The stereochemistry of the hydrogen atoms at C-5′of abscisic acid

R. D. Willows*, B. V. Milborrow

*Corresponding author for this work

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Slices of unripe avocado fruit placed in 2H2O (45 atom %) synthesized abscisic acid enriched 18.7% with 2H at C-5′. 500 MHz 1H NMR showed that the signal of the axial, 5′-pro-S H atom was decreased by 20%. The signal of the uncoupled, equatorial H atom was 9 Hz upfield owing to shielding from its geminal 2H partner, the reciprocal shielding was 8.9 Hz. The H+ added during cyclization, therefore, is at the C-5′-pro-S position of ABA. Unlabelled ABA leaked into the medium, the newly synthesized, 2H labelled ABA was retained in the tissue.

Original languageEnglish
Pages (from-to)2641-2642
Number of pages2
JournalPhytochemistry
Volume28
Issue number10
DOIs
Publication statusPublished - 1989
Externally publishedYes

Keywords

  • H shielding
  • abscisic acid
  • Avocado
  • biosynthesis
  • cyclization
  • NMR.

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