David O'Hagan

Summary

Affiliation: University of St Andrews
Country: UK

Publications

  1. doi request reprint Synthesis and structure of large difluoromethylene containing alicycles by ring closing metathesis (RCM)
    Maciej Skibiński
    EaStCHEM School of Chemistry and Biomedical Sciences Research Centre, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK
    Org Biomol Chem 11:8209-13. 2013
  2. ncbi request reprint Organofluorine chemistry: synthesis and conformation of vicinal fluoromethylene motifs
    David O'Hagan
    EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST, United Kingdom
    J Org Chem 77:3689-99. 2012
  3. doi request reprint [18F]-5-Fluoro-5-deoxyribose, an efficient peptide bioconjugation ligand for positron emission tomography (PET) imaging
    Xiang Guo Li
    University of St Andrews, School of Chemistry and Centre for Biomolecular Science, North Haugh, St Andrews, Fife KY16 9ST, UK
    Chem Commun (Camb) 48:5247-9. 2012
  4. ncbi request reprint Biochemistry: biosynthesis of an organofluorine molecule
    David O'Hagan
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Nature 416:279. 2002
  5. doi request reprint 3-fluoro-GABA enantiomers: exploring the conformation of GABA binding to GABAA receptors and GABA aminotransferase
    David O'Hagan
    School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK
    Future Med Chem 3:189-95. 2011
  6. doi request reprint Understanding organofluorine chemistry. An introduction to the C-F bond
    David O'Hagan
    School of Chemistry and Centre for Biomolecular Science, University of St Andrews, North Haugh, St Andrews, UK KY16 9ST
    Chem Soc Rev 37:308-19. 2008
  7. doi request reprint An enzymatic route to 5-deoxy-5-[18F]fluoro-D-ribose, a [18F]-fluorinated sugar for PET imaging
    Mayca Onega
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, UKKY16 9ST
    Chem Commun (Camb) 46:139-41. 2010
  8. pmc The fluorinase from Streptomyces cattleya is also a chlorinase
    Hai Deng
    School of Chemistry and Centre for Biomolecular Science, University of St Andrews, St Andrews, KY16 9ST, UK
    Angew Chem Int Ed Engl 45:759-62. 2006
  9. ncbi request reprint Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process
    Stephen Patterson
    School of Chemistry, Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Phytochemistry 61:323-9. 2002
  10. ncbi request reprint The identification of 5'-fluoro-5-deoxyinosine as a shunt product in cell free extracts of Streptomyces cattleya
    Steven L Cobb
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, St Andrews, Fife, UK
    Bioorg Chem 33:393-401. 2005

Collaborators

  • Hai Deng
  • John T G Hamilton
  • Luke Hunter
  • Tanja van Mourik
  • Xiang Guo Li
  • Robert J Young
  • Rebecca J M Goss
  • Yi Wang
  • Stephen Thompson
  • Zixin Deng
  • Peng Li
  • Christophe Plisson
  • Margit Winkler
  • Patrick S Covello
  • Alexandra M Z Slawin
  • Poh Wai Chia
  • Alastair J Durie
  • Christoph Schaffrath
  • Tomas Lebl
  • Andrew Nortcliffe
  • K K Jason Chan
  • Mayca Onega
  • Vincent A Brunet
  • Steven L Cobb
  • César A Urbina-Blanco
  • Maciej Skibiński
  • Peer Kirsch
  • Changjiang Dong
  • Nigel P Botting
  • Steven P Nolan
  • Chunhua Zhao
  • James H Naismith
  • Václav Jurčík
  • Guillaume G Launay
  • Stefano Bresciani
  • Daniel Farran
  • Pitak Nasomjai
  • Ryan P McGlinchey
  • David J Tozer
  • Michael J G Peach
  • Gildas Deniau
  • Natalie E J Gooseman
  • Cosimo D Cadicamo
  • Cormac D Murphy
  • James A Ross
  • James R Black
  • Stephen Patterson
