| 2021 |
Glenister A, Chen CKJ, Paterson DJ, Renfrew AK, Simone MI, Hambley TW, 'Warburg Effect Targeting Co(III) Cytotoxin Chaperone Complexes', Journal of Medicinal Chemistry, 64 2678-2690 (2021) [C1]
A glucose-based vector for targeting cancer cells conjugated to a tris(methylpyridyl)amine (tpa) ligand to generate targeted chaperone and caging complexes for active anticancer a... [more] A glucose-based vector for targeting cancer cells conjugated to a tris(methylpyridyl)amine (tpa) ligand to generate targeted chaperone and caging complexes for active anticancer agents is described. The ligand, tpa(CONHPEGglucose)1, inhibits hexokinase, suggesting that it will be phosphorylated in the cell. A Co(III) complex incorporating this ligand and coumarin-343 hydroximate (C343ha), [Co(C343ha){tpa(CONHPEGglucose)1}]Cl, is shown to exhibit glucose-dependent cellular accumulation in DLD-1 colon cancer cells. Cellular accumulation of [Co(C343ha){tpa(CONHPEGglucose)1}]+ is slower than for the glucose null and glucosamine analogues, and the glucose complex also exhibits a lower ability to inhibit antiproliferative activity. Distributions of cobalt (X-ray fluorescence) and C343ha (visible light fluorescence) in DLD-1 cancer cell spheroids are consistent with uptake of [Co(C343ha){tpa(CONHPEGglucose)1}]+ by rapidly dividing cells, followed by release and efflux of C343ha and trapping of the Co{tpa(CONHPEGglucose)1} moiety. The Co{tpa(CONHPEGglucose)1} moiety is shown to have potential for the caged and targeted delivery of highly toxic anticancer agents.
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| 2020 |
Yusof ENM, Page AJ, Sakoff JA, Simone MI, Veerakumarasivam A, Tiekink ERT, Ravoof TBSA, 'Tin(IV) compounds of tridentate thiosemicarbazone Schiff bases: Synthesis, characterization, in-silico analysis and in vitro cytotoxicity', Polyhedron, 189 (2020) [C1]
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| 2020 |
Wood A, Bernhardt PV, van Altena I, Simone MI, 'Crystal structure of 6-azido-6-deoxy-1,2-O-isopropylidene-a-D-glucofuranose', Acta Crystallographica Section E Crystallographic Communications, 76 1653-1656 (2020) [C1]
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| 2020 |
Ghorbani M, Bernhardt PV, Simone MI, 'Structural characterisation of new ionic liquids via X-ray crystallography', Journal of Molecular Liquids, 319 (2020) [C1]
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| 2020 |
Ghorbani M, Simone MI, 'Developing New Inexpensive Room-Temperature Ionic Liquids with High Thermal Stability and a Greener Synthetic Profile', ACS Omega, 5 12637-12648 (2020) [C1]
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| 2019 |
Pappin B, Garget T, Healy P, Simone M, Kiefel M, Houston T, 'Facile amidinations of 2-aminophenylboronic acid promoted by boronate ester formation', Organic & Biomolecular Chemistry, 17 803-806 (2019) [C1]
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| 2019 |
Nadia Md Yusof E, Latif MAM, Tahir MIM, Sakoff J, Simone M, Page AJ, et al., 'o-Vanillin Derived Schiff Bases and Their
Organotin(IV) Compounds: Synthesis, Structural
Characterisation, In-Silico Studies and Cytotoxicity', International Journal of Molecular Sciences, 20 (2019) [C1]
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| 2019 |
Glenister A, Simone MI, Hambley TW, 'A Warburg effect targeting vector designed to increase the uptake of compounds by cancer cells demonstrates glucose and hypoxia dependent uptake', PLOS ONE, 14 (2019) [C1]
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| 2018 |
Simone MI, Mares LJ, Eveleens CA, McCluskey A, Pappin BB, Kiefel MJ, Houston TA, 'Back to (non-)Basics: An Update on Neutral and Charge-Balanced Glycosidase Inhibitors', MINI-REVIEWS IN MEDICINAL CHEMISTRY, 18 812-827 (2018) [C1]
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| 2018 |
Nadia Md Yusof E, Tiekink ERT, Jotani MM, Simone M, Page A, Begum T, 'Synthesis, characterisation and structure determination of 3-[(1Z)-{2-[bis({[(2-methylphenyl)methyl]sulfanyl})methylidene]hydrazin-1-ylidene}methyl]benzene-1,2-diol', JOURNAL OF MOLECULAR STRUCTURE, 1171 650-657 (2018) [C1]
