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Meghan Campbell, J. Wengel (2011)
Locked vs. unlocked nucleic acids (LNA vs. UNA): contrasting structures work towards common therapeutic goals.Chemical Society reviews, 40 12
K. Kowalski, Łukasz Szczupak, S. Saloman, D. Steverding, Artur Jabłoński, Valerije Vrček, Alexander Hildebrandt, H. Lang, A. Rybarczyk-Pirek (2017)
Cymantrene, Cyrhetrene and Ferrocene Nucleobase Conjugates: Synthesis, Structure, Computational Study, Electrochemistry and Antitrypanosomal Activity.ChemPlusChem, 82 2
Vitor Pinheiro, Alexander Taylor, Christopher Cozens, M. Abramov, M. Renders, Su Zhang, J. Chaput, J. Wengel, S. Peak-Chew, S. McLaughlin, P. Herdewijn, P. Holliger (2012)
Synthetic Genetic Polymers Capable of Heredity and EvolutionScience, 336
Jonathan Kedge, H. Nguyen, Zahra Khan, L. Male, Holly Ismail, S. Horswell, Y. Mehellou, J. Tucker (2017)
Organometallic Nucleoside Analogues: Effect of Hydroxyalkyl Linker Length on Cancer Cell Line ToxicityEuropean Journal of Inorganic Chemistry, 2017
Michal Hocek, P. Štěpnička, J. Ludvík, I. Císařová, I. Votruba, D. Řeha, P. Hobza (2004)
Ferrocene-modified purines as potential electrochemical markers: synthesis, crystal structures, electrochemistry and cytostatic activity of (ferrocenylethynyl)- and (ferrocenylethyl)purines.Chemistry, 10 8
J. Skiba, C. Schmidt, P. Lippmann, P. Ensslen, H. Wagenknecht, R. Czerwieniec, Fabian Brandl, I. Ott, T. Bernaś, B. Krawczyk, D. Szczukocki, K. Kowalski (2017)
Substitution of Metallocenes with [2.2]Paracyclophane to Enable Confocal Microscopy Imaging in Living CellsEuropean Journal of Inorganic Chemistry
P. Herdewijn (2010)
Nucleic Acids with a Six‐Membered ‘Carbohydrate’ Mimic in the BackboneChemistry & Biodiversity, 7
T. Alam, G. Drobny (1991)
Solid-state NMR studies of DNA structure and dynamicsChemical Reviews, 91
C. Wilds, M. Damha (2000)
2'-Deoxy-2'-fluoro-beta-D-arabinonucleosides and oligonucleotides (2'F-ANA): synthesis and physicochemical studies.Nucleic acids research, 28 18
K. Kowalski, J. Skiba, Luciano Oehninger, I. Ott, J. Solecka, A. Rajnisz, B. Therrien (2013)
Metallocene-Modified Uracils: Synthesis, Structure, and Biological ActivityOrganometallics, 32
O. Avery, C. MacLeod, M. McCarty (1979)
Studies on the chemical nature of the substance inducing transformation of pneumococcal types. Inductions of transformation by a desoxyribonucleic acid fraction isolated from pneumococcus type IIIThe Journal of Experimental Medicine, 149
J. Furrer, G. Süss-Fink (2016)
Thiolato-bridged dinuclear arene ruthenium complexes and their potential as anticancer drugsCoordination Chemistry Reviews, 309
Alexander Hildebrandt, K. Khalyfeh, Dieter Schaarschmidt, M. Korb (2016)
Multi-functionalized ferrocenes: –Synthesis and characterization –Journal of Organometallic Chemistry, 804
A. Noronha, C. Wilds, C. Lok, Katya Viazovkina, D. Arion, M. Parniak, M. Damha (2000)
Synthesis and biophysical properties of arabinonucleic acids (ANA): circular dichroic spectra, melting temperatures, and ribonuclease H susceptibility of ANA.RNA hybrid duplexes.Biochemistry, 39 24
A. Marenich, C. Cramer, D. Truhlar (2009)
Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions.The journal of physical chemistry. B, 113 18
G. Jaouen, A. Vessières, S. Top (2015)
Ferrocifen type anti cancer drugs.Chemical Society reviews, 44 24
C. Ornelas (2011)
Application of ferrocene and its derivatives in cancer researchNew Journal of Chemistry, 35
J. Shelton, Xiao Lu, Joseph Hollenbaugh, Jong-Hyun Cho, F. Amblard, R. Schinazi (2016)
Metabolism, Biochemical Actions, and Chemical Synthesis of Anticancer Nucleosides, Nucleotides, and Base Analogs.Chemical reviews, 116 23
Jing Wang, B. Verbeure, I. Luyten, E. Lescrinier, M. Froeyen, C. Hendrix, H. Rosemeyer, F. Seela, A. Aerschot, P. Herdewijn (2000)
Cyclohexene Nucleic Acids (CeNA): Serum Stable Oligonucleotides that Activate RNase H and Increase Duplex Stability with Complementary RNAJournal of the American Chemical Society, 122
C. Faralli, M. Pagliai, G. Cardini, V. Schettino (2007)
The solvation dynamics of Na+ and K+ ions in liquid methanolTheoretical Chemistry Accounts, 118
D. Wigfield (1979)
Stereochemistry and mechanism of ketone reductions by hydride reagentsTetrahedron, 35
F. Barrière, W. Geiger (2006)
Use of weakly coordinating anions to develop an integrated approach to the tuning of deltaE(1/2) values by medium effects.Journal of the American Chemical Society, 128 12
K. Schöning, P. Scholz, S. Guntha, X. Wu, R. Krishnamurthy, A. Eschenmoser (2000)
Chemical Etiology of Nucleic Acid Structure: The α-Threofuranosyl-(3'→2') Oligonucleotide SystemScience, 290
