Facile synthesis of 3,4-dihydroxyprolines as an application of the L-threonine aldolase-catalyzed aldol reaction

被引:0
|
作者
Fujii, M [1 ]
Miura, T [1 ]
Kajimoto, T [1 ]
Ida, Y [1 ]
机构
[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo 1428555, Japan
关键词
3,4-dihydroxyproline; L-threonine aldolase; aldol reactions; alpha-hydroxy-beta-L-amino acids; enzymes;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new facile synthesis of 3,4-dihydroxyprolines was attained by taking advantage of the L-threonine aldolase, which catalyzes the aldol condensation reaction of aldehydes with glycine affording beta-hydroxy-alpha-L-amino acids.
引用
收藏
页码:1046 / 1048
页数:3
相关论文
共 38 条
  • [1] Synthesis of thymine polyoxin C by using L-threonine aldolase-catalyzed aldol reaction
    Nishiyama, Toshihiro
    Mohile, Swapnil Surendra
    Kajimoto, Tetsuya
    Node, Manabu
    HETEROCYCLES, 2007, 71 (06) : 1397 - +
  • [2] The first enantioselective synthesis of imino-deoxydigitoxose and protected imino-digitoxose by using L-threonine aldolase-catalyzed aldol condensation
    Nishiyama, Toshihiro
    Kajimoto, Tetsuya
    Mohile, Swapnil S.
    Hayama, Noboru
    Otsuda, Teppei
    Ozeki, Minoru
    Node, Manabu
    TETRAHEDRON-ASYMMETRY, 2009, 20 (02) : 230 - 234
  • [3] Application of L-threonine aldolase-catalyzed reaction for the preparation of a peptidic mimetic of RNA: A leading compound of Vero-toxin inhibitors
    Miura, T
    Fujii, M
    Shingu, K
    Koshimizu, I
    Naganoma, J
    Kajimoto, T
    Ida, Y
    TETRAHEDRON LETTERS, 1998, 39 (40) : 7313 - 7316
  • [4] Application of L-threonine aldolase-catalyzed reaction to the preparation of protected 3R,5R-dihydroxy-L-homoproline as a mimetic of idulonic acid
    Miura, T
    Kajimoto, T
    CHIRALITY, 2001, 13 (09) : 577 - 580
  • [5] Kinetic and thermodynamic control of L-threonine aldolase catalyzed reaction and its application to the synthesis of mycestericin D.
    Shibata, K
    Shingu, K
    Vassilev, VP
    Nishide, K
    Fujita, T
    Node, M
    Kajimoto, T
    Wong, CH
    TETRAHEDRON LETTERS, 1996, 37 (16) : 2791 - 2794
  • [6] A study towards efficient L-threonine aldolase-catalyzed enantio- and diastereoselective aldol reactions of glycine with substituted benzaldehydes: biocatalyst production and process development
    Baer, Katrin
    Dueckers, Nina
    Rosenbaum, Thorsten
    Leggewie, Christian
    Simon, Sabine
    Krausser, Marina
    Osswald, Steffen
    Hummel, Werner
    Groeger, Harald
    TETRAHEDRON-ASYMMETRY, 2011, 22 (09) : 925 - 928
  • [7] An asymmetric total synthesis of a potent immunosuppressant, mycestericins D and F, through an aldol reaction using L-threonine aldolase
    Nishide, K
    Shibata, K
    Fujita, T
    Kajimoto, T
    Wong, CH
    Node, M
    HETEROCYCLES, 2000, 52 (03) : 1191 - +
  • [8] SYNTHESIS OF (3S,4S)-3,4-DIHYDROXYPROLINES FROM L-TARTARIC ACID
    ARAKAWA, Y
    YOSHIFUJI, S
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (09) : 2219 - 2224
  • [9] SYNTHESIS OF 3,4-DIHYDROXYPROLINES .2. SYNTHESIS, STEREOCHEMISTRY AND REACTIVITY OF SOME 3,4-EPOXY-D,L-PROLINE DERIVATIVES
    HUDSON, CB
    ROBERTSON, AV
    SIMPSON, WRJ
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (11) : 2479 - 2498
  • [10] Diastereoselective synthesis of l-threo-3,4-dihydroxyphenylserine by low-specific l-threonine aldolase mutants
    Hui-Jeong Gwon
    Sang-Ho Baik
    Biotechnology Letters, 2010, 32 : 143 - 149