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Silicate complexes of sugars in aqueous solution.

Joseph B Lambert1, Gang Lu, Stephanie R Singer

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA. jlambert@northwestern.edu

Journal of the American Chemical Society
|August 5, 2004
PubMed
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Certain sugars form soluble silicate complexes with silicic acid, but only specific furanose forms react. This selective reaction, involving the anomeric hydroxyl group, has implications for prebiotic chemistry.

Area of Science:

  • Carbohydrate Chemistry
  • Silicate Chemistry
  • Prebiotic Chemistry

Background:

  • Sugars can react with silicic acid to form soluble silicate complexes.
  • The structure of the sugar and its configuration are critical for complex formation.

Purpose of the Study:

  • To investigate the structural requirements for sugar-silicic acid complex formation.
  • To understand the selectivity of this reaction and its potential implications.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy, specifically (29)Si and (13)C NMR, was used to analyze the products.
  • Studied the reaction of various monosaccharides and disaccharides with basic silicic acid.

Main Results:

  • Only furanose forms of sugars reacted with silicic acid, forming 2/1 (sugar/silicic acid) chelates.

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  • Reaction requires the anomeric hydroxyl group to be cis to an adjacent hydroxyl group.
  • Specific sugars like ribose, xylose, and fructose formed complexes, while glucose and galactose did not.
  • Conclusions:

    • Sugar silicate complex formation is highly selective, depending on sugar structure and hydroxyl group configuration.
    • The reaction mechanism involves chelation via a five-membered diolato ring.
    • This selectivity may play a role in prebiotic chemical processes.