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Fischer Projections

Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
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At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
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A Strategy for Sensitive, Large Scale Quantitative Metabolomics

Published on: May 27, 2014

Free fructose is conformationally locked.

Emilio J Cocinero1, Alberto Lesarri, Patricia Écija

  • 1Departamento de Química Física, Facultad de Ciencia y Tecnología, Universidad del País Vasco (UPV-EHU), Apartado 644, 48080 Bilbao, Spain. emiliojose.cocinero@ehu.es

Journal of the American Chemical Society
|January 26, 2013
PubMed
Summary

Free fructose exists in a stable beta-pyranose form, unlike its furanose structure in polysaccharides. This conformation is maintained by intramolecular hydrogen bonds and anomeric effects.

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Area of Science:

  • Physical chemistry
  • Molecular spectroscopy
  • Carbohydrate chemistry

Background:

  • Fructose is a key monosaccharide with diverse biological roles.
  • Understanding fructose's free-molecule structure is crucial for its biochemical function.
  • Previous studies suggested conformational flexibility, contrasting with observed structures in polysaccharides.

Purpose of the Study:

  • To determine the precise structure of isolated fructose molecules.
  • To investigate the conformational preferences of fructose in the gas phase.
  • To compare the gas-phase structure with its forms in biological contexts.

Main Methods:

  • Isolation of fructose using UV ultrafast laser vaporization.
  • High-resolution rotational spectroscopy using Fourier-transform microwave (FT-MW) spectroscopy.
  • Analysis of isotopic species (13C and D) to confirm structural assignments.

Main Results:

  • Fructose exists exclusively in a single, dominant beta-pyranose conformation in isolation.
  • This conformation features a (2)C(5) chair-like structure, stabilized by five intramolecular hydrogen bonds.
  • The observed structure contrasts sharply with the furanose form found in polysaccharides like sucrose.

Conclusions:

  • The free fructose molecule is conformationally locked, favoring a specific beta-pyranose structure.
  • Intramolecular hydrogen bonding and anomeric effects are key to its stability.
  • This finding provides critical insights into fructose's behavior at a molecular level, distinct from its polymeric forms.