Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?
We have shown for the first time that taxadiene (3) can be epoxidised in a regio- and diastereoselective manner to provide taxadiene-4(5)-epoxide (12) as a single diastereoisomer, and that this epoxide can be rearranged to give taxa-4(20),11(12)-dien-5α-ol (4). Furthermore, the epoxide 12 rearranges...
| Main Authors: | Barton, Naomi A., Marsh, Benjamin J., Lewis, William, Narraidoo, Nathalie, Seymour, Graham B., Fray, Rupert George, Hayes, Christopher J. |
|---|---|
| Format: | Article |
| Published: |
Royal Society of Chemistry
2016
|
| Online Access: | https://eprints.nottingham.ac.uk/37455/ |
Similar Items
Investigation of Taxol biosynthetic genes for the production of novel taxanes in heterologous plant systems
by: Narraidoo, Nathalie
Published: (2011)
by: Narraidoo, Nathalie
Published: (2011)
Computational analysis of the taxadiene synthase reaction pathway
by: Amory, Ross
Published: (2025)
by: Amory, Ross
Published: (2025)
Synthetic chemistry and synthetic biology approaches to low oxidation state taxanes
by: Marsh, Benjamin J.
Published: (2017)
by: Marsh, Benjamin J.
Published: (2017)
Cloning enzymes of the taxol pathway and their expression in transgenic tomato
by: Alzahrani, Fatima
Published: (2016)
by: Alzahrani, Fatima
Published: (2016)
Investigation into the biotechnological applications of Pantoea agglomerans for the production of high value terpenoids such as taxadiene
by: Williamson, J J
Published: (2017)
by: Williamson, J J
Published: (2017)
Studies towards low oxidation state taxanes
by: Sadia, Reema
Published: (2022)
by: Sadia, Reema
Published: (2022)
Chemotherapeutic Agents: Taxol and Vincristine Isolated from Endophytic Fungi
by: Makky, Essam A., et al.
Published: (2015)
by: Makky, Essam A., et al.
Published: (2015)
Reconstruction of Curcuma aeruginosa secondary metabolite
biosynthetic pathway using omics data
by: Nurul-Syafika Mohamad-Fauzi,, et al.
Published: (2018)
by: Nurul-Syafika Mohamad-Fauzi,, et al.
Published: (2018)
Reconstruction of the transcriptional regulatory network in Arabidopsis thaliana aliphatic glucosinolate biosynthetic pathway
by: Khalidah-Syahirah Ashari,, et al.
Published: (2018)
by: Khalidah-Syahirah Ashari,, et al.
Published: (2018)
Flavor and aroma compounds of some exotic tropical fruits and berries: biosynthetic pathways and metabolism
by: Lasekan, Olusegun Ola
Published: (2016)
by: Lasekan, Olusegun Ola
Published: (2016)
Bevacizumab in combination with taxanes for the first-line treatment of metastatic breast cancer
by: Chan, Arlene, et al.
Published: (2010)
by: Chan, Arlene, et al.
Published: (2010)
Preoperative taxane-based chemotherapy in a standardized protocol for locally advanced breast cancer
by: Chan, Arlene, et al.
Published: (2012)
by: Chan, Arlene, et al.
Published: (2012)
Elucidation of Pigment Biosynthetic Pathways – Towards Integration of Metabolomics, Metabolic Flux Analysis, and Metabolic Engineering
by: Kamarudin, Kamarul Rahim, et al.
Published: (2012)
by: Kamarudin, Kamarul Rahim, et al.
Published: (2012)
Towards phenotypic characterisation of two potential food grade pigment producing microbes from New Zealand environment and elucidation of pigment biosynthetic pathways
by: Kamarudin, Kamarul Rahim, et al.
Published: (2010)
by: Kamarudin, Kamarul Rahim, et al.
Published: (2010)
Isolation and characterisation of carotenoid and genes involved in the carotenoid biosynthetic pathway from ipomoea leaves / Hue Seow Mun
by: Hue, Seow Mun
Published: (2012)
by: Hue, Seow Mun
Published: (2012)
Molecular Cloning And Characterization Of Cdna Encoding For Enzymes In The Carotenoid Biosynthetic Pathway Of Oil Palm (Elaeis Guineensis Jacq.)
by: Abd Rasid, Omar
Published: (2008)
by: Abd Rasid, Omar
Published: (2008)
Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions
by: Saska, J., et al.
Published: (2016)
by: Saska, J., et al.
Published: (2016)
N6-Methyladenosine Inhibits Local Ribonucleolytic
Cleavage to Stabilize mRNAs in Arabidopsis
by: Fray, Rupert G
Published: (2018)
by: Fray, Rupert G
Published: (2018)
Minimum Information about a Biosynthetic Gene cluster
by: Medema, M., et al.
Published: (2015)
by: Medema, M., et al.
Published: (2015)
Comparative genomics of cell wall remodelling
genes in fleshy fruit species and the control of fruit
softening in tomato
by: Samsulrizal, Nurul Hidayah, et al.
Published: (2017)
by: Samsulrizal, Nurul Hidayah, et al.
Published: (2017)
Mitochondrial phosphoenolpyruvate carboxykinase (PEPCK-M) and serine biosynthetic pathway genes are co-ordinately increased during anabolic agent-induced skeletal muscle growth
by: Brown, D.M., et al.
Published: (2016)
by: Brown, D.M., et al.