  • Alexander G Ekstrom
  • Fouad K Habib
  • Davide Bello
  • David J A Wyllie
  • Hong Yu Ou
  • Matthew R Livesey
  • Daniela Riccardi
  • Sarah C Brennan
  • Andrew E Welch
  • Antony D Gee
  • Timothy A D Smith
  • Lutz F Schweiger
  • Juozas Domarkas
  • Darwin W Reed
  • Keith T Sillar
  • Jeremy J Lambert
  • Judith M Heygate
  • Fatima Chorki
  • Jon P Issberner
  • Lori An Etherington
  • Andrew R McEwan
  • David A Robinson
  • Fanglu Huang
  • Jonathan B Spencer
  • Abdelkrim Meddour
  • Jacques Courtieu
  • Mark Dorward

Detail Information

Publications50

  1. doi request reprint Synthesis and structure of large difluoromethylene containing alicycles by ring closing metathesis (RCM)
    Maciej Skibiński
    EaStCHEM School of Chemistry and Biomedical Sciences Research Centre, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK
    Org Biomol Chem 11:8209-13. 2013
    ..X-Ray structures revealed that the resultant rings have the CF2 groups located only at corner positions and that these groups dictated the overall macrocyclic ring conformations. ..
  2. ncbi request reprint Organofluorine chemistry: synthesis and conformation of vicinal fluoromethylene motifs
    David O'Hagan
    EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST, United Kingdom
    J Org Chem 77:3689-99. 2012
    ..These motifs obey almost predictable conformational behavior, and they emerge as candidates for inclusion in the design of performance organic molecules...
  3. doi request reprint [18F]-5-Fluoro-5-deoxyribose, an efficient peptide bioconjugation ligand for positron emission tomography (PET) imaging
    Xiang Guo Li
    University of St Andrews, School of Chemistry and Centre for Biomolecular Science, North Haugh, St Andrews, Fife KY16 9ST, UK
    Chem Commun (Camb) 48:5247-9. 2012
    ..18)F]-5-Fluoro-5-deoxyribose ([(18)F]-FDR) conjugates much more rapidly than [(18)F]-FDG under mild reaction conditions to peptides and offers new prospects for mild and rapid bioconjugation for fluorine-18 labelling in PET imaging...
  4. ncbi request reprint Biochemistry: biosynthesis of an organofluorine molecule
    David O'Hagan
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Nature 416:279. 2002
    ..To our knowledge, this is the first fluorinase enzyme to be identified, a discovery that opens up a new biotechnological opportunity for the preparation of organofluorine compounds...
  5. doi request reprint 3-fluoro-GABA enantiomers: exploring the conformation of GABA binding to GABAA receptors and GABA aminotransferase
    David O'Hagan
    School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK
    Future Med Chem 3:189-95. 2011
    ..This article describes how comparative analysis of these enantiomers has been used to assess the conformation of GABA binding to GABA(A) and the GABA-metabolizing enzyme, GABA transaminase...
  6. doi request reprint Understanding organofluorine chemistry. An introduction to the C-F bond
    David O'Hagan
    School of Chemistry and Centre for Biomolecular Science, University of St Andrews, North Haugh, St Andrews, UK KY16 9ST
    Chem Soc Rev 37:308-19. 2008
    ..In this tutorial review these fundamental aspects of the C-F bond are explored to rationalise the geometry, conformation and reactivity of individual organofluorine compounds...
  7. doi request reprint An enzymatic route to 5-deoxy-5-[18F]fluoro-D-ribose, a [18F]-fluorinated sugar for PET imaging
    Mayca Onega
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, UKKY16 9ST
    Chem Commun (Camb) 46:139-41. 2010
    ....
