Deuterium labelling of ent-kaur-16-en-19-oic acid at carbon-6 and -7

[6α- 2H]-, [6β- 2H]-, [7α- 2H]-, [7β- 2H]-, [6,6- 2H 2]-, [7,7- 2H 2]- and [6β,7β- 2H 2] ent-Kaur-16-en-19-oic acids have been prepared from 7β-hydroxykaurenolide, a metabolite of the fungus, Gibberella fujikuroi. The chemical and stereochemical purity of the labelled acids have been determined by G...

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Published inPhytochemistry (Oxford) Vol. 29; no. 6; pp. 1823 - 1831
Main Authors Castellaro, Simon J., Dolan, Simon C., MacMillan, Jake, Willis, Christine L.
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier Ltd 1990
Elsevier
Subjects
biochemical pathways
Biological and medical sciences
biosynthesis
chemical structure
Cucurbita maxima
deuterium
Deuterium labelling
Fundamental and applied biological sciences. Psychology
Gibberella fujikuroi
gibberellin
kaura-6,16-dienoic acid
kaurenoic acid
kaurenolide
metabolism
Plant physiology and development
radiolabeling
stereochemistry
synthesis, stereospecificity
kaurenolide
kaura-6,16-dienoic acid
Deuterium labelling
kaurenoic acid
gibberellin
synthesis, stereospecificity
Deuterium
Stereospecificity
Radiolabelling
Chemical synthesis
Gibberellins
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Summary:[6α- 2H]-, [6β- 2H]-, [7α- 2H]-, [7β- 2H]-, [6,6- 2H 2]-, [7,7- 2H 2]- and [6β,7β- 2H 2] ent-Kaur-16-en-19-oic acids have been prepared from 7β-hydroxykaurenolide, a metabolite of the fungus, Gibberella fujikuroi. The chemical and stereochemical purity of the labelled acids have been determined by GC-MS and by 1H and 2H NMR spectroscopy. ent-[7- 2H]Kaura-6,16-dienoic acid and methyl ent-[6- 2H]-17-hydroxykauran-6-en-19-oate have also been prepared. Their 1H NMR spectra show that a previous assignment of the 6- and 7-hydrogen signals in ent-kaura- 6,16-dienoic acid should be reversed.
ISSN:0031-9422
1873-3700
DOI:10.1016/0031-9422(90)85023-9