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University of Manchester

1. Howard, Daniel. New Biocatalysts for Synthetically Useful Metabolites from Available Phenols.

Degree: 2019, University of Manchester

Toluene dioxygenase (TDO) is a Rieske type non-haem enzyme found within the soil bacteria, Pseudomonas putida (P. putida) and is responsible for catalysing the enantioselective cis-dihydroxylation of aromatic substrates. This remarkable trait of the TDO enzyme has enabled its application in the preparation of over 400 novel cis-diol bioproducts using whole cell biocatalysis. Recently, a new and synthetically useful bioproduct, (4S,5S)-4,5-dihydroxy-3-iodocyclohex-2-en-1-one, has been identified from the TDO catalysed biotransformation of 3-iodophenol. The purpose of this project was to demonstrate the synthetic application of this new bioproduct in the synthesis of natural product analogues, which possess anti-proliferative activity against different cancer cell lines. This was achieved by developing methodology towards a key enone building block, which was successfully applied in the synthesis of an analogue of the natural product incarviditone. Furthermore, a robust computational docking model was developed using the Goldâ„¢ software, which showed significant correlation between the predicted docking outcome and the experimentally observed results for a series of monocyclic substrates. The docking model was also used to rationalise the major and minor binding modes of the 3-iodophenol substrate in the TDO enzyme active site. The project also sought to develop an alternative synthetic methodology using butan-1,2-diacetal (BDA) protected (-)-quinic acid, which would provide the same stereochemical outcome as the newly discovered bioproduct. This was achieved despite considerable synthetic challenges encountered when trying to control the diastereoselectivity of a key conjugate addition reaction. The antipodal compounds of the natural product analogues obtained using the 3-iodophenol bioproduct and BDA protected (-)-quinic acid were also synthesised using acetonide protected (-)-quinic acid. By reacting the enantiomers of a key hydroxyenone intermediate obtained using the two pathways, a novel heterodimerisation was reported to afford an analogue of the natural product, incarvilleatone. Finally, all the biological activities of the synthesised natural product analogues were evaluated using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay: the results showed significant differences between the enantiomers of the incarviditone natural product analogues. Advisors/Committee Members: QUAYLE, PETER P, Whitehead, Roger, Quayle, Peter.

Subjects/Keywords: TDO; Dioxygenase; Toluene Dioxygenase; Quinic Acid; Incarvilleatone; Incarviditone; Biocatalysis; Iodo keto cis-diol; Iodo diol; P putida; Pseudomonas putida; P. putida UV4; COTC; Pseudohygrophorones

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Howard, D. (2019). New Biocatalysts for Synthetically Useful Metabolites from Available Phenols. (Doctoral Dissertation). University of Manchester. Retrieved from http://www.manchester.ac.uk/escholar/uk-ac-man-scw:318017

Chicago Manual of Style (16th Edition):

Howard, Daniel. “New Biocatalysts for Synthetically Useful Metabolites from Available Phenols.” 2019. Doctoral Dissertation, University of Manchester. Accessed July 07, 2020. http://www.manchester.ac.uk/escholar/uk-ac-man-scw:318017.

MLA Handbook (7th Edition):

Howard, Daniel. “New Biocatalysts for Synthetically Useful Metabolites from Available Phenols.” 2019. Web. 07 Jul 2020.

Vancouver:

Howard D. New Biocatalysts for Synthetically Useful Metabolites from Available Phenols. [Internet] [Doctoral dissertation]. University of Manchester; 2019. [cited 2020 Jul 07]. Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:318017.

