EXPERIMENTAL AND THEORETICAL EVIDENCES OF CONFORMATIONAL FLEXIBILITY OF C-GLYCOSIDES - NMR ANALYSIS AND MOLECULAR MECHANICS CALCULATIONS OF C-LACTOSE AND ITS O-ANALOG

被引：42

作者：

ESPINOSA, JF

MARTINPASTOR, M

ASENSIO, JL

DIETRICH, H

MARTINLOMAS, M

SCHMIDT, RR

JIMENEZBARBERO, J

机构：

[1] CSIC,INST QUIM ORGAN,DEPT QUIM ORGAN BIOL,CARBOHIDRATOS GRP,E-28006 MADRID,SPAIN

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 35期

关键词：

D O I：

10.1016/0040-4039(95)01223-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

NMR data (NOEs and coupling constants) and MM3* molecular mechanics calculations have allowed to demonstrate that the conformational behaviour of C-lactose is different of its O-analogue. The glycosidic linkages, particularly the C-aglyconic bond, present a high degree of flexibility and, therefore, the conformational entropy of C-lactose is higher than that of its O-counterpart.

引用

页码：6329 / 6332

页数：4

共 22 条

[1] MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1.
ALLINGER, NL
YUH, YH
LII, JH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) : 8551 - 8566
[2] Asensio JA, UNPUB
[3] 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
ASENSIO, JL
JIMENEZBARBERO, J
[J]. BIOPOLYMERS, 1995, 35 (01) : 55 - 73
[4] ASENSIO JL, 1995, IN PRESS INT J BIOL
[5] A CONFORMATIONAL STUDY OF HYDROXYMETHYL GROUPS IN CARBOHYDRATES INVESTIGATED BY H-1-NMR SPECTROSCOPY
BOCK, K
DUUS, JO
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (04) : 513 - 543
[6] THE PREFERRED CONFORMATION OF OLIGOSACCHARIDES IN SOLUTION INFERRED FROM HIGH-RESOLUTION NMR DATA AND HARD-SPHERE EXO-ANOMERIC CALCULATIONS
BOCK, K
[J]. PURE AND APPLIED CHEMISTRY, 1983, 55 (04) : 605 - 622
[7] DIETRICH H, 1994, LIEBIGS ANN CHEM, P975
[8] DIETRICH H, 1994, CARBOHYDR LETT, V1, P115
[9] CONFORMATIONAL-ANALYSIS OF THE ANOMERIC FORMS OF SOPHOROSE, LAMINARABIOSE, AND CELLOBIOSE USING MM3
DOWD, MK
FRENCH, AD
REILLY, PJ
[J]. CARBOHYDRATE RESEARCH, 1992, 233 : 15 - 34
[10] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION
HAASNOOT, CAG
DELEEUW, FAAM
ALTONA, C
[J]. TETRAHEDRON, 1980, 36 (19) : 2783 - 2792

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