Structure of 6-kestose monohydrate, C18H31O16.H2O

Ferretti, Valeria; Bertolasi, Valerio; Gilli, Gastone; Accorsi, Carla Alberta

doi:10.1107/s0108270184004765

Cited by 28 publications

(6 citation statements)

References 9 publications

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“…The Fru-(2 ! 1)-Glc in INU10 linkages were set to u (O5(G)-C1(G)-O1(G)-C2(F)) at 808 and c (C1(G)-O1(G)-C2(F)-C3(F)) at ÿ1708 in agreement with the crystallographic data of 6-kestose (Ferretti et al, 1983). This research was supported by an Earth and Live Sciences (ALW) and chemical sciences (CW) grant with financial aid from the Dutch Organization for Scientific Research (NWO).…”

Section: Adaptive Umbrella Samplingmentioning

confidence: 97%

“…Molecular understanding of the interaction of inulin and levan with lipids requires knowledge of the spatial structure of the carbohydrates. Some work has been done on the conformations in crystal structures of smaller fructan molecules and by molecular mechanics calculations in vacuo (Calub et al, 1990;Ferretti et al, 1983;French et al, 1997;Jeffrey and Park, 1972;Liu and Waterhouse, 1992;Waterhouse et al, 1991). However, little is known of the conformation of larger structures in solution, and therefore MD simulations of model compounds in the presence of water molecules were performed.…”

Section: Molecular Dynamicsmentioning

confidence: 99%

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Structural Requirements of the Fructan-Lipid Interaction

Vereyken

Kuik

Evers

et al. 2003

Biophysical Journal

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Fructans are a group of fructose-based oligo- and polysaccharides. They are proposed to be involved in membrane protection of plants during dehydration. In accordance with this hypothesis, they show an interaction with hydrated lipid model systems. However, the structural requirements for this interaction are not known both with respect to the fructans as to the lipids. To get insight into this matter, the interaction of several inulins and levan with lipids was investigated using a monomolecular lipid system or the MC 540 probe in a bilayer system. MD was used to get conformational information concerning the polysaccharides. It was found that levan-type fructan interacted comparably with model membranes composed of glyco- or phospholipids but showed a preference for lipids with a small headgroup. Furthermore, it was found that there was an inulin chain-length-dependent interaction with lipids. The results also suggested that inulin-type fructan had a more profound interaction with the membrane than levan-type fructan. MD simulations indicated that the favorable conformation for levan is a helix, whereas inulin tends to form random coil structures. This suggests that flexibility is an important determinant for the fructan-lipid interaction.

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Section: Adaptive Umbrella Samplingmentioning

confidence: 97%

Section: Molecular Dynamicsmentioning

confidence: 99%

Structural Requirements of the Fructan-Lipid Interaction

Vereyken

Kuik

Evers

et al. 2003

Biophysical Journal

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“…In the case of the disaccharides maltose and sucrose, the initial structures were taken from the Chemistry, Structures & 3D Molecules Web site . The Crystallographic Information Files of the trisaccharides 1-kestose (kestos.cif), 6-kestose (celgij.cif), and raffinose (rafino.cif) from the Cambridge Structural Database were used to construct their initial geometries. The conversion to Cartesian coordinates was made with the visualization software Mercury CSD 2.3 …”

Section: Computational Detailsmentioning

confidence: 99%

Carbohydrates and Their Free Radical Scavenging Capability: A Theoretical Study

Hernández-Marín

Martı́nez

2012

J. Phys. Chem. B

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A density functional theory (DFT) study on the free radical (OH(•) and OOH(•)) scavenging properties of some mono- and polysaccharides is presented. Two mechanisms, single electron transfer (SET) and hydrogen atom transfer (HAT), are considered. The former mechanism is studied by making use of the vertical ionization energy and vertical electron affinity of the radicals and carbohydrates. It is confirmed that the SET mechanism is not plausible to occur. With respect to the HAT, not only does the OH(•) radical react preferably with one hydrogen atom bonded to one carbon atom, but also the reaction with a hydrogen atom bonded to an oxygen is possible. Finally, it is suggested that the carbohydrates are not able to directly scavenge OOH(•).

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“…The structures of fructan trisaccharides have been defined by X-ray crystallography and 13 C NMR , of isolated compounds. Structures of a number of fructan oligomers have been determined by classical methylation and/or hydrolysis procedures or NMR, following isolation from the matrix, but these characterizing features are not readily applicable to chromatographic analysis of crude or minimally cleaned up samples.…”

mentioning

confidence: 99%

Linear Ion Trap MSⁿ of Enzymatically Synthesized 13C-Labeled Fructans Revealing Differentiating Fragmentation Patterns of β (1-2) and β (1-6) Fructans and Providing a Tool for Oligosaccharide Identification in Complex Mixtures

et al. 2012

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Fructans are polymeric carbohydrates, which play important roles as plant reserve carbohydrates and stress protectants, and are beneficial for human health and animal production. Fructans are formed by the addition of β-d-fructofuranosyl units to sucrose, leading to very complex mixtures of 1-kestose based inulins, 6-kestose linked levans, and 6G-kestose derived neoseries inulins and levans in cool season grasses such as Lolium perenne. The identification of isomeric fructan oligomers in chromatographic analysis of crude plant extracts is often hampered by the lack of authentic standards, and unambiguous peak assignment usually requires time-consuming analyses of purified fructan oligomers. We have developed a LC-MS(n) method for the separation and detection of fructan isomers and present here evidence for specific MS(n) fragmentation patterns associated with β 1-2 (inulins) and β 2-6 (levans) fructans. LC-MS(n) analysis of (13)C labeled fructan oligomers produced by L. perenne fructosyltransferases expressed in yeast has enabled us to account for the observed fragmentation patterns in terms of preferential cleavage of the glycosidic bond between O- and fructose C2 in both inulins and levans and to differentiate reducing-end from nonreducing end cross ring cleavages in levans. We propose that higher order MS fragmentation patterns can be used to distinguish between the two major classes of fructan, i.e., inulins and levans, without the need for authentic standards.

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Structure of 6-kestose monohydrate, C18H31O16.H2O

Cited by 28 publications

References 9 publications

Structural Requirements of the Fructan-Lipid Interaction

Structural Requirements of the Fructan-Lipid Interaction

Carbohydrates and Their Free Radical Scavenging Capability: A Theoretical Study

Linear Ion Trap MSⁿ of Enzymatically Synthesized 13C-Labeled Fructans Revealing Differentiating Fragmentation Patterns of β (1-2) and β (1-6) Fructans and Providing a Tool for Oligosaccharide Identification in Complex Mixtures

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Structure of 6-kestose monohydrate, C18H31O16.H2O

Cited by 28 publications

References 9 publications

Structural Requirements of the Fructan-Lipid Interaction

Structural Requirements of the Fructan-Lipid Interaction

Carbohydrates and Their Free Radical Scavenging Capability: A Theoretical Study

Linear Ion Trap MSn of Enzymatically Synthesized 13C-Labeled Fructans Revealing Differentiating Fragmentation Patterns of β (1-2) and β (1-6) Fructans and Providing a Tool for Oligosaccharide Identification in Complex Mixtures

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Linear Ion Trap MSⁿ of Enzymatically Synthesized 13C-Labeled Fructans Revealing Differentiating Fragmentation Patterns of β (1-2) and β (1-6) Fructans and Providing a Tool for Oligosaccharide Identification in Complex Mixtures