamada, T.; Nozaki, H.; Kuroda, S.; Yokozeki, K.; Izawa, K. In Asymmetric Synthesis and Application of á-Amino Acids; ACS Symposium Series 1009; American Chemical Society: Washington, DC, 2009; Chap. 24, pp. 394.
37. Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolomelli, A. Tetrahedron 2001, 57, 2807.
38. Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Sucunza, D.; Zurbano, M. M. Tetrahedron: Asymmetry 2001, 12, 949.
39. Myers, M. C.; Wang, J. L.; Iera, J. A.; Bang, J.; Hara, T.; Saito, S.; Zambetti, G. P.; Appella, D. H. J. Am. Chem. Soc. 2005, 127, 6152.
40. Similar reactions were reported by Kiso's group: Sohma, Y.; Sasaki, M.; Hayashi, Y.; Kimura, T.; Kiso, Y. Chem. Commun. 2004, 124.
41. Mishra, B.; Kumbhare, B. L.; Jain, K. V.; Priyadarsini, I. K. J. Phys. Chem. B 2008, 112, 4441.
42. Lafontaine, J. A.; Provencal, D. P.; Gardelli, C.; Leahy, J. W. J. Org. Chem. 2003, 68, 4215.
43. Braga, A. L.; Vargas, F.; Sehnem, J. A.; Braga, R. C. J. Org. Chem. 2005, 70, 9021.
44. Shabana, R.; Osman, F. H.; Atrees, S. S. Tetrahedron 1993, 49, 1271.
45. (a) Similar cyclization was reported previously: (a)Nishio, T.; Konno, Y.; Ori,M.; Sakamoto, M. Eur. J. Org. Chem. 2001, 3553;
46. (b) Kodama, Y.; Ori, M.; Nishio, T. Helv. Chim. Acta 2005, 88, 187.
47. Ori, M.; Nishio, T. Heterocycles 2000, 52, 111.
48. In humans, intervention of a dehydroalanine intermediate is proposed in the transformation from Ser to Sec on the Sec-tRNA: Palioura, S.; Sherrer, R. L.; Steitz, T. A.; Söll, D.; Simonovíc, M. Science 2009, 325, 321.
49. Wu, P. Z.; Hilvert, D. J. Am. Chem. Soc. 1989, 111, 4513.
50. (a) Pattenden, G.; Thom, S. M.; Jones, M. F. Tetrahedron 1993, 49, 2131;
51. (b) Bergeron, R. J.; Wiegand, J.; McManis, J. S.; Bharti, N. J. Med. Chem. 2006, 49, 7032.
52. Lin, Y. A.; Chalker, J. M.; Floyd, N.; Bernardes, G. J.; Davis, B. G. J. Am. Chem. Soc. 2008, 130, 9642.
53. Easton, C. J.; Ivory, A. J.; Smith, C. A. J. Chem. Soc., Perkin Trans. 2 1997, 503.