Cyclodextrin-accelerated cleavage of phenyl esters: is it the 2-hydroxy or the 3-hydroxy that promotes the acyl transfer?

被引:14
作者
Fukudome, M [1 ]
Okabe, Y [1 ]
Yuan, DQ [1 ]
Fujita, K [1 ]
机构
[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan
关键词
D O I
10.1039/a902123j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Both 2- and 3-monothiocyclodextrins have been synthesized and used in probing the mechanism of cyclodextrin-mediated cleavage of phenyl esters, showing that the 3-thiols are much more effective than the 2-thiols in promoting the acyl transfer.
引用
收藏
页码:1045 / 1046
页数:2
相关论文
共 18 条
[1]  
Bender M.L., 1978, Cyclodextrin Chemistry
[2]   Enantioselective influence of cyclodextrins on cleavage of chiralic esters [J].
Beyrich, T ;
Jira, T ;
Beyer, C .
CHIRALITY, 1995, 7 (07) :560-564
[3]   OPTIMIZATION OF METALLOCENE SUBSTRATES FOR BETA-CYCLODEXTRIN REACTIONS [J].
BRESLOW, R ;
TRAINOR, G ;
UENO, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2739-2744
[4]   Biomimetic reactions catalyzed by cyclodextrins and their derivatives [J].
Breslow, R ;
Dong, SD .
CHEMICAL REVIEWS, 1998, 98 (05) :1997-2011
[5]   ADDITIONAL FLEXIBILITY SOLVES THE LEAVING GROUP-PROBLEM IN CYCLODEXTRIN ACYLATION [J].
BRESLOW, R ;
CHUNG, S .
TETRAHEDRON LETTERS, 1990, 31 (05) :631-634
[6]   IMPROVED ACYLATION RATES WITHIN CYCLODEXTRIN COMPLEXES FROM FLEXIBLE CAPPING OF THE CYCLODEXTRIN AND FROM ADJUSTMENT OF THE SUBSTRATE GEOMETRY [J].
BRESLOW, R ;
CZARNIECKI, MF ;
EMERT, J ;
HAMAGUCHI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (02) :762-770
[7]   TRANSAMINATIONS BY PYRIDOXAMINE SELECTIVELY ATTACHED AT C-3 IN BETA-CYCLODEXTRIN [J].
BRESLOW, R ;
CZARNIK, AW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (05) :1390-1391
[8]   Regiospecifically multifunctional beta-cyclodextrins with two or three glucose residues bearing imidazolyl groups at the C3 positions [J].
Chen, WH ;
Yuan, DQ ;
Fujita, K .
TETRAHEDRON LETTERS, 1997, 38 (26) :4599-4602
[9]   Methods for selective modifications of cyclodextrins [J].
Khan, AR ;
Forgo, P ;
Stine, KJ ;
D'Souza, VT .
CHEMICAL REVIEWS, 1998, 98 (05) :1977-1996
[10]   EFFECT OF PRESSURE ON 2 CYCLODEXTRIN-PROMOTED ESTER HYDROLYSES [J].
LENOBLE, WJ ;
SRIVASTAVA, S ;
BRESLOW, R ;
TRAINOR, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2745-2748