Council of Science Editors:

Howard D. New Biocatalysts for Synthetically Useful Metabolites from Available Phenols. [Doctoral Dissertation]. University of Manchester; 2019. Available from: http://www.manchester.ac.uk/escholar/uk-ac-man-scw:318017

2. Howard, Daniel. New biocatalysts for synthetically useful metabolites from available phenols.

Degree: PhD, 2018, University of Manchester

Toluene dioxygenase (TDO) is a Rieske type non-haem enzyme found within the soil bacteria, Pseudomonas putida (P. putida) and is responsible for catalysing the enantioselective cis-dihydroxylation of aromatic substrates. This remarkable trait of the TDO enzyme has enabled its application in the preparation of over 400 novel cis-diol bioproducts using whole cell biocatalysis. Recently, a new and synthetically useful bioproduct, (4S,5S)-4,5-dihydroxy-3-iodocyclohex-2-en-1-one, has been identified from the TDO catalysed biotransformation of 3-iodophenol. The purpose of this project was to demonstrate the synthetic application of this new bioproduct in the synthesis of natural product analogues, which possess anti-proliferative activity against different cancer cell lines. This was achieved by developing methodology towards a key enone building block, which was successfully applied in the synthesis of an analogue of the natural product incarviditone. Furthermore, a robust computational docking model was developed using the Goldâ„¢ software, which showed significant correlation between the predicted docking outcome and the experimentally observed results for a series of monocyclic substrates. The docking model was also used to rationalise the major and minor binding modes of the 3-iodophenol substrate in the TDO enzyme active site. The project also sought to develop an alternative synthetic methodology using butan-1,2-diacetal (BDA) protected (-)-quinic acid, which would provide the same stereochemical outcome as the newly discovered bioproduct. This was achieved despite considerable synthetic challenges encountered when trying to control the diastereoselectivity of a key conjugate addition reaction. The antipodal compounds of the natural product analogues obtained using the 3-iodophenol bioproduct and BDA protected (-)-quinic acid were also synthesised using acetonide protected (-)-quinic acid. By reacting the enantiomers of a key hydroxyenone intermediate obtained using the two pathways, a novel heterodimerisation was reported to afford an analogue of the natural product, incarvilleatone. Finally, all the biological activities of the synthesised natural product analogues were evaluated using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay: the results showed significant differences between the enantiomers of the incarviditone natural product analogues.

Subjects/Keywords: 540; P putida; Pseudohygrophorones; COTC; P. putida UV4; Pseudomonas putida; Iodo keto cis-diol; Iodo diol; Incarviditone; Incarvilleatone; Quinic Acid; Toluene Dioxygenase; Dioxygenase; TDO; Biocatalysis

…respectively (Scheme 17).49, 50 Scheme 17: The bromo 63 and iodo cis-diol 64 precursors to… …e.e.) iodo keto cis-diol 117 (see Scheme 21) using P. putida UV4. These… …cis-diol 117 product and iodo catechol 113 side-product. The iodo keto cis-diol 117 is… …Iodo keto cis-diol 117 exhibited a t1/2 for aromatisation of 10 hours in 5 M HClO4 at 25 °C… …RT, 66 %. Conclusively, their research shows the potential of iodo keto cis-diol 117 by… 

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Howard, D. (2018). New biocatalysts for synthetically useful metabolites from available phenols. (Doctoral Dissertation). University of Manchester. Retrieved from https://www.research.manchester.ac.uk/portal/en/theses/new-biocatalysts-for-synthetically-useful-metabolites-from-available-phenols(3b656275-726e-4843-9b31-2bc4e57c64dc).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.771372

Chicago Manual of Style (16th Edition):

Howard, Daniel. “New biocatalysts for synthetically useful metabolites from available phenols.” 2018. Doctoral Dissertation, University of Manchester. Accessed July 07, 2020. https://www.research.manchester.ac.uk/portal/en/theses/new-biocatalysts-for-synthetically-useful-metabolites-from-available-phenols(3b656275-726e-4843-9b31-2bc4e57c64dc).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.771372.

MLA Handbook (7th Edition):

Howard, Daniel. “New biocatalysts for synthetically useful metabolites from available phenols.” 2018. Web. 07 Jul 2020.