  8. pmc The fluorinase from Streptomyces cattleya is also a chlorinase
    Hai Deng
    School of Chemistry and Centre for Biomolecular Science, University of St Andrews, St Andrews, KY16 9ST, UK
    Angew Chem Int Ed Engl 45:759-62. 2006
  9. ncbi request reprint Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process
    Stephen Patterson
    School of Chemistry, Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Phytochemistry 61:323-9. 2002
    ..The data do not support an S-adenosy-L-methionine (SAM 5)/co-enzyme-B(12) mediated process for the isomerisation of littorine to hyoscyamine...
  10. ncbi request reprint The identification of 5'-fluoro-5-deoxyinosine as a shunt product in cell free extracts of Streptomyces cattleya
    Steven L Cobb
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, St Andrews, Fife, UK
    Bioorg Chem 33:393-401. 2005
    ....
  11. ncbi request reprint Crystallization and X-ray diffraction of 5'-fluoro-5'-deoxyadenosine synthase, a fluorination enzyme from Streptomyces cattleya
    Changjiang Dong
    Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, Scotland
    Acta Crystallogr D Biol Crystallogr 59:2292-3. 2003
    ..9, b = 130.3, c = 183.4 A, alpha = beta = gamma = 90 degrees. Data were recorded to 1.9 A at the ESRF. The structure of the protein should provide important insights into the biochemical process of C-F bond formation...
  12. doi request reprint In vitro reconstituted biotransformation of 4-fluorothreonine from fluoride ion: application of the fluorinase
    Hai Deng
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Chem Biol 15:1268-76. 2008
    ..The biotransformation demonstrates the power of the fluorinase to initiate C-F bond formation for organo-fluorine synthesis...
  13. ncbi request reprint Crystal structure and mechanism of a bacterial fluorinating enzyme
    Changjiang Dong
    Centre for Biomolecular Sciences, The University of St Andrews, Fife KY16 9ST, UK
    Nature 427:561-5. 2004
    ..Both substrate and products have been observed bound to the enzyme, enabling us to propose a nucleophilic substitution mechanism for this biological fluorination reaction...
  14. ncbi request reprint Cell-free biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya
    Christoph Schaffrath
    Centre for Biomolecular Sciences, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, UK
    Angew Chem Int Ed Engl 41:3913-5. 2002
  15. ncbi request reprint Assay for the enantiomeric analysis of [2H1]-fluoroacetic acid: insight into the stereochemical course of fluorination during fluorometabolite biosynthesis in streptomyces cattleya
    David O'Hagan
    School of Chemistry, University of St Andrews, Centre of Biomolecular Sciences, North Haugh, United Kingdom, KY15 9EA
    J Am Chem Soc 125:379-87. 2003
    ..Consequently, this outcome suggests that the stereochemical course of the recently identified fluorinase enzyme which mediates a reaction between fluoride ion and S-adenosyl-l-methionine (SAM), occurs with an inversion of configuration...
  16. pmc Substrate specificity in enzymatic fluorination. The fluorinase from Streptomyces cattleya accepts 2'-deoxyadenosine substrates
    Steven L Cobb
    School of Chemistry, Centre for Biomolecular Sciences, University of St Andrews, Purdie Building, North Haugh, St Andrews, KY16 9ST, UK
    Org Biomol Chem 4:1458-60. 2006
    ..It emerges from this study that the enzyme does not require a planar ribose conformation of the substrate to catalyse C-F bond formation...
  17. ncbi request reprint Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers
    Luke Hunter
    Centre for Biomolecular Sciences and School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Angew Chem Int Ed Engl 46:7887-90. 2007
  18. doi request reprint The rare fluorinated natural products and biotechnological prospects for fluorine enzymology
    K K Jason Chan
    EaStCHEM, School of Chemistry, University of St Andrews, St Andrews, United Kingdom
    Methods Enzymol 516:219-35. 2012
    ..This is particularly attractive, given the backdrop that about 15-20% of pharmaceuticals licensed each year (new chemical entities) contain a fluorine atom...
