Structures of d-threo-2,5-hexodiulose 1-phosphate and d-threo-2,5-hexodiulose 1,6-bisphosphate (5-keto-d-fructose mono- and bis-phosphate) in solution by 13C-N.M.R. spectroscopy

Loredana Butera, Sasha Englard, John S. Blanchard, Gad Avigad

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The mono- (2) and bis-phosphate (3) derivatives of d-threo-2,5-hexodiulose (1) (5-keto-d-fructose) were synthesized enzymically and purified by anion-exchange chromatography. The proportions, sizes of ring, and anomeric configurations were determined by F.t. 31P- and 13C-n.m.r. spectroscopy. Compound 2 was found to exist preponderantly (70-78%) in the β-pyranose form with the remainder existing in the 2R,5R-furanose form. Compound 3 assumes two different furanose forms in solution, one (77-84%) being the 2R,5R-furanose form and the other the 2S,5R-furanose form.

Original languageEnglish (US)
Pages (from-to)179-188
Number of pages10
JournalCarbohydrate Research
Issue number2
Publication statusPublished - May 1 1986


ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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