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| 2018 |
Prichard K, Campkin D, O'Brien N, Kato A, Fleet GWJ, Simone MI, 'Biological activities of 3,4,5-trihydroxypiperidines and their N- and O-derivatives', CHEMICAL BIOLOGY & DRUG DESIGN, 92 1171-1197 (2018) [C1]
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| 2018 |
Wood A, Prichard KL, Clarke Z, Houston TA, Fleet GWJ, Simone MI, 'Synthetic Pathways to 3,4,5-Trihydroxypiperidines from the Chiral Pool', EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018 6812-6829 (2018) [C1]
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| 2018 |
Prichard KL, O'Brien N, Ghorbani M, Wood A, Barnes E, Kato A, et al., 'Synthetic Routes to 3,4,5-Trihydroxypiperidines via Stereoselective and Biocatalysed Protocols, and Strategies to N- and O-Derivatisation', EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018 6830-6842 (2018) [C1]
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| 2018 |
Clarke Z, Barnes E, Prichard K, Mares L, Clegg J, McCluskey A, et al., 'The crystal structures of 3-O-benzyl-1,2-O-isopropylidene-
5-O-methanesulfonyl-6-O-triphenylmethyl-
a-D-glucofuranose and its azide
displacement product', Acta Crystallographica Section E, 74 862-867 (2018) [C1]
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| 2017 |
Langron E, Simone MI, Delalande CMS, Raymond J-L, Selwood DL, Vergani P, 'Improved fluorescence assays to measure the defects
associated with F508del-CFTR allow identification of new
active compounds', BRITISH JOURNAL OF PHARMACOLOGY, 174 525-539 (2017) [C1]
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| 2017 |
Latham KG, Simone M, Dose WM, Allen JA, Donne SW, 'Synchrotron based NEXAFS study on nitrogen doped hydrothermal
carbon: Insights into surface functionalities and formation
mechanisms', Carbon, 114 566-578 (2017) [C1]
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| 2017 |
Pappin BB, Levonis ML, Healy PC, Kiefel MJ, Simone M, Houston TA, 'Crystallization-induced amide bond formation creates a boron-centered spirocyclic system', Heterocyclic Communications, 23 167-169 (2017) [C1]
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| 2016 |
Warne J, Pryce G, Hill J, Shi X, Lennerås F, Puentes F, et al., 'Selective inhibition of the mitochondrial permeability transition pore protects against neurodegeneration in experimental multiple sclerosis', Journal of Biological Chemistry, 291 4356-4373 (2016) [C1]
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| 2015 |
Cossar PJ, Hizartzidis L, Simone M, McCluskey A, Gordon CP, 'The expanding utility of continuous flow hydrogenation', Organic and Biomolecular Chemistry, 26 7119-7130 (2015) [C1]
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| 2015 |
Russell C, Lin AJS, Hains P, Simone MI, Robinson PJ, Mccluskey A, 'An integrated flow and microwave approach to a broad spectrum protein kinase inhibitor', RSC Advances, 5 93433-93437 (2015) [C1]
The protein kinase inhibitor CTx-0152960 (6, 2-((5-chloro-2-((4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), and the piperazinyl analogue, CTx-0294885 (7, 2-((... [more] The protein kinase inhibitor CTx-0152960 (6, 2-((5-chloro-2-((4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), and the piperazinyl analogue, CTx-0294885 (7, 2-((5-chloro-2-((4-piperazin-1-ylphenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), were prepared using a hybrid flow and microwave approach. The use of flow chemistry approaches avoided the need for Boc-protection of piperidine in the key SNAr coupling with 1-fluoro-4-nitrobenzene. Microwave coupling of 4-morphilinoaniline 8 and 4-(piperazine-1-yl)aniline 9 with 2-(2,5-dichloropyrimidine-4-ylamino)-N-methylbenzamide 10, proved to be the most efficacious route to the target analogues 6 and 7. This hybrid methodology reduced the number of synthetic steps, gave enhanced overall yields and increased atom economy through step reduction and minimal requirement for chromatographic purification, relative to the original batch synthesis approach.
