Octa-O-acetyl-β,β-thiotrehalose

Färnbäck, Magnus; Eriksson, Lars; Widmalm, Göran

doi:10.1107/s0108768100003682

Cited by 3 publications

(5 citation statements)

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“…In our previous studies of carbohydrates in the solid state we have employed both NMR spectroscopy and X-ray crystallography techniques. To obtain information on molecular structure and dynamics, we will continue to utilize these complementary methods and, in the case of solid-state NMR, develop novel experiments and analytical procedures for a continued and focused investigation of carbohydrate systems being part of or models for those in biological systems such as glycolipids or glycoproteins.…”

Section: Discussionmentioning

confidence: 99%

Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by ¹³C Solid-State NMR

et al. 2003

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Local motions in the cyanogenic glycoside amygdalin have been characterized by variable-temperature 13C solid-state NMR spectroscopy. Carbon-13 chemical shift tensors and 1H−13C dipolar couplings were measured by advanced magic-angle spinning NMR techniques over the temperature range 0−90 °C. The main conclusions from our study are that the phenyl ring exhibits thermally activated dynamics about the para axis, whereas the glucopyranosyl residues remain immobile upon heating. It was also found that sample heating is accompanied by loss of water. The experimental results were complemented by quantum chemical calculations of the 13C chemical shift tensors, which were utilized in the analysis of the experimental NMR parameters.

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Section: Discussionmentioning

confidence: 99%

Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by ¹³C Solid-State NMR

et al. 2003

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“…(See the paragraph on Nomenclature in Methods, Table , and Figure . ) ,− The lowest value of either φ or φ‘ in crystalline trehalose moieties is 45°, in a salt complex of allo-trehalose . The highest is 91° in a heavily derivatized example .…”

Section: Introductionmentioning

confidence: 95%

Quantum Mechanics Studies of the Intrinsic Conformation of Trehalose

et al. 2002

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To resolve controversies over the intrinsic shape of the disaccharide α,α-trehalose and the magnitude of solvent effects, energy surfaces have been computed at different levels of molecular orbital and density functional theory. All quantum mechanical (QM) levels agree that the gauche linkage conformations observed by experimental crystallographic and solution studies are 5−7 kcal/mol lower in energy than that of the trans shape. This is quite different than the findings of the two most recent classical force field studies. In those projects, the trans shape was preferred by 3.3 kcal/mol, and it was inferred that a strong solvent effect was responsible for the gauche experimental conformations. In the QM work, a strong solvent effect is not needed to explain the preference for the gauche form because the trans shapes already have higher energy. A QM continuum model of aqueous solvation has only small effects on the torsional energy surface. The best rationalization of 24 values of the linkage torsion angles from small-molecule crystal structures is provided by HF/6-311++G**//B3LYP/6-31G* theory, a level that under-predicts the strength of hydrogen bonds.

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“…The spectrum shows two strong peaks from the labeled 13 C sites as well as weaker signals from the natural abundance spins. The small isotropic shift difference of 0.9 ppm between the two strong 13 C peaks is due to the asymmetry of the molecules in the crystal structure (28). Figure 2b shows a double-quantum-filtered spectrum of the same compound under identical conditions, obtained using the C7 pulse sequence (32).…”

Section: Solid-state Nmrmentioning

confidence: 97%

“…In the present case, Moleculix was used to construct a graphical model of the molecule I using the X-ray coordinates (28). The torsional angles φ and φ were then varied, keeping bond lengths and bond angles fixed.…”

Section: Simulationsmentioning

confidence: 99%

“…The glycosidic conformation is defined by the two torsional angles φ OCSC (henceforth referred to as φ), and φ CSC O (henceforth referred to as φ ). The substance I was chosen because the synthesis is relatively straightforward and because the crystal structure has been determined by X-ray diffraction (28). The X-ray structure corresponds to the conformation (φ, φ ) = (−67.2…”

Section: Introductionmentioning

confidence: 99%

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Conformation of the Glycosidic Linkage in a Disaccharide Investigated by Double-Quantum Solid-State NMR

Ravindranathan

Karlsson

Lycknert³

et al. 2001

Journal of Magnetic Resonance

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Octa-O-acetyl-β,β-thiotrehalose

Cited by 3 publications

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Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by ¹³C Solid-State NMR

Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by ¹³C Solid-State NMR

Quantum Mechanics Studies of the Intrinsic Conformation of Trehalose

Conformation of the Glycosidic Linkage in a Disaccharide Investigated by Double-Quantum Solid-State NMR

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Octa-O-acetyl-β,β-thiotrehalose

Cited by 3 publications

References 0 publications

Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by 13C Solid-State NMR

Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by 13C Solid-State NMR

Quantum Mechanics Studies of the Intrinsic Conformation of Trehalose

Conformation of the Glycosidic Linkage in a Disaccharide Investigated by Double-Quantum Solid-State NMR

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Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by ¹³C Solid-State NMR

Probing Segmental Mobility in the Cyanogenic Glycoside Amygdalin by ¹³C Solid-State NMR