Excellent enantio-selective enclathration of (2R,3S)-3-methyl-2-pentanol in channel-like cavity of 3-epideoxycholic acid, interpreted by the four-location model for chiral recognition

被引:25
作者
Kato, K [1 ]
Aburaya, K [1 ]
Miyake, Y [1 ]
Sada, K [1 ]
Tohnai, N [1 ]
Miyata, M [1 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Mat & Life Sci, Suita, Osaka 5650871, Japan
关键词
D O I
10.1039/b309755b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pure ( 2R, 3S)- 3- methyl- 2- pentanol is resolved from the racemates by a steroidal host; the interpretation of the recognition mechanism based on the crystal structure reveals that CH/ O interaction between the host and guest plays a decisive role in enantio- selective enclathration of the small aliphatic secondary alcohol.
引用
收藏
页码:2872 / 2873
页数:2
相关论文
共 25 条
[1]  
Aoki Y, 2000, ENANTIOMER, V5, P95
[2]  
BETLEY R, 1978, NATURE, V276, P673
[3]  
BOSE AK, 1973, TETRAHEDRON LETT, P1619
[4]   Structures of three inclusion compounds of cholanamide with either (S)-enantiomer, (R)-enantiomer or an optically resolved mixture of butan-2-ol [J].
Briozzo, P ;
Kondo, T ;
Sada, K ;
Miyata, M ;
Miki, K .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1996, 52 :728-733
[5]   THE RESOLUTION OF SECONDARY AND TERTIARY ALCOHOLS CONTAINING THE PYRIDYL GROUP [J].
DAVIES, AG ;
KENYON, J ;
THAKER, K .
JOURNAL OF THE CHEMICAL SOCIETY, 1956, (SEP) :3394-3397
[6]  
INGERSOLL AW, 1944, ORG REACTIONS, V2, P380
[7]   Interpretation of enantioresolution in nordeoxycholic acid channels based on the four-location model [J].
Kato, K ;
Aoki, Y ;
Sugahara, M ;
Tohnai, N ;
Sada, K ;
Miyata, M .
CHIRALITY, 2003, 15 (01) :53-59
[8]   Optical resolution of racemic alcohols by diastereoisomeric complex formation with O,O'-dibenzoyl-(2R,3R)-tartaric acid; The crystal structure of the (-)-(1R,2S,5R)-menthol center dot O,O'-dibenzoyl-(2R,3R)-tartaric acid complex [J].
Kozma, D ;
Bocskei, Z ;
Kassai, C ;
Simon, K ;
Fogassy, E .
CHEMICAL COMMUNICATIONS, 1996, (06) :753-754
[9]   Structural biology - A new model for protein stereospecificity [J].
Mesecar, AD ;
Koshland, DE .
NATURE, 2000, 403 (6770) :614-615
[10]   NEW CHANNEL-TYPE INCLUSION COMPOUND OF STEROIDAL BILE-ACID - STRUCTURE OF A 1-1 COMPLEX BETWEEN CHOLIC-ACID AND ACETOPHENONE [J].
MIKI, K ;
MASUI, A ;
KASAI, N ;
MIYATA, M ;
SHIBAKAMI, M ;
TAKEMOTO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (19) :6594-6596