CRYSTAL-STRUCTURE OF 6-0-[(R)-2-HYDROXYPROPYL]CYCLOMALTOHEPTAOSE AND 6-0-[(S)-2-HYDROXYPROPYL]CYCLOMALTOHEPTAOSE

被引:36
作者
HARATA, K
RAO, CT
PITHA, J
机构
[1] RES INST POLYMERS & TEXT,TSUKUBA,IBARAKI 305,JAPAN
[2] NIA,GRC,BALTIMORE,MD 21224
关键词
D O I
10.1016/0008-6215(93)84243-Y
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Crystal structures of 6-O-[(R)-2-hydroxypropyl]- and 6-O-[(S)-2-hydroxypropyl)-cyclomaltoheptaose were determined by X-ray analysis. In both structures, the 2-hydroxypropyl group is inserted into the macrocyclic cavity of the next molecule related by the two-fold screw axis, and a helically extended polymeric structure is formed by repetition of the intermolecular inclusion. The hydroxyl group of the substituent group penetrates through the macrocyclic ring from the secondary hydroxyl side and is linked to an HO-6 group by a hydrogen bond. Comparison of intermolecular contacts of the substituent group indicates that the (S)-2-hydroxypropyl group is better fitted to the cavity than the (R)-2-hydroxypropyl group.
引用
收藏
页码:83 / 98
页数:16
相关论文
共 19 条
[1]  
Duchene D, 1991, NEW TRENDS CYCLODEXT, P55
[2]   STRUCTURE OF 6-O-ALPHA-D-GLUCOPYRANOSYL ALPHA-CYCLODEXTRIN.8H2O [J].
FUJIWARA, T ;
TANAKA, N ;
HAMADA, K ;
KOBAYASHI, S .
CHEMISTRY LETTERS, 1989, (07) :1131-1134
[3]   CRYSTAL-STRUCTURES OF INCLUSION COMPLEXES OF BETA-CYCLODEXTRIN WITH (S)-(+)-FENOPROFEN AND (R)-(-)-FENOPROFEN [J].
HAMILTON, JA ;
CHEN, LY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (13) :4379-4391
[4]   CRYSTAL-STRUCTURE OF 2-O-[(S)-2-HYDROXYPROPYL]CYCLOMALTOHEPTAOSE [J].
HARATA, K ;
RAO, CT ;
PITHA, J ;
FUKUNAGA, K ;
UEKAMA, K .
CARBOHYDRATE RESEARCH, 1991, 222 :37-45
[5]   THE STRUCTURE OF THE CYCLODEXTRIN COMPLEX .19. CRYSTAL-STRUCTURES OF HEXAKIS(2,3,6-TRI-O-METHYL)-ALPHA-CYCLODEXTRIN COMPLEXES WITH (S)-MANDELIC AND (R)-MANDELIC ACID - CHIRAL RECOGNITION THROUGH THE INDUCED-FIT CONFORMATIONAL CHANGE OF THE MACROCYCLIC RING [J].
HARATA, K ;
UEKAMA, K ;
OTAGIRI, M ;
HIRAYAMA, F .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (02) :497-502
[6]  
HARATA K, 1984, J INCLUSION PHENOM, V2, P583, DOI DOI 10.1007/978-94-009-5376-5_62
[7]   STRUCTURAL STUDY OF MONOSUBSTITUTED BETA-CYCLODEXTRINS - CRYSTAL-STRUCTURES OF PHENYLTHIO-BETA-CYCLODEXTRIN AND PHENYLSULPHINYL-BETA-CYCLODEXTRIN AND SPECTROSCOPIC STUDY OF RELATED-COMPOUNDS IN AQUEOUS-SOLUTION [J].
KAMITORI, S ;
HIROTSU, K ;
HIGUCHI, T ;
FUJITA, K ;
YAMAMURA, H ;
IMOTO, T ;
TABUSHI, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (01) :7-14
[8]  
LEBAS G, 1984, J INCLUSION PHENOM, V2, P861
[9]   SYNTHESIS OF SOME 2-O-(2-HYDROXYALKYL) AND 2-O-(2,3-DIHYDROXYALKYL) DERIVATIVES OF CYCLOMALTOHEPTAOSE [J].
LINDBERG, B ;
LINDBERG, J ;
PITHA, J ;
RAO, CT ;
HARATA, K .
CARBOHYDRATE RESEARCH, 1991, 222 :113-119
[10]   CRYSTAL AND MOLECULAR-STRUCTURE OF CYCLOHEPTA-AMYLOSE DODECAHYDRATE [J].
LINDNER, K ;
SAENGER, W .
CARBOHYDRATE RESEARCH, 1982, 99 (02) :103-115