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

Research output: Contribution to journalArticle

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Abstract

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
Volume148
Issue number2
DOIs
StatePublished - May 1 1986

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Chromatography
Fructose
Nuclear magnetic resonance spectroscopy
Anions
Spectrum Analysis
Magnetic Resonance Spectroscopy
Phosphates
Spectroscopy
Derivatives
Carbon-13 Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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

In: Carbohydrate Research, Vol. 148, No. 2, 01.05.1986, p. 179-188.

Research output: Contribution to journalArticle

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