Enantioselective synthesis of d- and l-α-methylcysteine with hydantoinase

Tetrahedron Letters

Volumn 48, Issue 19, 2007, Pages 3437-3440

  Ohishi, Takahiro ^a   Nanba, Hirokazu ^a   Sugawara, Masanobu ^a   Izumida, Masashi ^a   Honda, Tatsuya ^a   Mori, Kohei ^a   Yanagisawa, Satohiro ^a   Ueda, Makoto ^a   Nagashima, Nobuo ^a   Inoue, Kenji ^a  

^a KANEKA CORPORATION   (Japan)

Author keywords

Methylcysteine; Enantioselective synthesis; Hydantoinase; Scalable process; tert Butyl group

Indexed keywords

DIHYDROPYRIMIDINASE; MECYSTEINE;

ARTICLE; CYCLIZATION; ENANTIOSELECTIVITY; FILTRATION; HYDROLYSIS; SYNTHESIS;

EID: 34247125957     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.040     Document Type: Article

References (33)

1. Carmeli S., Moore R.E., and Patterson G.M.L. Tetrahedron Lett. 32 (1991) 2593
2. Akaji K., Kuriyama N., and Kiso Y. J. Org. Chem. 61 (1996) 3350
3. Walker M.A., and Heathcock C.H. J. Org. Chem. 57 (1992) 5566
4. Parsons R.L., and Heathcock C.H. Tetrahedron Lett. 35 (1994) 1383
5. Parsons R.L., and Heathcock C.H. Tetrahedron Lett. 35 (1994) 1379
6. Carmeli S., Paik S., Moore R.E., Patterson G.M.L., and Yoshida W.Y. Tetrahedron Lett. 34 (1993) 6681
7. Carmeli S., Moore R.E., Patterson G.M.L., Corbett T.H., and Valoriote F.A. J. Am. Chem. Soc. 112 (1990) 8195
8. Jansen R., Kunze B., Reichenbach H., Jurkiewicz E., Hunsmann G., and Höfle G. Liebigs Ann. Chem. (1992) 357
9. Jansen R., Schomburg D., and Höfle G. Liebigs Ann. Chem. (1993) 701
10. Jurkiewicz E., Jansen R., Kunze B., Trowitzsch-Kienast W., Forche E., Reichenbach H., Holfe G., and Hunsmann G. Antiviral Chem. Chemother. 3 (1992) 189
11. Groth U., and Schöllkopf U. Synthesis 1 (1983) 37
12. Singh S., Rao S.J., and Pennington M.W. J. Org. Chem. 69 (2004) 4551
13. Pattenden G., Thom S.M., and Jones M.F. Tetrahedron 49 (1993) 2131
14. Mulqueen G.C., Pattenden G., and Whiting D.A. Tetrahedron 49 (1993) 5359
15. Shao H., Zhu Q., and Goodman M. J. Org. Chem. 60 (1995) 790
16. Fukuyama T., and Xu L. J. Am. Chem. Soc. 115 (1993) 8449
17. Smith N.D., and Goodman M. Org. Lett. 5 (2003) 1035
18. Kedrowski B.L. J. Org. Chem. 68 (2003) 5403
19. Inoue A., Komeda H., and Asano Y. Adv. Synth. Catal. 347 (2005) 1132
20. Yamada H., Takahashi S., Kii Y., and Kumagai H. J. Ferment. Technol. 56 (1978) 484
21. Takahashi S., Kii Y., Kumagai H., and Yamada H. J. Ferment. Technol. 56 (1978) 492
22. Takahashi S., Ohashi T., Kii Y., Kumagai H., and Yamada H. J. Ferment. Technol. 57 (1979) 328
23. Oh C.-H., Kang Y.-K., Park S.-W., and Cho J.-H. Bull. Korean Chem. Soc. 9 (1988) 231
24. Takahashi, S.; Yamada, Y.; Ueda, Y.; Katayama, Y.; Shimada, Y.; Watanabe, K. Patent JP61,072,762.
25. Nanba, H.; Yajima, K.; Takano, M.; Yamada, Y.; Ikenaka, Y.; Takahashi, S. Patent WO96/20275.