Vancouver:

Howard D. New biocatalysts for synthetically useful metabolites from available phenols. [Internet] [Doctoral dissertation]. University of Manchester; 2018. [cited 2020 Jul 07]. Available from: https://www.research.manchester.ac.uk/portal/en/theses/new-biocatalysts-for-synthetically-useful-metabolites-from-available-phenols(3b656275-726e-4843-9b31-2bc4e57c64dc).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.771372.

Council of Science Editors:

Howard D. New biocatalysts for synthetically useful metabolites from available phenols. [Doctoral Dissertation]. University of Manchester; 2018. Available from: https://www.research.manchester.ac.uk/portal/en/theses/new-biocatalysts-for-synthetically-useful-metabolites-from-available-phenols(3b656275-726e-4843-9b31-2bc4e57c64dc).html ; https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.771372


University of Southern California

3. Pullanikat, Prasanna. Preparation of novel ligands for rhodium (II) and palladium (II) catalysts and application in the synthesis of palmerolide A and conversion of biomass into formic acid.

Degree: PhD, Chemistry, 2012, University of Southern California

This dissertation focuses on the studies toward total synthesis of palmerolide A, preparation of ligands for rhodium catalyzed C-H activation reaction. Preparation of NHC-Pd (II) catalyst and the application in the conversion of biomass into formic acid.; In chapter 1, different schemes were discussed in the synthesis of subunits of palmerolide A.; In chapter 2, ligands were prepared and used in Rhodium (II) catalyzed C-H desymmetrization reactions. Preparation of intermediates were discussed in the synthesis of kainic acid and allokainic acid.; In chapter 3, Preparation of NHC-Pd catalyst and its application in the conversion of biomass into formic acid was discussed. Oxidative degradation of biomass in presence of cationic palladium was also discussed.; In chapter 4, oxidative degradation of carbohydrates under mild conditions in presence of hydrogen peroxide and ammonium hydroxide was discussed. Advisors/Committee Members: Jung, Kyung Woon (Committee Chair), Prakash, G.K. Surya (Committee Member), Neamati, Nouri (Committee Member).