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| 2015 |
Warne J, Pryce G, Hill J, Shi X, Lenneras F, Puentes F, et al., 'Crystal structure of cyclophilin D in complex with CsA analogue, JW47. PDB Code 5A0E', RCSB Protein Databank Archive: PDB, (2015) [O1]
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| 2014 |
Simone MI, Houston TA, 'A Brief Overview of Recent Advances in the Applications of Boronic Acids Relevant to Glycomics', Journal of Glycomics & Lipidomics, 4 e124-e124 (2014) [C3]
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| 2014 |
Hizartzidis L, Cossar PJ, Robertson MJ, Simone MI, Young KA, McCluskey A, Gordon CP, 'Expanding the utility of flow hydrogenation - A robust protocol restricting hydrodehalogenation', RSC Advances, 4 56743-56748 (2014) [C1]
A commonly observed limitation of conducting hydrogenations under flow chemistry conditions is hydrodehalogenation. In a bid to circumvent this limitation a series of hydrogenatio... [more] A commonly observed limitation of conducting hydrogenations under flow chemistry conditions is hydrodehalogenation. In a bid to circumvent this limitation a series of hydrogenation catalysts were screened, with 5% Pt/C (sulfided) catalyst identified as an effective catalyst to selectively effect reductive aminations, nitro reduction, and alkene reductions in the presence of halogen atoms. Additionally the optimised protocol cleanly reduced imines in the presence of a furan moiety indicating potential amenability to other labile functionalities.
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| 2014 |
Moyes AJ, Khambata RS, Villar I, Bubb KJ, Baliga RS, Lumsden NG, et al., 'Endothelial C-type natriuretic peptide maintains vascular homeostasis', Journal of Clinical Investigation, 1 (2014) [C1]
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| 2014 |
Sayer JR, Walldén K, Pesnot T, Campbell F, Gane PJ, Simone M, et al., '2- and 3-substituted imidazo[1,2-a]pyrazines as inhibitors of bacterial type IV secretion', Bioorganic and Medicinal Chemistry, 22 6459-6470 (2014)
A novel series of 8-amino imidazo[1,2-a]pyrazine derivatives has been developed as inhibitors of the VirB11 ATPase HP0525, a key component of the bacterial type IV secretion syste... [more] A novel series of 8-amino imidazo[1,2-a]pyrazine derivatives has been developed as inhibitors of the VirB11 ATPase HP0525, a key component of the bacterial type IV secretion system. A flexible synthetic route to both 2- and 3-aryl substituted regioisomers has been developed. The resulting series of imidazo[1,2-a]pyrazines has been used to probe the structure-activity relationships of these inhibitors, which show potential as antibacterial agents.
