C-nucleosides: synthetic strategies and biological applications.

PubWeight™: 1.12‹?› | Rank: Top 10%

🔗 View Article (PMID 19761208)

Published in Chem Rev on December 01, 2009

Authors

Jan Stambaský1, Michal Hocek, Pavel Kocovský

Author Affiliations

1: Department of Chemistry, WestChem, University of Glasgow, Glasgow G12 8QQ, United Kingdom.

Articles citing this

Emissive RNA alphabet. J Am Chem Soc (2011) 1.22

DNA-multichromophore systems. