Topic
Pyranose
About: Pyranose is a research topic. Over the lifetime, 1619 publications have been published within this topic receiving 35348 citations. The topic is also known as: pyranoses & hexopyranose.
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TL;DR: A number of derivatives of the ketohexose d -psicose have been synthesized, comprising examples of acetals, esters, ethers, and glycosides as discussed by the authors.
7 citations
TL;DR: In this article, the relative stability of different conformers of fructose in the gas phase, albeit somewhat approximately, can be obtained in terms of the collective effect of (i) the sum of the energies of all the hydrogen bonds in a given conformer, (ii) the strain energy of a bare fructose ring, and (iii) the anomeric stabilization (endo + exo) energies.
Abstract: Despite many experimental and theoretical investigations, a quantitative explanation of the factors governing the stability of sugars is rather scarcely attempted in the literature. A quantitative understanding of such factors is important for correlating the stability of these molecules with their function. Recent experimental–theoretical studies report the global minimum structure of fructose and provide qualitative information about the predominant factors that determine the overall stability. In the present work, we quantitatively show that the relative stability of different conformers of fructose in the gas phase, albeit somewhat approximately, can be obtained in terms of the collective effect of (i) the sum of the energies of all the hydrogen bonds in a given conformer, (ii) the strain energy of a bare fructose ring, and (iii) the sum of anomeric stabilization (endo + exo) energies. The combined effect of these three factors is indeed useful for explaining the conformational landscape of fructose. The calculated relative stability of fructose is in good agreement with the one obtained from the relative energies of these sugar molecules. The large energetic gap between pyranose and furanose conformers is also well-explained. It is concluded that the small ring strain, the sufficiently large sum of the energies of the intramolecular hydrogen bonds and the higher stabilization due to anomeric interactions in β-fructo-pyranose make it a conformationally locked predominant structure in the gas phase.
7 citations
TL;DR: In this article, the conformational space of D and L, deoxy and nondeoxy, 5thio-pyranoses with biological properties as enzymatic inhibitors was explored using MM and B3LYP/6-31+G* methods in gas phase and solution.
7 citations
TL;DR: The molecular mass, as well as the structures of both the saccharide and acylamide side chain involved in related substances, can be determined by applying the results obtained.
Abstract: Fragmentation mechanisms of electron ionization (EI) mass spectrometry of the title compounds have been elucidated by high-resolution (HR) mass spectrometric measurements of the elemental composition and measurements of the metastable transitions (B2/E, CID). The experimental results were interpreted with the help of Mass Frontier 3.0 software, which aided the elucidation of fragmentation mechanisms and helped to deduce structures of the ions formed. Characteristic under the conditions of EI-MS measurement was the production of protonated adducts. Three distinct pathways observed include the formation of oxonium type ions, the conjugated transfer of electrons in the pyranose ring, and cleavage of the acylamide side chains. By applying the results obtained, the molecular mass, as well as the structures of both the saccharide and acylamide side chain involved in related substances, can be determined. Copyright © 2003 John Wiley & Sons, Ltd.
7 citations
TL;DR: In this paper, 3-O-benzyl-D -allose with acetaldehyde forms a complex mixture from which potentially useful mono- and di-O -ethylidene derivatives were isolated and identified.
7 citations