Matteo Iurlo, L. Mengozzi, S. Rapino, M. Marcaccio, R. Perone, S. Masiero, P. Cozzi, F. Paolucci (2014)
New Approaches toward Ferrocene–Guanine Conjugates: Synthesis and Electrochemical BehaviorOrganometallics, 33
J. Watson, F. Crick (1953)
Molecular Structure of Nucleic Acids: A Structure for Deoxyribose Nucleic AcidNature, 171
K. Kowalski, A. Koceva-Chyła, A. Pieniazek, J. Bernasińska, J. Skiba, A. Rybarczyk-Pirek, Z. Jóźwiak (2012)
The synthesis, structure, electrochemistry and in vitro anticancer activity studies of ferrocenyl-thymine conjugatesJournal of Organometallic Chemistry, 700
Avery (1944)
137J. Exp. Med., 79
P. Herdewijn, P. Marlière (2009)
Toward Safe Genetically Modified Organisms through the Chemical Diversification of Nucleic AcidsChemistry & Biodiversity, 6
K. Kowalski (2016)
Ferrocenyl-nucleobase complexes: Synthesis, chemistry and applicationsCoordination Chemistry Reviews, 317
G. Sheldrick (2008)
A short history of SHELX.Acta crystallographica. Section A, Foundations of crystallography, 64 Pt 1
Yasumitsu Suzuki, D. Kaneno, S. Tomoda (2009)
Theoretical study on the mechanism and diastereoselectivity of NaBH4 reduction.The journal of physical chemistry. A, 113 11
Søren Preus (2012)
is part of the Nucleic acids : new life , new materials web ‐ themed
Hellen Dyer, S. Huijser, N. Susperregui, F. Bonnet, Andrew Schwarz, R. Duchateau, L. Maron, P. Mountford (2010)
Ring-Opening Polymerization of rac-Lactide by Bis(phenolate)amine-Supported Samarium Borohydride Complexes: An Experimental and DFT StudyOrganometallics, 29
A. Wachters (1970)
Gaussian Basis Set for Molecular Wavefunctions Containing Third‐Row AtomsJournal of Chemical Physics, 52
L. Farrugia (1997)
ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI)Journal of Applied Crystallography, 30
Alexander Hildebrandt, Dieter Schaarschmidt, H. Lang (2011)
Electronically Intercommunicating Iron Centers in Di- and Tetraferrocenyl Pyrroles§Organometallics, 30
Alexander Taylor, P. Holliger (2015)
Directed evolution of artificial enzymes (XNAzymes) from diverse repertoires of synthetic genetic polymersNature Protocols, 10
A. Hershey, M. Chase (1952)
INDEPENDENT FUNCTIONS OF VIRAL PROTEIN AND NUCLEIC ACID IN GROWTH OF BACTERIOPHAGEThe Journal of General Physiology, 36
M. Patra, G. Gasser, N. Metzler‐Nolte (2012)
Small organometallic compounds as antibacterial agents.Dalton transactions, 41 21
I. Ott (2009)
On the medicinal chemistry of gold complexes as anticancer drugsCoordination Chemistry Reviews, 253
N. Barros, P. Mountford, Sophie Guillaume, L. Maron (2008)
A DFT study of the mechanism of polymerization of epsilon-caprolactone initiated by organolanthanide borohydride complexes.Chemistry, 14 18
G. Gritzner, J. Kůta (1984)
Recommendations on reporting electrode potentials in nonaqueous solvents (Recommendations 1983)Pure and Applied Chemistry, 56
E. Meggers, Lilu Zhang (2010)
Synthesis and properties of the simplified nucleic acid glycol nucleic acid.Accounts of chemical research, 43 8
A. Becke (1993)
Density-functional thermochemistry. III. The role of exact exchangeJournal of Chemical Physics, 98
The synthesis of 1,1′‐bis(thymine)ferrocene nucleoside is reported. This nucleoside was obtained in a two‐step synthetic methodology including a Michael addition reaction of 1,1′‐bis(3‐chloropropionyl)ferrocene with thymine to afford the bis(thymine) adduct in 44 % yield. In the second step, the two prochiral carbonyl functionalities in the Michael adduct were reduced to hydroxyl groups with sodium borohydride. This apparently straightforward reaction proceeds in a highly stereoselective fashion to yield the title ferrocenyl nucleoside as a racemic mixture that consists of the R,R and the S,S isomers. The absolute configuration of the chiral carbon atoms in the nucleoside was assigned on the basis of single‐crystal X‐ray diffraction analysis of the methyl derivative. Furthermore, the mechanism of reduction of the bis(thymine) adduct was investigated by using DFT calculations. The two critical minima, pre‐reactive complex, and semi‐reduced intermediate, as well as two corresponding transition states were located to support the observed stereoselectivity. The redox properties of 1,1′‐bis(thymine)ferrocene nucleoside, its precursor, and congeners were investigated using cyclic voltammetry. For the title compound a reversible redox process was found at a low potential of −30 mV versus FcH/FcH+ (FcH=Fe(η5‐C5H5)2) as the reference redox couple.
ChemPlusChem – Wiley
Published: Jun 1, 2017
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