Subjects/Keywords: palmerolide A; (E)-ethyl octa-2,7-dienoate; (R,E)-ethyl 7,8-dihydroxyoct-2-enoate; (R,E)-ethyl 8-((tert-butyldiphenylsilyl)oxy)-7-hydroxyoct-2-enoate; (R,E)-ethyl 8-((tert-butyldiphenylsilyl)oxy)-7-(methoxymethoxy) oct-2-enoate; (R,E)-ethyl 8-hydroxy-7-(methoxymethoxy)oct-2-enoate; (R,E)-ethyl 7-(methoxymethoxy)-8-((methylsulfonyl)oxy)oct-2-enoate; (R,E)-ethyl 8-iodo-7-(methoxymethoxy)oct-2-enoate; (4S,5S)-dimethyl 2,2-dimethyl-1,3-dioxolane -4,5-dicarboxylate; ((4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)dimethanol; ((4R,5R)-5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol; ((4R,5R)-5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl4-methylbenzene sulfonate; (2R,3R)-2,3-dihydroxy-4-((4-methoxybenzyl)oxy)butyl-4-methylbenzenesulfonate; (R)-2-((4-methoxybenzyl)oxy)-1-((R)-oxiran-2-yl)ethanol; (R)-2-((R)-2-((4-methoxybenzyl)oxy)-1-(methoxy methoxy)ethyl) oxirane; (2R,3R)-1-((4-methoxy benzyl)oxy)-2-(methoxymethoxy)hex-5-yn-3-ol; (4R,5S)-4-(iodomethyl)-5-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane; (R)-1-((4-methoxybenzyl)oxy)but-3-en-2-ol; (R,E)-(8-ethoxy-2-hydroxy-8-oxooct-6-en-1- yl)triphenylphosphonium iodide; hex-5-en-1-yl benzoate; (R)-5,6-dihydroxyhexyl benzoate; (R)-5-((tert-butyldimethylsilyl)oxy)-6-hydroxyhexyl benzoate; (R)-5-((tert-butyldimethylsilyl)oxy)6-oxohexylbenzoate; R, E)-5-((tert-butyldimethylsilyloxy)-7-iodohept-6-en-1-yl benzoate; methyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate; 2-(2-methyl-1,3-dioxolan-2-yl)ethanol; 2-(2-methyl-1,3-dioxolan-2-yl)acetaldehyde; (E)-ethyl 4-(2-methyl-1,3-dioxolan-2-yl)but-2-enoate; (E)-4-(2-methyl-1,3-dioxolan-2-yl)but-2-en-1-ol; ((2R,3R)-3-((2-methyl-1,3-dioxolan-2-yl)methyl)oxiran-2-yl)methanol; (2S,3R)-2-methyl-4-(2-methyl-1,3-dioxolan-2-yl)butane-1,3-diol; (4R,5S)-2-(4-methoxyphenyl)-5-methyl-4-((2-methyl-1,3-dioxolan-2-yl)methyl)-1,3-dioxane; (4R,5S)-2-(4-methoxyphenyl)-5-methyl-4-(2-methylallyl)-1,3-dioxane; (2R,3S)-3-methyl-1-(2-methyl-1,3-dioxolan-2-yl)pent-4-yn-2-ol and (4R,5S)-4-hydroxy-5-methylhept-6-yn-2-one; tert-butyldimethyl(((2R,3S)-3-methyl-1(2-methyl-1,3-dioxolan-2-yl)hex-4-yn-2-yl) oxy) silane; (E)-methyl 5-methylhexa-2,5-dienoate; (E)-5-methylhexa-2,5-dien-1-ol; ((2R,3R)-3-(2-methylallyl)oxiran-2-yl)methanol; (2S,3R)-2,5-dimethylhex-5-ene-1,3-diol; (4R,5S)-2-(4-methoxyphenyl)-5-methyl-4-(2-methylallyl)-1,3-dioxane; (4S,5R,E)-5-((4-methoxybenzyl)oxy)-2,4,7-trimethylocta-2,7-dienal; (2R,3R)-hept-6-yne-1,2,3-triol; methyl 2-((4S,4'R,5R)-2,2,2',2'-tetramethyl [4,4'-bi(1,3- dioxolan)]-5-yl)acetate; 4-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-4 hydroxy-but-2-enoic acid methylester; 4-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-hydroxy-but-2-enoic acid methylester; (4S,E)-methyl 4-((tert-butyldiphenylsilyl)oxy)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate; (S,E)-4-((tert-butyldiphenylsilyl)oxy)-4-((R)-2,2-dimethyl-1,3-dioxo lan-4-yl)but-2-en-1-ol; (S,E)-4-((tert-butyldiphenylsilyl)oxy)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enal; 4-((4-methoxybenzyl)oxy)butan-1-ol; 1-((4-iodobutoxy)methyl)-4-methoxybenzene; 1-((4-iodobutoxy)methyl)-4-methoxybenzene; (5S,E)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)8-(4-((4-methoxybenzyl)oxy)butyl)-2,2,10,10,11,11-hexamethyl-3,3-diphenyl-4,9-dioxa-3,10-disiladodec-6-ene; (2R,3S,E)-3-((tert-butyldiphenylsilyl)oxy) 10-((4-methoxybenzyl) oxy)dec-4-ene-1,2,6-triol; (2R,3S,E)-3,6-bis((tert-butyldiphenylsilyl)oxy) 10-((4-methoxybenzyl) oxy)dec-4-ene-1,2-diol; (2R,3S,E)-3,6-bis((tert-butyldiphenylsilyl) oxy)-2-hydroxy-10-((4-methoxybenzyl)oxy)dec-4-en-1 yl benzoate; (2R,3S,E)-3,6-bis((tert-butyldiphenylsilyl)oxy)-10 ((4-methoxybenzyl)oxy)-2-((methylsulfonyl)oxy)dec-4-en-1-ylbenzoate; (8S,E)-5-(4-((4-methoxybenzyl)oxy)butyl)-2,2,11,11-tetramethyl-8-((S)-oxiran-2-yl)-3,3,10,10-tetra-phenyl-4,9-dioxa-3,10-disiladodec-6-ene; (4S,5R)-4-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-5-((phenyl sulfonyl)methyl)-1,3-dioxolane; diazoamide compounds; 1-[4,4-bis-(tert-butyl-dimethyl silanyloxymethyl)-2,2-dimethyloxazolidin-3-yl]2-diazo-ethanone; 1-[4,4-bis-(tert-butyl-dimethylsilanyloxymethyl)-2,2-dimethyloxazolidin-3-yl]-2-diazo-ethanone; 1-(4,4-bis(((tert-butyldimethylsilyl)oxy)methyl)- 2,2-dimethyloxazo- lidin-3-yl)-2-diazoethanone; 1-trifluoromethanesulfonylimidazolidin-2-one ligands; 1-[4,4-bis-(tertbutyldimethylsilanyloxy- methyl)2,2-dimethyl-oxazolidin-3-yl]2-diazo-butane-1,3-dione; 1-[3,3-bis-(tert-butyl-dimethylsilanyloxymethyl)-1-oxa-4- aza-spiro[4.5]dec-4-yl]-2-diazo-ethanone; 1-[3,3-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-oxa-4-aza-spiro[4.5]dec-4-yl]-2-diazobutane-1,3-dione; trans-1-benzylhexahydro-1H-indol-(3H)-one; N-cyclohexyl-2-diazo-N-phenyl 2-(phenylsulfonyl)acetamide NHC-Pd complex; oxidative degradation; biomass; carbohydrates; glycerol; ethylene glycol; glycolic acid