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| 2013 |
Risseeuw M, Overhand M, Fleet GWJ, Simone MI, 'A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues', Amino Acids, 45 613-689 (2013) [C1]
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| 2013 |
Reed JH, Turner P, Kato A, Houston TA, Simone M, '1-O-Benzyl-2,3-O-isopropylidene-6-O-tosyl-a-L-sorbofuranose', Acta Crystallographica Section E: Structure Reports Online, 69 o1069-o1070 (2013) [C1]
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| 2012 |
Gooding M, Tudzarova S, Worthington RJ, Kingsbury SR, Rebstock AS, Dube H, et al., 'Exploring the interaction between siRNA and the SMoC biomolecule transporters: Implications for small molecule-mediated delivery of siRNA', Chemical Biology and Drug Design, 79 9-21 (2012)
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| 2012 |
Dube H, Selwood D, Malouitre S, Capano M, Simone MI, Crompton M, 'A mitochondrial-targeted cyclosporin A with high binding affinity for cyclophilin D yields improved cytoprotection of cardiomyocytes', BIOCHEMICAL JOURNAL, 441 901-907 (2012) [C1]
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| 2012 |
Simone MI, Soengas RG, Jenkinson SF, Evinson EL, Nash RJ, Fleet GWJ, 'Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3.4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2', TETRAHEDRON-ASYMMETRY, 23 401-408 (2012) [C1]
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| 2012 |
Soengas RG, Simone MI, Hunter S, Nash RJ, Evinson EL, Fleet GWJ, 'Hydroxymethyl-Branched Piperidines from Hydroxymethyl-Branched Lactones: Synthesis and Biological Evaluation of 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-mannitol, 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-L-gulitol and 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-talitol', EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012 2394-2402 (2012) [C1]
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| 2012 |
Jenkinson SF, Thompson AL, Simone MI, 'Methyl 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-nitrobenzoate', Acta Crystallographica Section E: Structure Reports Online, 68 o2429-o2430 (2012) [C1]
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| 2011 |
Simone MI, Edwards AA, Tranter GE, Fleet GWJ, 'C-3 branched delta-3,5-cis- and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers', AMINO ACIDS, 41 643-661 (2011) [C1]
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| 2010 |
Simone MI, Edwards AA, Parker SG, Tranter GE, Fleet GWJ, Watkin DJ, 'Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido] methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 66 O2699-U1584 (2010) [C1]
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| 2010 |
Simone MI, Edwards AA, Cowley AR, Fleet GWJ, Watkin DJ, '(3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide', ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 66 O2750-U2003 (2010) [C1]
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| 2009 |
Hobbs AJ, Gane P, Lumsden N, Nobles M, Rebstock A-S, Simone M, et al., 'Design and development of novel non-peptide agonists at natriuretic peptide receptor-C', FASEB JOURNAL, 23 (2009) [E3] |
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| 2008 |
Simone MI, Edwards AA, Tranter GE, Fleet GWJ, 'Carbon-branched delta-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds', TETRAHEDRON-ASYMMETRY, 19 2887-2894 (2008) [C1]
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| 2007 |
Risseeuw MDP, Overhand M, Fleet GWJ, Simone MI, 'A compendium of sugar amino acids (SAA): scaffolds, peptide- and glyco-mimetics', TETRAHEDRON-ASYMMETRY, 18 2001-2010 (2007)
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| 2007 |
Simone M, Fleet GWJ, Watkin DJ, '3,3': 5,6-Di-O-isopropylidene-3-C-hydroxy-methyl-(D)-allono-1,4-lactone: an organic structure containing large unoccupied voids', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 63 O799-O801 (2007)
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| 2007 |
Simone M, Fleet GWJ, Watkin DJ, '1,5-Anhydro-2,3-O-isopropylidene-L-lyxo-furanose [(1S,4S,5S,6R)-5,6-O-isopropylidene-2,7-dioxabicyclo[2.2.1]heptane-5,6-diol]', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 63 O896-O897 (2007)
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| 2007 |