  19. ncbi request reprint Fluorometabolite biosynthesis and the fluorinase from Streptomyces cattleya
    Hai Deng
    School of Chemistry and Centre for Biomolecular Science, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK
    Nat Prod Rep 21:773-84. 2004
    ..Nature has hardly developed a biochemistry around fluorine, yet fluorinated organics are important commercial entities, therefore a biotransformation from inorganic to organic fluorine is novel and of contemporary interest...
  20. ncbi request reprint Enzymatic fluorination in Streptomyces cattleya takes place with an inversion of configuration consistent with an SN2 reaction mechanism
    Cosimo D Cadicamo
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, St Andrews, Fife, KY16 9ST, UK
    Chembiochem 5:685-90. 2004
    ..It is concluded that the enzyme catalyses the fluorination with an inversion of configuration consistent with an S(N)2 reaction mechanism...
  21. doi request reprint Fluorinase mediated chemoenzymatic synthesis of [(18)F]-fluoroacetate
    Xiang Guo Li
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Chem Commun (Camb) 46:7819-21. 2010
    ....
  22. doi request reprint S-adenosyl-L-methionine:hydroxide adenosyltransferase: a SAM enzyme
    Hai Deng
    Centre for Biomolecular Sciences, University of St Andrews, St Andrews KY16 9ST, UK
    Angew Chem Int Ed Engl 47:5357-61. 2008
  23. ncbi request reprint Isolation and characterisation of 5'-fluorodeoxyadenosine synthase, a fluorination enzyme from Streptomyces cattleya
    Christoph Schaffrath
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, KY16 9ST, St Andrews, UK
    FEBS Lett 547:111-4. 2003
    ..59 U/mg) have been evaluated. Both S-adenosyl-L-homocysteine (SAH) and sinefungin were explored as inhibitors of the enzyme. SAH emerged as a potent competitive inhibitor (K(i) 29 microM) whereas sinefungin was only weakly inhibitory...
  24. ncbi request reprint Enantioselective synthesis of an all-syn four vicinal fluorine motif
    Luke Hunter
    Centre for Biomolecular Sciences and School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, United Kingdom
    J Am Chem Soc 128:16422-3. 2006
    ..HC hydrogen bonding between adjacent fluoroalkyl chains...
  25. ncbi request reprint Allosteric agonists of the calcium receptor (CaR): fluorine and SF5 analogues of cinacalcet
    Poh Wai Chia
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Org Biomol Chem 10:7922-7. 2012
    ....
  26. doi request reprint Fluorocyclohexanes: synthesis and structure of all-syn-1,2,4,5-tetrafluorocyclohexane
    Alastair J Durie
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Chem Commun (Camb) 48:9643-5. 2012
    ..The all-syn isomer of 1,2,4,5-tetrafluorocyclohexane is prepared and characterised by NMR and X-ray crystallography. It emerges to be a particularly polar cyclohexane analogue with differentially polarised faces...
  27. doi request reprint Fluorinase: a tool for the synthesis of ¹⁸F-labeled sugars and nucleosides for PET
    Mayca Onega
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, KY16 9ST, Fife, UK
    Future Med Chem 1:865-73. 2009
    ..The focus is now on delivering a user-friendly catalyst to the PET synthesis community and establishing a clinical role for some of the (18)F-labeled molecules available using this technology...
  28. doi request reprint Diastereoselective synthesis of 2,3,4,5,6-pentafluoroheptanes
    Daniel Farran
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews KY16 9ST, United Kingdom
    J Org Chem 74:7168-71. 2009
    ....
  29. ncbi request reprint An electrostatic gauche effect in beta-fluoro- and beta-hydroxy-N-ethylpyridinium cations
    Natalie E J Gooseman
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Angew Chem Int Ed Engl 46:5904-8. 2007
  30. doi request reprint Insights into fluorometabolite biosynthesis in Streptomyces cattleya DSM46488 through genome sequence and knockout mutants
    Chunhua Zhao
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Bioorg Chem 44:1-7. 2012
    ..Notably gene disruption of the transaldolase (SCATT_p11780) resulted in a mutant which could produce fluoroacetate but was blocked in its ability to biosynthesise 4-fluorothreonine, revealing a branchpoint role for the PLP-transaldolase...
