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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Two halodeoxy sucrose analogues.

A Linden1, C K Lee, A S Muhammad Sofian

  • 1Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland. alinden@oci.unizh.ch

Acta Crystallographica. Section C, Crystal Structure Communications
|November 14, 2001
PubMed
Summary
This summary is machine-generated.

Structural analysis of brominated sucrose derivatives reveals distinct conformations. While 4-bromo-4-deoxysucrose closely resembles sucrose, 1

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Area of Science:

  • Carbohydrate Chemistry
  • Crystallography
  • Structural Biology

Background:

  • Sucrose is a common disaccharide with a well-defined structure.
  • Modified sucrose analogues are synthesized to explore structure-activity relationships.
  • Understanding the conformational impact of halogenation is crucial for carbohydrate chemistry.

Purpose of the Study:

  • To determine the crystal structures of two halogenated sucrose derivatives.
  • To compare the conformational properties of these derivatives with sucrose and sucralose.
  • To investigate the role of intramolecular and intermolecular hydrogen bonding in these structures.

Main Methods:

  • Single-crystal X-ray diffraction at 160 K.
  • Analysis of molecular conformation and hydrogen bonding networks.
  • Determination of absolute configuration.

Main Results:

  • 4-bromo-4-deoxysucrose exhibits a structure similar to sucrose, including an intramolecular hydrogen bond.
  • 1',6'-dibromo-4-fluoro-4,1',6'-trideoxysucrose monohydrate shows significant conformational differences from sucrose and sucralose.
  • Neither derivative exhibits the same intramolecular hydrogen bonding pattern as sucrose.
  • Both compounds form extensive three-dimensional networks via intermolecular hydrogen bonds.

Conclusions:

  • Halogenation at specific positions can drastically alter sucrose derivative conformation.
  • Intramolecular hydrogen bonding plays a key role in stabilizing sucrose conformation.
  • Intermolecular hydrogen bonding dictates the solid-state packing of these halogenated sucrose analogues.