26. Multigram syntheses of (l)-3 and (d)-2. Compound 3 (267 g, 1.14 mol) was added to a 3.2% aq NaCl solution (1405 g), and the resultant mixture was adjusted to pH 6.5 with aq NaOH solution. Then, immobilized hydantoinase (total 87 g, wet weight) and manganese sulfate pentahydrate (0.44 g) were added to the mixture, and the reaction was performed by stirring at 40 °C for 41.5 h. During the reaction, the pH was kept at 6.5 using 10% aqueous sulfuric acid solution. After the reaction, a mixture of the precipitate and the immobilized hydantoinase was filtered off and washed with water (300 g). (d)-2 was obtained in the mixture (132.6 g, yield 43.9%, optical purity 97.8% ee). The filtrate was washed with ethyl acetate (300 g) twice, and cooled to 20 °C. Then the filtrate was adjusted to pH 3 with concd HCl (59 g) and stirred for 30 min. The precipitated solid was filtered off, washed with water, and (l)-3 was obtained as white crystals. (132.6 g, yield 49.6%) The chemical purity was 97.3 area% by HPLC (column, COSMOSIL 5C8-MS (produced by Nacalai Tesque Inc), mobile phase, potassium dihydrogen phosphate-phosphoric acid solution (pH 2.0)/acetonitrile = 80/20, flow rate, 1.0 ml/min, detection wavelength, 210 nm, column temperature, 40 °C). The optical purity was 99.5% ee by HPLC (column, CHIRALPAK AS (produced by Daicel Chemical Industries, Ltd), mobile phase, hexane/2-propanol/trifluoroacetic acid = 80/20/0.1, flow rate, 0.5 ml/min, detection wavelength, 210 nm, column temperature, 30 °C). The yield and optical purity of (d)-2 were determined by HPLC (For yield: column, COSMOSIL 5C18-AR (produced by Nacalai Tesque Inc), mobile phase, potassium dihydrogen phosphate-phosphoric acid solution (pH 2.0)/acetonitrile = 70/30, flow rate, 1.0 ml/min, detection wavelength, 210 nm, column temperature, 40 °C), For optical purity: column, CHIRALPAK AS (produced by Daicel Chemical Industries, Ltd), mobile phase, hexane/2-propanol/trifluoroacetic acid = 85/15/0.1, flow rate, 1.0 ml/min, detection wavelength, 210 nm, column temperature, 30 °C.
27. Yajima H., Fujii N., Funakoshi S., Watanabe T., Murayama E., and Otaka A. Tetrahedron 44 (1988) 805
28. Fujii N., Otaka A., Ikemura O., Hatano M., Okamachi A., Funakoshi S., Sakurai M., Shioiri T., and Yajima H. Chem. Pharm. Bull. 35 (1987) 3447
29. Fujii N., Otaka A., Sugiyama N., Hatano M., and Yajima H. Chem. Pharm. Bull. 35 (1987) 3880
30. Fujii N., Otaka A., Funakoshi S., Bessho K., and Yajima H. J. Chem. Soc., Chem. Commun. 3 (1987) 163
31. Akaji K., Yoshida M., Tatsumi T., Kimura T., Fujiwara Y., and Kiso Y. J. Chem. Soc., Chem. Commun. 4 (1990) 288
32. Almstead et al. reported that tert-butyl group of thio-bisphosphonate was cleaved simply by heating with concd HCl. Almstead N.G., Dansereau S.M., Francis M.D., Snider C.M., Ebetino F.H. Phosphorus, Sulfur and Silicon 144-146 (1999) 325
33. 1H NMR analysis of the residue, it was confirmed that the desired compound (106 mg, yield 60%) had been produced. The HPLC analysis (column, CHIRALCEL OD-RH (produced by Daicel Chemical Industries, Ltd), mobile phase, potassium dihydrogen phosphate-phosphoric acid solution (pH 2.0)/acetonitrile = 6/4, flow rate, 1.0 ml/min, detection wavelength, 210 nm, column temperature, 30 °C, retention time, 19.15 min (d), 22.92 min (l)) of the compound showed an optical purity of 99.6% ee.