Simone M, Fleet GWJ, Watkin DJ, '5-O-tert-butyldiphenylsilyl-2-C-hydroxymethyl-2,3-O-isopropylidene-2 ' O-trifluoromethanesulfonyl-D-ribono-1,4-lactone', ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 63 o1088-o1090 (2007)
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| 2007 |
Simone M, Fleet GWJ, Bream R, Watkin DJ, '5-Amino-5-deoxy-2-C-hydroxymethyl-2,3-O-iso-propylidene-(L)-lyxono-1,5-lactam', ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 63 o1409-o1411 (2007)
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| 2006 |
Bleriot Y, Simone MI, Wormald MR, Dwek RA, Watkin DJ, Fleet GWJ, 'Sugar amino acids at the anomeric position of carbohydrates: synthesis of spirocyclic amino acids of 6-deoxy-L-lyxofuranose', TETRAHEDRON-ASYMMETRY, 17 2276-2286 (2006)
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| 2006 |
Punzo F, Cowley AR, Watkin DJ, Simone MI, Edwards AA, Tranter GE, Fleet GWJ, 'Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydro-furan-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 62 O473-O475 (2006)
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| 2006 |
Parker SG, Watkin DJ, Simone MI, Fleet GWJ, '3,4 : 5,6-di-O-isopropylidene-3-C-hydroxy-methyl-D-altrono-1,3 '-lactone', ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 62 O3961-O3963 (2006)
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| 2006 |
Jockusch RA, Talbot FO, Rogers PS, Simone MI, Fleet GWJ, Simons JP, 'Carbohydrate amino acids: The intrinsic conformational preference for a beta-turn-type structure in a carbopeptoid building block', JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 128 16771-16777 (2006)
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| 2005 |
Punzo F, Watkin DJ, Simone MI, Fleet GWJ, '(3R,4R,5S)-5-(acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 61 O513-O515 (2005)
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| 2005 |
Soengas R, Izumori K, Simone MI, Watkin DJ, Skytte UP, Soetaert W, Fleet GWJ, 'Kiliani reactions on ketoses: branched carbohydrate building blocks from D-tagatose and D-psicose', TETRAHEDRON LETTERS, 46 5755-5759 (2005)
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| 2005 |
Simone MI, Soengas R, Newton CR, Watkin DJ, Fleet GWJ, 'Branched tetrahydrofuran alpha,alpha-disubstituted-delta-sugar amino acid scaffolds from branched sugar lactones: a new family of foldamers?', TETRAHEDRON LETTERS, 46 5761-5765 (2005)
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| 2004 |
Hotchkiss D, Soengas R, Simone MI, van Ameijde J, Hunter S, Cowley AR, Fleet GWJ, 'Kiliani on ketoses: branched carbohydrate building blocks from D-fructose and L-sorbose', TETRAHEDRON LETTERS, 45 9461-9464 (2004)
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| 2004 |
Newton CR, Michela IS, Fleet GWJ, Bleriot Y, Watkin DJ, '2-C-hydroxymethyl-2,3-O-isopropylidene-D-ribono-1,5-lactam', ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 60 O909-O910 (2004)
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| 2004 |
Watkins DJ, Muller M, Bleriot Y, Simone MI, Fleet GWJ, '(2S,3R,4R,5S)-3,4-O-isopropylidene-2-methyl-1-oxa-6,9-diazaspiro[4.5]decane-7,10-dione', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 60 O1820-O1822 (2004)
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| 2004 |
van Ameijde J, Cowley AR, Fleet GWJ, Nash RJ, Simone MI, Soengas R, '5-amino-5-deoxy-2-C-hydroxymethyl-2,3-O-isopropylidene-D-talono-1,5-lactam', ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 60 O2140-O2141 (2004)
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| 2004 |
Cowley AR, Fleet GWJ, Simone MI, Soengas R, '3-O-tert-butyldimethylsilyl-2,2 ': 5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-1,4-gluconolactone', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 60 O2142-O2143 (2004)
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| 2004 |
Punzo F, Watkin DJ, Simone MI, Fleet GWJ, '(1R,5S,8R)-1,8-dihydroxy-6-oxa-3-azabicyclo[3.2.1]octan-2-one', ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 60 O2315-O2317 (2004)
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Legge WJ, Shimadate Y, Ghorbani M, Sakoff J, Houston TA, Kato A, et al., 'Borylated methyl cinnamates: Expedited synthesis, characterization, crystallographic analysis and biological activities in glycosidase inhibition and in cancer cells lines.
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