Conformations of the d-glucarolactones and d-glucaric acid in solution

Derek Horton, Zbigniew Wałaszek

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

Abstract

The conformations of d-glucaric acid (1), d-glucaro-1,4-lactone (2), d-glucaro-6,3-lactone (3), and d-glucaro-1,4:6,3-dilactone (4) in solution were investigated by 1H-n.m.r. and 13C-p.F.t., n.m.r. spectroscopy. The solvents used were deuterium oxide, methanol-d4, and dimethyl sulfoxide-d6, and praseodymium chloride was employed as a lanthanide shift-reagent. For 2, it was found that the conformational equilibrium 3E(d) {A figure is presented} E3(d) exists in solution, and that the OH-5 group tends to occupy the position over the lactone ring in the favored E3(d),gg conformation. The n.m.r. data for 3 indicated that the conformational equilibrium is shifted in favor of the 4E(d) {A figure is presented} E4(d),gt conformation in solution. The dienvelope conformation 3E:E4(d) was found to be the favored conformation of 4. For 1, a conformational equilibrium between one planar, zigzag form and two sickle forms was indicated by the n.m.r. data observed. 13C-N.m.r. spectroscopy proved to be a convenient method for monitoring the lactonization of 1, and the hydrolysis of its lactones. Lactones other than 2-4 were not found in solutions prepared from 1-4, either during their mutarotation or after equilibration at 30°.

Original languageEnglish (US)
Pages (from-to)95-109
Number of pages15
JournalCarbohydrate Research
Volume105
Issue number1
DOIs
StatePublished - Jul 1 1982
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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