  31. doi request reprint Synthesis and structure of all-syn-1,2,3,4-tetrafluorocyclohexane
    Alastair J Durie
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Chem Commun (Camb) 47:8265-7. 2011
    ....
  32. ncbi request reprint Synthesis, conformation and biological evaluation of the enantiomers of 3-fluoro-gamma-aminobutyric acid ((R)- and (S)-3F-GABA): an analogue of the neurotransmitter GABA
    Gildas Deniau
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, St Andrews, Fife, KY16 9ST, Scotland, UK
    Chembiochem 8:2265-74. 2007
    ..A preliminary evaluation of the 3F-GABA enantiomers shows that they act similarly as agonists of cloned GABA(A) receptors; however, they behave quite differently in a whole animal (Xenopus laevis tadpole model)...
  33. ncbi request reprint Catalytic asymmetric fluorination comes of age
    Vincent A Brunet
    Centre for Biomolecular Sciences and School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Angew Chem Int Ed Engl 47:1179-82. 2008
  34. doi request reprint 3-Fluoro-N-methyl-D-aspartic acid (3F-NMDA) stereoisomers as conformational probes for exploring agonist binding at NMDA receptors
    Poh Wai Chia
    Department of Chemistry, Biomolecular Sciences Building, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Chemistry 18:8813-9. 2012
    ..These observations illustrate the utility of stereoselective fluorination in influencing the molecular conformation of β-fluorinated amino acids and thus probing the active conformations of bioactive compounds at receptors...
  35. doi request reprint The multi-vicinal fluoroalkane motif: an examination of 2,3,4,5-tetrafluorohexane stereoisomers
    Luke Hunter
    Centre for Biomolecular Sciences and School of Chemistry, University of St Andrews, St Andrews, United Kingdom
    Org Biomol Chem 6:3105-8. 2008
    ....
  36. ncbi request reprint Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya
    Cormac D Murphy
    School of Chemistry, Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife KY16 9ST, UK
    Chemosphere 52:455-61. 2003
    ..Studies with cell-free extracts of S. cattleya have identified two enzymes, an aldehyde dehydrogenase and a threonine transaldolase, that are involved in the biotransformation of fluoroacetaldehyde to fluoroacetate and 4-fluorothreonine...
  37. doi request reprint Accelerating influence of the gem-difluoromethylene group in a ring-closing olefin metathesis reaction. A Thorpe-Ingold effect?
    César A Urbina-Blanco
    EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Chem Commun (Camb) 49:7201-3. 2013
    ....
  38. doi request reprint Fluorinated 5- and 7-membered carbacycle motifs by reaction of difluorocarbene with acetylene ethers
    Poh Wai Chia
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Chem Commun (Camb) 49:2189-91. 2013
    ..The reaction of acetylene ethers with difluorocarbene (CF(2)), generated from the Ruppert-Prakash reagent, unexpectedly gave rise to co-produced fluorinated bicyclic [2.1.1]-hex-2-ene and cyclohepta-1,4-diene ring products...
  39. ncbi request reprint The Synthesis of η-1,2,3,4,5,6-Hexafluorocyclohexane (Benzene Hexafluoride) from Benzene
    Alastair J Durie
    EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST UK http chemistry st and ac uk staff doh group
    Angew Chem Int Ed Engl 51:10086-8. 2012
    ..Also starting from benzene, η-1,2,3,4,5,6-hexafluorocyclohexane (benzene hexafluoride; see X-ray structure of a dimer) was now synthesized in five steps...
