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Synthesis and bioactivity of the gibberellin, 18 hydroxy-GA 1 (GA 132 )

Morrison (previously Beck), Ellen; Chandler, Peter; Thomson, Regan; Mander, Lewis

Description

As part of a study to confirm putative structural assignments to new gibberellins and to furnish sufficient quantities for biological investigations, a twenty step synthesis of 18-hydroxy GA1 from gibberellic acid (GA3) is described, allowing the confirmation of structure for a new gibberellin, GA132, that occurs in developing grains of barley (Hordeum vulgare). The early part of the sequence involved cleavage of the C(3)-C(4) bond in the A-ring of a 3-oxo intermediate. The ring was then...[Show more]

dc.contributor.authorMorrison (previously Beck), Ellen
dc.contributor.authorChandler, Peter
dc.contributor.authorThomson, Regan
dc.contributor.authorMander, Lewis
dc.date.accessioned2015-12-10T22:15:43Z
dc.identifier.issn1477-0520
dc.identifier.urihttp://hdl.handle.net/1885/50817
dc.description.abstractAs part of a study to confirm putative structural assignments to new gibberellins and to furnish sufficient quantities for biological investigations, a twenty step synthesis of 18-hydroxy GA1 from gibberellic acid (GA3) is described, allowing the confirmation of structure for a new gibberellin, GA132, that occurs in developing grains of barley (Hordeum vulgare). The early part of the sequence involved cleavage of the C(3)-C(4) bond in the A-ring of a 3-oxo intermediate. The ring was then reformed as part of a "domino" process involving the conjugate addition of alkoxide to an α-methylene lactone moiety followed by an intramolecular aldol reaction. The bioactivities of the new GA, and its 18-hydroxy-GA 4 relative, have been confirmed in dwarf barley growth and α-amylase induction assays.
dc.publisherRoyal Society of Chemistry
dc.sourceOrganic and Biomolecular Chemistry
dc.subjectKeywords: Amylase induction; Barley; Gibberellin; Intramolecular aldol reaction; Bioactivity; Biosynthesis; Hydroxylation; Molecular structure; Reaction kinetics; Hormones; 18 hydroxygibberellic acid 1; 18-hydroxygibberellic acid 1; amylase; gibberellic acid; gibbe
dc.titleSynthesis and bioactivity of the gibberellin, 18 hydroxy-GA 1 (GA 132 )
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume6
dc.date.issued2008
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.absfor060705 - Plant Physiology
local.identifier.ariespublicationu4005981xPUB211
local.type.statusPublished Version
local.contributor.affiliationMorrison (previously Beck), Ellen, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationChandler, Peter, CSIRO
local.contributor.affiliationThomson, Regan, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMander, Lewis, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue8
local.bibliographicCitation.startpage1416
local.bibliographicCitation.lastpage1424
local.identifier.doi10.1039/b800728d
dc.date.updated2015-12-09T08:20:07Z
local.identifier.scopusID2-s2.0-41549136496
local.identifier.thomsonID000254634200013
CollectionsANU Research Publications

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