SUBSTRATE-SPECIFICITY AND CARBOHYDRATE SYNTHESIS USING TRANSKETOLASE

被引:127
作者
KOBORI, Y [1 ]
MYLES, DC [1 ]
WHITESIDES, GM [1 ]
机构
[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138
关键词
D O I
10.1021/jo00048a023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.
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收藏
页码:5899 / 5907
页数:9
相关论文
共 34 条
[1]   RABBIT MUSCLE ALDOLASE AS A CATALYST IN ORGANIC-SYNTHESIS [J].
BEDNARSKI, MD ;
SIMON, ES ;
BISCHOFBERGER, N ;
FESSNER, WD ;
KIM, MJ ;
LEES, W ;
SAITO, T ;
WALDMANN, H ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :627-635
[2]   CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .1. TRANSFORMATIONS IN THE GLUCOSE SERIES [J].
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1979, 62 (06) :1990-2016
[3]   UTILIZATION OF ENZYMES IN ORGANIC-CHEMISTRY - TRANSKETOLASE CATALYZED SYNTHESIS OF KETOSES [J].
BOLTE, J ;
DEMUYNCK, C ;
SAMAKI, H .
TETRAHEDRON LETTERS, 1987, 28 (45) :5525-5528
[4]  
BOLTE J, 1987, TETRAHEDRON LETT, V28, P5523
[5]   SYNTHESIS OF ALDOSE SUGARS FROM HALF-PROTECTED DIALDEHYDES USING RABBIT MUSCLE ALDOLASE [J].
BORYSENKO, CW ;
SPALTENSTEIN, A ;
STRAUB, JA ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9275-9276
[6]  
CHAKRAVORTY M, 1962, J BIOL CHEM, V237, P1014
[7]  
Collins P. M., 1987, CARBOHYDRATES
[8]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[9]  
DATTA AG, 1961, J BIOL CHEM, V236, P617
[10]  
DATTA AG, 1961, J BIOL CHEM, V236, P624