  40. pmc The preferred conformation of erythro- and threo-1,2-difluorocyclododecanes
    Yi Wang
    EaStCHEM School of Chemistry, University of St Andrews, St Andrews, KY16 9ST, UK
    Beilstein J Org Chem 8:1271-8. 2012
    ..These structures avoid placing a C-F bond endo into the ring, and appear to benefit from C-CHF-C angle widening, which relaxes 1,4-H,H transannular interactions...
  41. doi request reprint The fluorinase, the chlorinase and the duf-62 enzymes
    Hai Deng
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife KY16 9ST, UK
    Curr Opin Chem Biol 12:582-92. 2008
    ..However structural examination of the duf-62 gene product reveals a very different organisation of the active site suggesting a novel mechanism for water activation...
  42. doi request reprint Multi-vicinal fluoroalkanes: a new class of organofluorine compounds
    Luke Hunter
    Centre for Biomolecular Sciences and School of Chemistry, University of St Andrews, St Andrews, United Kingdom
    Org Biomol Chem 6:2843-8. 2008
    ..This review will describe our recent progress in the preparation of such single isomer motifs and the study of the conformational behaviour of this new class of organofluorine compounds...
  43. doi request reprint Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis
    Pitak Nasomjai
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, St Andrews, Fife KY16 9ST, UK
    Chembiochem 10:2382-93. 2009
    ..The data suggest that hydroxylation takes place via a benzylic carbocation intermediate, whereas the product profile arising from rearrangement is more consistent with a benzylic radical intermediate...
  44. doi request reprint Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment
    Andrew Nortcliffe
    EaStCHEM School of Chemistry, Biomolecular Sciences Research Complex, University of St Andrews, North Haugh, St Andrews, Fife KY16 9ST, UK
    Bioorg Med Chem 22:756-61. 2014
    ..Compounds 1k and 1n exhibited significant cytotoxic with IC50 values of 6.1±4.1 and 12.1±3.2μM, respectively, coupled with observed nitric oxide release. ..
  45. doi request reprint The mechanisms of radical SAM/cobalamin methylations: an evolving working hypothesis
    K K Jason Chan
    Biomolecular Sciences Research Complex, EaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
    Chembiochem 14:675-7. 2013
    ....
  46. doi request reprint Fluorosugars: synthesis of the 2,3,4-trideoxy-2,3,4-trifluoro hexose analogues of D-glucose and D-altrose and assessment of their erythrocyte transmembrane transport
    Stefano Bresciani
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Chem Commun (Camb) 46:5434-6. 2010
    ....
  47. doi request reprint Novel amino acids: synthesis of furoxan and sydnonimine containing amino acids and peptides as potential nitric oxide releasing motifs
    Andrew Nortcliffe
    University of St Andrews, School of Chemistry and Centre for Biomolecular Sciences, North Haugh, St Andrews, Fife KY16 9ST, UK
    Org Biomol Chem 11:4657-71. 2013
    ..By way of demonstration the amino acids were placed centrally into several tripeptide motifs. Griess test assays showed that these amino acids released NO in the presence of γ-glutathione (GST). ..
  48. pmc Prins fluorination cyclisations: Preparation of 4-fluoro-pyran and -piperidine heterocycles
    Guillaume G Launay
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, United Kingdom
    Beilstein J Org Chem 6:41. 2010
    ..These Prins fluorination reactions can be accelerated under microwave conditions. The study extends the Prins fluorination methodology for the generation of the C-F bond in heterocycles...
  49. pmc Three step synthesis of single diastereoisomers of the vicinal trifluoro motif
    Vincent A Brunet
    School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Beilstein J Org Chem 5:61. 2009
    ..Starting from either the syn- or the anti-alpha,beta-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy...
  50. pmc Single enantiomer synthesis of α-(trifluoromethyl)-β-lactam
    Václav Jurčík
    EASTChem School of Chemistry and Centre for Biomolecular Sciences, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK
    Beilstein J Org Chem 7:759-66. 2011
    ....