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Title: Chemoenzymatic approaches to monoterpenoids
Author: Yoosuf Aly, Fathima
ISNI:       0000 0004 5355 1359
Awarding Body: Cardiff University
Current Institution: Cardiff University
Date of Award: 2014
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Terpenoids are the largest and structurally most diverse family of natural product. α-pinene, a monoterpene found in turpentine, is a precursor to several high-value monooxygenated terpenoids such as verbenone. It is produced naturally through the Mg2+ -dependent transformation of geranyl diphosphate (GDP) catalysed by (+)-α-pinene synthase (APS). Heterologous expression, purification and characterization of recombinant (+)-α-pinene synthase were performed. Several expression conditions and many purification methods were tried in order to get optimum results. After optimisation of His tagged α-pinene synthase (HAPS), chemoenzymatic synthesis of a simple two-step, one pot asymmetric synthesis from GDP of (+)-verbenone, an oxidation product of the monoterpene (+)-α-pinene, that is used to control attacks of pine trees by bark beetles is described. This method generates (+)-verbenone from GDP in good yield and without the need to isolate the intermediate (+)-α-pinene. Then, synthesis of some chemically modified GDP analogues to obtain (+)-α-pinene analogues was performed. These engineered (+)-α-pinene analogues may display enhanced biological activities due to the potential improvement of their physical properties. Finally, site directed mutagenesis strategy was employed to HAPS to examine the potential catalytic role of several aromatic amino acids, in stabilizing the carbocationic intermediates generated in the active site of HAPS during the natural conversion of GDP to the monoterpene (+)-α-pinene.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry