An efficient chemoenzymatic route to dihydroxy acetone phosphate from glycidol for the in situ aldolase-mediated synthesis of monosaccharides

被引:22
作者
Charmantray, F
Dellis, P
Samreth, S
Hecquet, L
机构
[1] Univ Clermont Ferrand, CNRS, UMR 6504, Lab SEESIB, F-63117 Aubiere, France
[2] Synkem SAS, F-21300 Chenove, France
[3] Fournier Pharma, F-21121 Daix, France
关键词
DHAP; multienzymatic synthesis; aldolase; C-C bond formation;
D O I
10.1016/j.tetlet.2006.03.036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a new two-step procedure that uses inexpensive rac-glycidol to obtain valuable dihydroxyacetone phosphate (DHAP), a building block for the synthesis of monosaccharide analogues. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3261 / 3263
页数:3
相关论文
共 14 条
[1]   Modified L-threose and D-erythrose as substrates of transketolase and fructose-1,6-bisphosphate aldolase.: Application to the synthesis of new heptulose analogues [J].
André, C ;
Guérard, C ;
Hecquet, L ;
Demuynck, C ;
Bolte, J .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 1998, 5 (5-6) :459-466
[2]  
BERGMEYER HU, 1984, METHOD ENZYMAT AN, V2, P146
[3]  
BERGMEYER HU, 1984, METHOD ENZYMAT AN, V4, P342
[4]  
BROCKAMP HP, 1990, APPL MICROBIOL BIOT, V34, P287
[5]   Improved straightforward chemical synthesis of dihydroxyacetone phosphate through enzymatic desymmetrization of 2,2-dimethoxypropane-1,3-diol [J].
Charmantray, F ;
El Blidi, L ;
Gefflaut, T ;
Hecquet, L ;
Bolte, J ;
Lemaire, M .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (26) :9310-9312
[6]   Chemoenzymatic synthesis of chiral substituted acrylate and acrylonitrile precursors for the synthesis of 3-deoxy-2-ulosonic acids and α-methylene-γ-lactones [J].
Crestia, D ;
Guérard, C ;
Veschambre, H ;
Hecquet, L ;
Demuynck, C ;
Bolte, J .
TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :869-876
[7]   ENZYMES IN ORGANIC-SYNTHESIS .7. SYNTHESIS OF DIHYDROXYACETONE PHOSPHATE (AND ISOSTERIC ANALOGS) BY ENZYMATIC OXIDATION - SUGARS FROM GLYCEROL [J].
FESSNER, WD ;
SINERIUS, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (02) :209-212
[8]   Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics [J].
Gijsen, HJM ;
Qiao, L ;
Fitz, W ;
Wong, CH .
CHEMICAL REVIEWS, 1996, 96 (01) :443-473
[9]   Coimmobilization of L-alpha-glycerophosphate oxidase with catalase and its application for the synthesis of dihydroxyacetone phosphate [J].
Kramer, L ;
Steckhan, E .
TETRAHEDRON, 1997, 53 (43) :14645-14650
[10]   Short and efficient synthesis of a stock material of dihydroxyacetone phosphate from glycidol [J].
Meyer, O ;
Rohmer, M ;
Grosdemange-Billiard, C .
TETRAHEDRON LETTERS, 2004, 45 (42) :7921-7923