Conformational behavior of sucrose and its deoxy analog in water as determined by NMR and molecular modeling

Penhoat, C. Hervé Du; Imberty, Anne; Roques, Nicolas; Michon, V.; Mentech, J.; Descotes, G.; Pérez, Serge

doi:10.1021/ja00010a014

Cited by 94 publications

(42 citation statements)

References 3 publications

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“…As described previously (Hervé du Penhoat et al, 1991;Poppe and van Halbeek, 1992), for sucrose in solution, inter-residue NOEs are observed between protons H1-g and H1-f, H1-g and H4-f, and H1-g and H6-f (Fig. 7b).…”

Section: Resultssupporting

confidence: 83%

“…The torsion angles for the primary hydroxyl groups g, f, and f have a GG, GT, and GG orientation, respectively. The puckering parameters of both fructose residues have values of Q ϭ 0.47 and ϭ 260°, which corresponds to a shape between an E 3 envelope and a 4 T 3 twist, both which are observed in sucrose-containing crystalline compounds (Hervé du Penhoat et al, 1991). Since both sucrose moieties are so similar, only the first one will be described in the following parts of the paper.…”

Section: Resultsmentioning

confidence: 99%

“…flexible in dilute solution (Hervé du Penhoat et al, 1991;Poppe and Van Halbeek, 1992), but its interactions with protein receptors have never been investigated. We report here the first x-ray structure of sucrose complexed with a protein.…”

Section: Figmentioning

confidence: 99%

“…The glucose residue located in the lentil lectin binding site was extended to an ␣-D-Glcp (132) furanosyl group. The starting geometry of sucrose was given a low energy conformation (⌽ ϭ 110°and ⌿ ϭ Ϫ60°) as described previously (Hervé du Penhoat et al, 1991). In order to save computing time, only part of the protein was considered in the calculations.…”

Section: Molecular Modelingmentioning

confidence: 99%

“…Each primary hydroxyl group of fructofuranose was given its two preferred staggered orientations, i.e. GG and GT for f and GG and TG for f, as determined by screening all the sucrose-containing crystalline structures (Hervé du Penhoat et al, 1991). The hydroxymethyl group of glucose always kept its GG orientation.…”

Section: Molecular Modelingmentioning

confidence: 99%

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NMR, Molecular Modeling, and Crystallographic Studies of Lentil Lectin-Sucrose Interaction

Casset¹,

Hamelryck

Loris

et al. 1995

Journal of Biological Chemistry

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The conformational features of sucrose in the combining site of lentil lectin have been characterized through elucidation of a crystalline complex at 1.9-Å resolution, transferred nuclear Overhauser effect experiments performed at 600 Mhz, and molecular modeling. In the crystal, the lentil lectin dimer binds one sucrose molecule per monomer. The locations of 229 water molecules have been identified. NMR experiments have provided 11 transferred NOEs. In parallel, the docking study and conformational analysis of sucrose in the combining site of lentil lectin indicate that three different conformations can be accommodated. Of these, the orientation with lowest energy is identical with the one observed in the crystalline complex and provides good agreement with the observed transferred NOEs. These structural investigations indicate that the bound sucrose has a unique conformation for the glycosidic linkage, close to the one observed in crystalline sucrose, whereas the fructofuranose ring remains relatively flexible and does not exhibit any strong interaction with the protein. Major differences in the hydrogen bonding network of sucrose are found. None of the two inter-residue hydrogen bonds in crystalline sucrose are conserved in the complex with the lectin. Instead, a water molecule bridges hydroxyl groups O2-g and O3-f of sucrose.

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Section: Resultssupporting

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Figmentioning

confidence: 99%

Section: Molecular Modelingmentioning

confidence: 99%

Section: Molecular Modelingmentioning

confidence: 99%

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NMR, Molecular Modeling, and Crystallographic Studies of Lentil Lectin-Sucrose Interaction

Casset¹,

Hamelryck

Loris

et al. 1995

Journal of Biological Chemistry

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Sugar, Sugar Derivatives

Khan

Konowicz

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Sucrose is an important food commodity. Its potential as a raw material for chemicals has long been recognized, but the actual commercial success has been limited. Significant progress toward the understanding of its chemistry has been made in recent years. This has led to the development of such commercial products as sucralose, a high intensity sweetener; sucrose fatty acid esters as food additives or emulsifiers and surfactants; and Palatinit and Actilite as noncariogenic bulk sweeteners. The application of reactions such as esterification, etherification, sulfonylation, S N 2 displacement reactions, halogenation, oxidation, and amination has resulted in a large number of well‐characterized sucrose derivatives. The potential of these derivatives as biologically active materials, polymer intermediates, food additives, as well as other industrial applications, awaits development.

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Multiple-field carbon-13 and proton relaxation in sucrose in viscous solution

2000

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Measurements of carbon‐13 spin–lattice and spin–spin relaxation rates as well as nuclear Overhauser enhancement (NOE) were combined with selected proton cross‐relaxation measurements for sucrose in a viscous cryosolvent, D2O–DMSO, at several magnetic fields and two temperatures. The results, which were outside the extreme narrowing regime, were interpreted using the Lipari–Szabo formalism. All the carbon relaxation data and the proton cross‐relaxation rates give a consistent description, demonstrating that the two sugar residues display a similar and highly limited internal mobility and that the hydroxymethyl groups are more mobile. Our combined carbon and proton data do not give evidence for flexibility of the glycosidic linkage in sucrose. Copyright © 2000 John Wiley & Sons, Ltd.

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Conformational behavior of sucrose and its deoxy analog in water as determined by NMR and molecular modeling

Cited by 94 publications

References 3 publications

NMR, Molecular Modeling, and Crystallographic Studies of Lentil Lectin-Sucrose Interaction

NMR, Molecular Modeling, and Crystallographic Studies of Lentil Lectin-Sucrose Interaction

Sugar, Sugar Derivatives

Multiple-field carbon-13 and proton relaxation in sucrose in viscous solution

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