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Pullanikat, P. (2012). Preparation of novel ligands for rhodium (II) and palladium (II) catalysts and application in the synthesis of palmerolide A and conversion of biomass into formic acid. (Doctoral Dissertation). University of Southern California. Retrieved from http://digitallibrary.usc.edu/cdm/compoundobject/collection/p15799coll127/id/440514/rec/5201

Chicago Manual of Style (16th Edition):

Pullanikat, Prasanna. “Preparation of novel ligands for rhodium (II) and palladium (II) catalysts and application in the synthesis of palmerolide A and conversion of biomass into formic acid.” 2012. Doctoral Dissertation, University of Southern California. Accessed July 07, 2020. http://digitallibrary.usc.edu/cdm/compoundobject/collection/p15799coll127/id/440514/rec/5201.

MLA Handbook (7th Edition):

Pullanikat, Prasanna. “Preparation of novel ligands for rhodium (II) and palladium (II) catalysts and application in the synthesis of palmerolide A and conversion of biomass into formic acid.” 2012. Web. 07 Jul 2020.

Vancouver:

Pullanikat P. Preparation of novel ligands for rhodium (II) and palladium (II) catalysts and application in the synthesis of palmerolide A and conversion of biomass into formic acid. [Internet] [Doctoral dissertation]. University of Southern California; 2012. [cited 2020 Jul 07]. Available from: http://digitallibrary.usc.edu/cdm/compoundobject/collection/p15799coll127/id/440514/rec/5201.

Council of Science Editors:

Pullanikat P. Preparation of novel ligands for rhodium (II) and palladium (II) catalysts and application in the synthesis of palmerolide A and conversion of biomass into formic acid. [Doctoral Dissertation]. University of Southern California; 2012. Available from: http://digitallibrary.usc.edu/cdm/compoundobject/collection/p15799coll127/id/440514/rec/5201

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