Enzymic Oxidations of Ent-Kaurene and Ent-Kaurenol in Gibberellic Acid Biosynthesis: Stereochemistry and Isotope Effects

The mixed function oxidase (MFO) catalyzed C19 hydroxylations of ent-kaur-16-ene (1) and of ent-kaur-16-en-19-ol (2) precede a complex cascade of enzyme catalyzed reactions leading to the plant growth regulator gibberellic acid. The stereochemistry and deuterium isotope effects (k(,H)/k(,D)) of these two oxidations were studied using stereospecifically labelled derivatives of 1 and 2 and microsomal enzyme extracts of Marah macrocarpus (wild cucumber) as the MFO source.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Sherwin, Paul Frederick

• Chemistry, Organic

Identifier

(UMI)AAI8302985

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70206