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

被引:66
作者
Shibata, K
Shingu, K
Vassilev, VP
Nishide, K
Fujita, T
Node, M
Kajimoto, T
Wong, CH
机构
[1] KYOTO PHARMACEUT UNIV, KYOTO, KYOTO 607, JAPAN
[2] INST PHYS & CHEM RES, FRONTIER RES PROGRAM, WAKO, SAITAMA 35101, JAPAN
[3] SCRIPPS RES INST, LA JOLLA, CA 92037 USA
关键词
D O I
10.1016/0040-4039(96)00430-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
L-Threonine aldolase catalyzes the aldol condensation of gamma-benzyloxybutanal and glycine with high erythrolthreo selectivity under a kinetically controlled condition. The erythro product was used in the synthesis of mycestericin D, a potent immunosupressant. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2791 / 2794
页数:4
相关论文
共 12 条
  • [1] FUJITA T, 1995, TETRAHEDRON LETT, V36, P8599
  • [2] 2-SUBSTITUTED 2-AMINOETHANOL - MINIMUM ESSENTIAL STRUCTURE FOR IMMUNOSUPPRESSIVE ACTIVITY OF ISP-I (MYRIOCIN)
    FUJITA, T
    HIROSE, R
    HAMAMICHI, N
    KITAO, Y
    SASAKI, S
    YONETA, M
    CHIBA, K
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (16) : 1857 - 1860
  • [3] FUNGAL METABOLITES .11. A POTENT IMMUNOSUPPRESSIVE ACTIVITY FOUND IN ISARIA-SINCLAIRII METABOLITE
    FUJITA, T
    INOUE, K
    YAMAMOTO, S
    IKUMOTO, T
    SASAKI, S
    TOYAMA, R
    CHIBA, K
    HOSHINO, Y
    OKUMOTO, T
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (02) : 208 - 215
  • [4] SERINE PALMITOYLTRANSFERASE IS THE PRIMARY TARGET OF A SPHINGOSINE-LIKE IMMUNOSUPPRESSANT, ISP-1/MYRIOCIN
    MIYAKE, Y
    KOZUTSUMI, Y
    NAKAMURA, S
    FUJITA, T
    KAWASAKI, T
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1995, 211 (02) : 396 - 403
  • [5] REGIOSELECTIVE RING-OPENING OF UNSYMMETRICAL CYCLIC ETHERS WITH THE ALCL3-NAI-ACETONITRILE SYSTEM - APPLICATION TO HYDROXYLATION OF ENT-KAURENE
    NODE, M
    KAJIMOTO, T
    NISHIDE, K
    FUJITA, E
    FUJI, K
    [J]. TETRAHEDRON LETTERS, 1984, 25 (02) : 219 - 222
  • [6] NODE M, 1983, CHEM PHARM BULL, V31, P4178
  • [7] Node M., 1992, BULL INST CHEM RES K, V70, P308
  • [8] ASYMMETRIC TOTAL SYNTHESIS OF ISP-I (MYRIOCIN, THERMOZYMOCIDIN), A POTENT IMMUNOSUPPRESSIVE PRINCIPLE IN THE ISARIA-SINCLAIRII METABOLITE
    SANO, S
    KOBAYASHI, Y
    KONDO, T
    TAKEBAYASHI, M
    MARUYAMA, S
    FUJITA, T
    NAGAO, Y
    [J]. TETRAHEDRON LETTERS, 1995, 36 (12) : 2097 - 2100
  • [9] FUNGAL METABOLITES .14. NOVEL POTENT IMMUNOSUPPRESSANTS, MYCESTERICINS, PRODUCED BY MYCELIA-STERILIA
    SASAKI, S
    HASHIMOTO, R
    KIUCHI, M
    INOUE, K
    IKUMOTO, T
    HIROSE, R
    CHIBA, K
    HOSHINO, Y
    OKUMOTO, T
    FUJITA, T
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (04) : 420 - 433
  • [10] AMINO-ACIDS AND PEPTIDES .62. SYNTHESIS OF (4R)-4-((E)-2-BUTENYL)-4,N-DIMETHYL-L-THREONINE (MEBMT), THE CHARACTERISTIC AMINO-ACID OF CYCLOSPORINE
    SCHMIDT, U
    SIEGEL, W
    [J]. TETRAHEDRON LETTERS, 1987, 28 (25) : 2849 - 2852