Model experiments in biosynthesis using phosphate esters

Miller, John A (1965) Model experiments in biosynthesis using phosphate esters. PhD thesis, University of Glasgow.

Abstract

The synthesis of a range of allyl- and 3,3-dialkylallyldiaryl phosphates has been achieved. Some of these esters, notably the polyisoprenoid phosphates, have been found to be extremely unstable, and to decompose spontaneously. All the allyl- and 3,3-dialkylallyldiaryl phosphates studied were found to eliminate diaryl phosphate readily, when attacked by different nucleophiles, and are therefore alkylating agents. The nucleophiles used included alkenes, the oxygen atom and anionoid ring-positions of phenols, and the sulphur atom of thiols and sulphides. The efficiency of these alkylations varied greatly from system to system, and was very sensitive to changes in solvent, and to changes in the stereochemistry of the reactants. The experiments with terpenoid phosphates, and those concerned with alkylation of phenols, are believed to have some chemical significance, as models for the biosynthesis of terpenes and phenolic isoprenoide.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Additional Information: Adviser: H CS Wood
• Keywords: Organic chemistry
• Date of Award: 1965
• Depositing User: Enlighten Team
• Unique ID: glathesis:1965-73810
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 14 Jun 2019 08:56
• Last Modified: 14 Jun 2019 08:56
• URI: https://theses.gla.ac.uk/id/eprint/73810