| 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 |
Yusof ENM, Latif MAM, Tahir MIM, Sakoff JA, Simone MI, 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)
Six new organotin(IV) compounds of Schiff bases derived from S-R-dithiocarbazate [R = benzyl (B), 2- or 4-methylbenzyl (2M and 4M, respectively)] condensed with 2-hydroxy-3-methox... [more] Six new organotin(IV) compounds of Schiff bases derived from S-R-dithiocarbazate [R = benzyl (B), 2- or 4-methylbenzyl (2M and 4M, respectively)] condensed with 2-hydroxy-3-methoxybenzaldehyde (oVa) were synthesised and characterised by elemental analysis, various spectroscopic techniques including infrared, UV-vis, multinuclear (¹H, 13C, 119Sn) NMR and mass spectrometry, and single crystal X-ray diffraction. The organotin(IV) compounds were synthesised from the reaction of Ph2SnCl2 or Me2SnCl2 with the Schiff bases (S2MoVaH/S4MoVaH/SBoVaH) to form a total of six new organotin(IV) compounds that had a general formula of [R2Sn(L)] (where L = Schiff base; R = Ph or Me). The molecular geometries of Me2Sn(S2MoVa), Me2Sn(S4MoVa) and Me2Sn(SBoVa) were established by X-ray crystallography and verified using density functional theory calculations. Interestingly, each experimental structure contained two independent but chemically similar molecules in the crystallographic asymmetric unit. The coordination geometry for each molecule was defined by thiolate-sulphur, phenoxide-oxygen and imine-nitrogen atoms derived from a dinegative, tridentate dithiocarbazate ligand with the remaining positions occupied by the methyl-carbon atoms of the organo groups. In each case, the resulting five-coordinate C2NOS geometry was almost exactly intermediate between ideal trigonal-bipyramidal and square-pyramidal geometries. The cytotoxic activities of the Schiff bases and organotin(IV) compounds were investigated against EJ-28 and RT-112 (bladder), HT29 (colon), U87 and SJ-G2 (glioblastoma), MCF-7 (breast) A2780 (ovarian), H460 (lung), A431 (skin), DU145 (prostate), BE2-C (neuroblastoma) and MIA (pancreatic) cancer cell lines and one normal breast cell line (MCF-10A). Diphenyltin(IV) compounds exhibited greater potency than either the Schiff bases or the respective dimethyltin(IV) compounds. Mechanistic studies on the action of these compounds against bladder cancer cells revealed that they induced the production of reactive oxygen species (ROS). The bladder cancer cells were apoptotic after 24 h post-treatment with the diphenyltin(IV) compounds. The interactions of the organotin(IV) compounds with calf thymus DNA (CT-DNA) were experimentally explored using UV-vis absorption spectroscopy. This study revealed that the organotin(IV) compounds have strong DNA binding affinity, verified via molecular docking simulations, which suggests that these organotin(IV) compounds interact with DNA via groove-binding interactions.
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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, 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, 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]
© 2015 The Royal Society of Chemistry. The protein kinase inhibitor CTx-0152960 (6, 2-((5-chloro-2-((4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), and the pip... [more] © 2015 The Royal Society of Chemistry. 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]
© The Royal Society of Chemistry 2014. A commonly observed limitation of conducting hydrogenations under flow chemistry conditions is hydrodehalogenation. In a bid to circumvent t... [more] © The Royal Society of Chemistry 2014. 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)
© 2014 The Authors. Published by Elsevier Ltd. A novel series of 8-amino imidazo[1,2-a]pyrazine derivatives has been developed as inhibitors of the VirB11 ATPase HP0525, a key com... [more] © 2014 The Authors. Published by Elsevier Ltd. 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, 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-STRUCTURE REPORTS ONLINE, 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-STRUCTURE REPORTS ONLINE, 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-STRUCTURE REPORTS ONLINE, 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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