Formation of 4-deoxy-glycero-hexo-2,3-diulo-furanose from microthecin

Abstract

4-Deoxy-glycero-hexo-2,3-diulose was formed from microthecin [2-hydroxy-2-(hydroxymethyl)-2H-pyran-3(6H)-one] in neutral water solutions by a Michael addition. The compound was determined by NMR spectroscopy, MS and polarimetry to be a racemic mixture of D-and L-forms and existing mainly as two furanosidic C-2 epimers in equilibrium with microthecin. GC-MS analysis showed that 4-deoxy-glycero-hexo-2,3-diulose and microthecin were present in extracts of the red alga Gracilariopsis lemaneiformis. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

Keywords

1,5-anhydro-D-fructose; microthecin; 2,3-diulose; Gracilariopsis lemaneiformis; gracilariales

Published in

Carbohydrate Research
1998, Volume: 306, number: 1-2, pages: 171-175

SLU Authors

• Broberg, Anders

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

• Kenne, Lennart

  • Department of Molecular Sciences, Swedish University of Agricultural Sciences
    

UKÄ Subject classification

Organic Chemistry


Publication identifier

DOI: https://doi.org/10.1016/S0008-6215(97)10045-3

Permanent link to this page (URI)

https://res.slu.se/id/publ/87623