Conformational flexibility of C-glycosides: Experimental evidence of the existence of a Gauche-Gauche conformation around the glycosidic linkage for a lactose analogue

被引：26

作者：

Espinosa, JF ^{[1
]}

Dietrich, HJ ^{[1
]}

MartinLomas, M ^{[1
]}

Schmidt, RR ^{[1
]}

JimenezBarbero, J ^{[1
]}

机构：

[1] UNIV KONSTANZ,FAK CHEM,D-78434 CONSTANCE,GERMANY

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 09期

关键词：

D O I：

10.1016/0040-4039(95)02397-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The solution conformation of C-glycosides 3 and 4, presenting a hydroxyl group at the bridging position, has been determined by NMR and MM3* calculations. The conformation of 3 is similar to that of C-lactose, while that of 4 is rather different and shows a significant contribution of a conformer with a gauche disposition between C1'-05' and C1'-C2' bonds.

引用

收藏

页码：1467 / 1470

页数：4

相关论文

共 13 条

[1] MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].

ALLINGER, NL ;

YUH, YH ;

LII, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566

[2] THE USE OF THE AMBER FORCE-FIELD IN CONFORMATIONAL-ANALYSIS OF CARBOHYDRATE MOLECULES - DETERMINATION OF THE SOLUTION CONFORMATION OF METHYL ALPHA-LACTOSIDE BY NMR-SPECTROSCOPY, ASSISTED BY MOLECULAR MECHANICS AND DYNAMICS CALCULATIONS [J].

ASENSIO, JL ;

JIMENEZBARBERO, J .

BIOPOLYMERS, 1995, 35 (01) :55-73

[3] THE USE OF CVFF AND CFF91 FORCE-FIELDS IN CONFORMATIONAL-ANALYSIS OF CARBOHYDRATE MOLECULES - COMPARISON WITH AMBER MOLECULAR MECHANICS AND DYNAMICS CALCULATIONS FOR METHYL ALPHA-LACTOSIDE [J].

ASENSIO, JL ;

MARTINPASTOR, M ;

JIMENEZBARBERO, J .

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 1995, 17 (3-4) :137-148

[4] THE CONFORMATION OF 8-MEMBERED 3,2'-O-ISOPROPYLIDENE ACETALS OF SOME COMMON DISACCHARIDES [J].

BERNABE, M ;

FERNANDEZMAYORALAS, A ;

JIMENEZBARBERO, J ;

MARTINLOMAS, M ;

RIVERA, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (11) :1867-1873

[5] CONFORMATIONAL EQUILIBRIA OF 4-THIOMALTOSE AND NITROGEN ANALOGS OF MALTOSE IN AQUEOUS-SOLUTIONS [J].

BOCK, K ;

DUUS, JO ;

REFN, S .

CARBOHYDRATE RESEARCH, 1994, 253 :51-67

[6] CONFORMATIONAL MOBILITY OF OLIGOSACCHARIDES - EXPERIMENTAL-EVIDENCE FOR THE EXISTENCE OF AN ANTI CONFORMER OF THE GA1-BETA-1-3GLC-BETA-1-OME DISACCHARIDE [J].

DABROWSKI, J ;

KOZAR, T ;

GROSSKURTH, H ;

NIFANTEV, NE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (20) :5534-5539

[7]

DIETRICH H, 1994, LIEBIGS ANN CHEM, P975

[8] INTERNAL MOTIONS OF CARBOHYDRATES AS PROBED BY COMPARATIVE MOLECULAR MODELING AND NUCLEAR-MAGNETIC-RESONANCE OF ETHYL BETA-LACTOSIDE [J].

ENGELSEN, SB ;

PEREZ, S ;

BRACCINI, I ;

DUPENHOAT, CH .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1995, 16 (09) :1096-1119

[9] EXPERIMENTAL AND THEORETICAL EVIDENCES OF CONFORMATIONAL FLEXIBILITY OF C-GLYCOSIDES - NMR ANALYSIS AND MOLECULAR MECHANICS CALCULATIONS OF C-LACTOSE AND ITS O-ANALOG [J].

ESPINOSA, JF ;

MARTINPASTOR, M ;

ASENSIO, JL ;

DIETRICH, H ;

MARTINLOMAS, M ;

SCHMIDT, RR ;

JIMENEZBARBERO, J .

TETRAHEDRON LETTERS, 1995, 36 (35) :6329-6332

[10]

ESPINOSA JF, IN PRESS J ANGEW CHE