New continuous production process for enantiopure (2R,5R)-hexanediol

被引:45
作者
Haberland, J
Hummel, W
Daussmann, T
Liese, A [1 ]
机构
[1] Res Ctr Juelich GmbH, Inst Biotechnol, D-52425 Julich, Germany
[2] Univ Dusseldorf, Inst Enzyme Technol, D-52426 Julich, Germany
[3] Juelich Fine Chem GmbH JFC, D-52428 Julich, Germany
关键词
D O I
10.1021/op020023t
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new continuous production process has been developed for optically active pure (2R,5R)-hexanediol. The process uses resting whole cells of Lactobacillus kefir DSM 20587 as a biocatalyst. The reduction of (2,5)-hexanedione to (2R,5R)hexanediol was carried out in a 2-L continuously operated membrane reactor. Conversion of (2,5)-hexanedione was nearly quantitative and the selectivity between product and intermediate was 78% for the product. Enantioselectivity and diastereoselectivity were >99% for the whole period. The productivity of L. kefir could be increased by factor 30. (2R,5R)-Hexanediol was continuously produced over 5 days with a space-time yield of 64 g.L-1.d(-1).
引用
收藏
页码:458 / 462
页数:5
相关论文
共 13 条
[1]   Oxazaborolidine-catalysed reduction of alk-2-ene-1,4diones.: A convenient access to chiral 1,4-diols [J].
Bach, J ;
Berenguer, R ;
Garcia, J ;
López, M ;
Manzanal, J ;
Vilarrasa, J .
TETRAHEDRON, 1998, 54 (49) :14947-14962
[2]   Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols [J].
Bach, J ;
Berenguer, R ;
Garcia, J ;
Loscertales, T ;
Manzanal, J ;
Vilarrasa, J .
TETRAHEDRON LETTERS, 1997, 38 (06) :1091-1094
[3]   NEW CHIRAL PHOSPHOLANES - SYNTHESIS, CHARACTERIZATION, AND USE IN ASYMMETRIC HYDROGENATION REACTIONS [J].
BURK, MJ ;
FEASTER, JE ;
HARLOW, RL .
TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :569-592
[4]   C2-SYMMETRICAL BIS(PHOSPHOLANES) AND THEIR USE IN HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].
BURK, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8518-8519
[5]   NEW ELECTRON-RICH CHIRAL PHOSPHINES FOR ASYMMETRIC CATALYSIS [J].
BURK, MJ ;
FEASTER, JE ;
HARLOW, RL .
ORGANOMETALLICS, 1990, 9 (10) :2653-2655
[6]  
Fan QH, 1997, TETRAHEDRON-ASYMMETR, V8, P4041
[7]   Diastereoselective synthesis of optically active (2R,5R)-hexanediol [J].
Haberland, J ;
Kriegesmann, A ;
Wolfram, E ;
Hummel, W ;
Liese, A .
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 2002, 58 (05) :595-599
[8]  
HUMMEL W, 2000, Patent No. 00113127512110
[9]   Yeast-mediated synthesis of optically active diols with C-2-symmetry and (R)-4-pentanolide [J].
Ikeda, H ;
Sato, E ;
Sugai, T ;
Ohta, H .
TETRAHEDRON, 1996, 52 (24) :8113-8122
[10]  
LIESE A, 2000, IND BIOTRANSFORMATIO, P93