CONFORMATIONAL-ANALYSIS OF NITRILIUM INTERMEDIATES IN GLYCOSYLATION REACTIONS

被引：117

作者：

BRACCINI, I ^{[1
]}

DEROUET, C ^{[1
]}

ESNAULT, J ^{[1
]}

DUPENHOAT, CH ^{[1
]}

MALLET, JM ^{[1
]}

MICHON, V ^{[1
]}

SINAY, P ^{[1
]}

机构：

[1] ECOLE NORMALE SUPER,CHIM LAB,URA 1110,24 RUE LHOMOND,F-75231 PARIS,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1993年 / 246卷

关键词：

D O I：

10.1016/0008-6215(93)84021-W

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：

In order to shed light on the stereoselectivity of acetonitrile-mediated glycosylation reactions, the nitrilium intermediates have been generated at -30-degrees-C in acetonitrile-d3 and studied by H-1, C-13, and N-15 NMR spectroscopy. Conjointly, molecular modeling of the intermediates by molecular mechanics has been performed with the CHARMm force field. All the evidence suggests that only nitrilium derivatives with the a configuration are formed.

引用

页码：23 / 41

页数：19

共 47 条

[1] BOCK K, 1982, ANNU REP NMR SPECTRO, V13, P1
[2] BOUCHOUX G, 1983, NOUV J CHIM, V7, P385
[3] A GROUP ELECTRONEGATIVITY METHOD WITH PAULING UNITS
BRATSCH, SG
[J]. JOURNAL OF CHEMICAL EDUCATION, 1985, 62 (02) : 101 - 103
[4] CONFORMATIONAL-ANALYSIS OF THE SIALYL-ALPHA-(2-]3/6)N-ACETYLLACTOSAMINE STRUCTURAL ELEMENT OCCURRING IN GLYCOPROTEINS, BY TWO-DIMENSIONAL NOE H-1-NMR SPECTROSCOPY IN COMBINATION WITH ENERGY CALCULATIONS BY HARD-SPHERE EXO-ANOMERIC AND MOLECULAR MECHANICS FORCE-FIELD WITH HYDROGEN-BONDING POTENTIAL
BREG, J
KROONBATENBURG, LMJ
STRECKER, G
MONTREUIL, J
VLIEGENTHART, JFG
[J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1989, 178 (03): : 727 - 739
[5] STEREOCHEMICAL SIGNIFICANCE OF LONG-RANGE PROTON SPIN COUPLING CONSTANT OF SIGMA-FRAGMENT H-C-C-C-H
BYSTROV, VF
STEPANYA.AU
[J]. JOURNAL OF MOLECULAR SPECTROSCOPY, 1966, 21 (03) : 241 - &
[6] DETERMINATION OF THE CONFORMATION OF LEWIS BLOOD-GROUP OLIGOSACCHARIDES BY SIMULATION OF 2-DIMENSIONAL NUCLEAR OVERHAUSER DATA
CAGAS, P
BUSH, CA
[J]. BIOPOLYMERS, 1990, 30 (11-12) : 1123 - 1138
[7] Experimental structure determination of oligosaccharides
Carver, Jeremy P.
[J]. CURRENT OPINION IN STRUCTURAL BIOLOGY, 1991, 1 (05) : 716 - 720
[8] PROTON SPIN-LATTICE RELAXATION RATES IN THE STRUCTURAL-ANALYSIS OF CARBOHYDRATE MOLECULES IN SOLUTION
DAIS, P
PERLIN, AS
[J]. ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1987, 45 : 125 - 168
[9] DUPENHOAT CH, 1991, J AM CHEM SOC, V113, P3720
[10] FRENCH AD, 1990, ASC S SER, V430

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