Kinetic and thermodynamic control of L-threonine aldolase catalyzed reaction and its application to the synthesis of mycestericin D

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2791-2794

  Shibata, Kayoko ^a   Shingu, Kazushi ^b   Vassilev, Vassil P ^b   Nishide, Kiyoharu ^a   Fujita, Tetsuro ^a   Node, Manabu ^a   Kajimoto, Tetsuya ^b   Wong, Chi Huey ^b,c  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FRUCTOSE BISPHOSPHATE ALDOLASE; IMMUNOSUPPRESSIVE AGENT; MYCESTERICIN D; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; ENZYME ACTIVITY; STEREOCHEMISTRY; TECHNIQUE; THERMODYNAMICS;

EID: 0029942468     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00430-3     Document Type: Article

References (15)

1. Vassilev, V. P.; Uchiyama, T; Kajimoto, T; Wong, C.-H. Tetrahedron Lett. 1995, 36, 4081.
2. Idem, ibid. 1995, 36, 5063.
3. a) Miyake, Y.; Kozutsumi, Y.; Nakamura, S.; Fujita, T.; Kawasaki, T. Biochem. & Biophys. Res. Comm. 1995, 211, 396.
4. b) Fujita, T.; Hirose, R.; Hamamichi, N.; Kitao, Y.; Sasaki, S; Yoneta, M.; Chiba, K. Bioorg. & Med. Chem. Lett. 1995, 5, 1857.
5. c) Fujita, T.; Inoue, K.; Yamamoto, S.; Ikumoto, T.; Sasaki, S.; Toyama, R.; Chiba, K.; Hoshino, Y.; Okumoto, T. J. Antibiotics 1994, 47, 208.
6. d) Sasaki, S.; Hashimoto, R.; Kiuchi, M.; Inoue, K.; Ikumoto, T.; Hirose, R.; Chiba, K.; Hoshino, Y.; Okumoto T.; Fujita, T. Ibid. 1994, 47, 420.
7. e) Sano, S.; Kobayashi, Y.; Kondo, T.; Takebayashi, M.; Maruyama, S.; Fujita T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097.
8. f) Fujita, T.; Hamamichi, N.; Matsuzaki, T.; Kitao, Y.; Kiuchi, M.; Node M.; Hirose, R. Tetrahedron Lett. 1995, 36, 8599.
9. Schmidt, U.; Siegel, W. Tetrahedron Lett. 1987, 28, 2849.
10. The value of e.e. was determined by chiral HPLC [DAICEL CHIRALCEL OD (hexane:i-PrOH = 9 : 1)]
11. 3) δ 7.80 - 7.97(2H, m), 7.54 -7.26(8H, m), 4.57(1H, dd, J = 8.8, 4.6), 4.54(1H, d, A part of AB, J = 11.3), 4.51(2H, s), 4.39 (1H, d, B part of AB, J = 11.3), 3.77(3H, s), 3.56 - 3.49(2H. m), 2.03(3H, s), 1.94 - 1.71(4H, m).
12. a) Node, M.; Kajimoto, T.; Nishide, K.; Fujita, E.; Fuji, K. Bull. Inst. Chem. Res., Kyoto Univ. 1992, 70, 308.
13. b) Node, M.; Ohta, K.; Kajimoto, T.; Nishide, K.; Fujita, E.; Fuji, K. Chem. Pharm. Bull. 1983, 31, 4178.
14. Node, M.; Kajimoto, T.; Nishide, K.; Fujita, E.; Fuji, K. Tetrahedron Lett. 1984, 25, 219.
15. 3) δ 8.02 - 7.99(2H, m), 7.55 -7.40(3H. m), 5.50(1H, dt, J = 15.4, 6.4), 5.38(1H, dt, J = 15.4, 6.5), 4.55(1H, dd, J = 10.0, 3.6), 4.54, 4.39(each 1H, d, AB type, J = 11.2), 3.92(4H, s), 3.78(3H, s), 2.30 - 2.16(2H, m), 2.05(3H, s), 1.99(2H, br q, J = 6.7), 1.73 - 1.56(6H, m), 1.29 - 1.24(16H, m), 0.88(3H, t, J = 6.7).