Published: (2016)
Mitochondrial phosphoenolpyruvate carboxykinase (PEPCK-M) and serine biosynthetic pathway genes are co-ordinately increased during anabolic agent-induced skeletal muscle growth
by: Brown, David M., et al.
Published: (2016)
by: Brown, David M., et al.
Published: (2016)
Allocate carbon for a reason: Priorities are reflected in the 13C/12C ratios of plant lipids synthesized via three independent biosynthetic pathways
by: Zhou, Youping, et al.
Published: (2015)
by: Zhou, Youping, et al.
Published: (2015)
Expansion and conservation of biosynthetic gene clusters in pathogenic Pyrenophora spp.
by: Moolhuijzen, Paula, et al.
Published: (2020)
by: Moolhuijzen, Paula, et al.
Published: (2020)
Tgf-β stimulated glycosaminoglycan (GAG) biosynthetic gene expression in vascular smooth muscle cells
by: Rostam, Muhamad Ashraf, et al.
Published: (2013)
by: Rostam, Muhamad Ashraf, et al.
Published: (2013)
Synthesis of epoxidized palm oil-based trimethylolpropane ester by in situ epoxidation method
by: Naidir, Ferra, et al.
Published: (2012)
by: Naidir, Ferra, et al.
Published: (2012)
Porous amphiphilic biogel from a facile chemo-biosynthetic route
by: Syed Mohamed, Syed Mohammad Daniel, et al.
Published: (2020)
by: Syed Mohamed, Syed Mohammad Daniel, et al.
Published: (2020)
Omniflow – A Biosynthetic Vascular Prosthesis : Current Evidence for use in Haemodialysis
by: Howell, S, et al.
Published: (2012)
by: Howell, S, et al.
Published: (2012)
The sound of silence: Activating silent biosynthetic gene clusters in marine microorganisms
by: Reen, F., et al.
Published: (2015)
by: Reen, F., et al.
Published: (2015)
Recent advances in catalytic and non-catalytic epoxidation of terpenes: a pathway to bio-based polymers from waste biomass
by: Gunam Resul, Mohamad Faiz Mukhtar, et al.
Published: (2023)
by: Gunam Resul, Mohamad Faiz Mukhtar, et al.
Published: (2023)
Inhibition of neuronal nitric oxide synthase expression and prevention of mitochondrial dysfunction at spinal ventral horn after c7 spinal root avulsion in rats with taxol
by: Sze Kiat, Sim
Published: (2014)
by: Sze Kiat, Sim
Published: (2014)
Method for epoxidation of plant oils.
by: Abdul Rahman, Mohd Basyaruddin, et al.
Published: (2009)
by: Abdul Rahman, Mohd Basyaruddin, et al.
Published: (2009)
Stromule formation is dependent upon plastid size, plastid differentiation status and the density of plastids within the cell
by: Waters, Mark, et al.
Published: (2004)
by: Waters, Mark, et al.
Published: (2004)
Actinophytocola sp. K4-08: rare actinomycete with potential biosynthetic capability
by: Mohd Zin, Nur Huda, et al.
Published: (2018)
by: Mohd Zin, Nur Huda, et al.
Published: (2018)
Characterization of the Saxitoxin Biosynthetic Starting Gene, sxta in the Toxic Dinoflagellate Alexandrium tamiyavanichii
by: Kieng, Soon Hii, et al.
Published: (2012)
by: Kieng, Soon Hii, et al.
Published: (2012)
Biosynthetic production of human growth hormone gene in methylotrophic yeast, Pichia pastoris
by: Loh, Danley, et al.
Published: (2004)
by: Loh, Danley, et al.
Published: (2004)
Expression analysis of fatty acid biosynthetic pathway genes during interactions of oil palm (Elaeis guineensis Jacq.) with the pathogenic Ganoderma boninense and symbiotic Trichoderma harzianum fungal organisms
by: Alizadeh, Fahimeh, et al.
Published: (2014)
by: Alizadeh, Fahimeh, et al.
Published: (2014)
Identification of regulatory motif for enhancing expression of oil palm fatty acid biosynthetic genes
by: Abu Hanifiah, Farah Hanan, et al.
Published: (2017)
by: Abu Hanifiah, Farah Hanan, et al.
Published: (2017)
Epoxidation and hydroxylation of liquid natural rubber
by: Nur Hanis Adila Azhar,, et al.
Published: (2017)
by: Nur Hanis Adila Azhar,, et al.
Published: (2017)
Demonstration that CobG, the monooxygenase associated with the ring contraction process of the aerobic cobalamin (vitamin B12) biosynthetic pathway, contains an Fe-S center and a mononuclear non-heme iron center
by: Schroeder, S., et al.
Published: (2009)
by: Schroeder, S., et al.
Published: (2009)
Similar Items
-
Investigation of Taxol biosynthetic genes for the production of novel taxanes in heterologous plant systems
by: Narraidoo, Nathalie
Published: (2011) -
Computational analysis of the taxadiene synthase reaction pathway
by: Amory, Ross
Published: (2025) -
Synthetic chemistry and synthetic biology approaches to low oxidation state taxanes
by: Marsh, Benjamin J.
Published: (2017) -
Cloning enzymes of the taxol pathway and their expression in transgenic tomato
by: Alzahrani, Fatima
Published: (2016) -
Investigation into the biotechnological applications of Pantoea agglomerans for the production of high value terpenoids such as taxadiene
by: Williamson, J J
Published: (2017)