Hydrogen bonding and cooperativity effects on the assembly of carbohydrates

被引:30
作者
de la Paz, ML [1 ]
Jiménez-Barbero, J [1 ]
Vicent, C [1 ]
机构
[1] CSIC, Inst Quim Organ, Dept Quim Organ Biol, E-28006 Madrid, Spain
关键词
D O I
10.1039/a708386f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The effect of intramolecular hydrogen bonds on the cooperative assembly of carbohydrate derivatives has been evaluated; the 1,3-diaxial OH ... OH intramolecular hydrogen bond is at the origin of the dimerization of diol 1; and one intermolecular OH ... OH bond accounts for 2.5 kcal mol(-1) in CDCl3 and 3 kcal mol(-1) in CDCl3-CCl4.
引用
收藏
页码:465 / 466
页数:2
相关论文
共 21 条
[1]   COOPERATIVE INTRAMOLECULAR HYDROGEN-BONDING IN GLUCOSE AND MALTOSE [J].
CHRISTOFIDES, JC ;
DAVIES, DB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (01) :97-102
[2]   Isotopic perturbation of intramolecular hydrogen bonds in rigid 1,3-diols: NMR studies reveal unusually large equilibrium isotope effects [J].
Craig, BN ;
Janssen, MU ;
Wickersham, BM ;
Rabb, DM ;
Chang, PS ;
OLeary, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9610-9613
[3]   Conformational restriction by intramolecular hydrogen bonding. Carbohydrate-carbohydrate self-assembly. [J].
delaPaz, ML ;
Ellis, G ;
Penades, S ;
Vicent, C .
TETRAHEDRON LETTERS, 1997, 38 (09) :1659-1662
[4]   A QUANTITATIVE STUDY OF STRUCTURAL EFFECTS ON THE SELF-ASSOCIATION OF ALCOHOLS [J].
FRANGE, B ;
ABBOUD, JLM ;
BENAMOU, C ;
BELLON, L .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4553-4557
[5]  
FRANK HS, 1957, DISCUSS FARADAY SOC, P133
[6]   SOLVENT INFLUENCE ON THE STABILITY OF THE PEPTIDE HYDROGEN-BOND - A SUPRAMOLECULAR COOPERATIVE EFFECT [J].
GUO, H ;
KARPLUS, M .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (29) :7104-7105
[7]   FACTORS GOVERNING INFLUENCE OF A 1ST HYDROGEN-BOND ON FORMATION OF A 2ND ONE BY SAME MOLECULE OR ION [J].
HUYSKENS, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (08) :2578-2582
[8]  
Jeffrey G.A., 1991, HYDROGEN BONDING BIO, DOI [10.1007/978-3-642-85135-3, DOI 10.1007/978-3-642-85135-3]
[10]   QUANTITATIVE INFRARED SPECTROSCOPIC INVESTIGATIONS OF HYDROGEN-BOND COOPERATIVITY [J].
KLEEBERG, H ;
KLEIN, D ;
LUCK, WAP .
JOURNAL OF PHYSICAL CHEMISTRY, 1987, 91 (12) :3200-3203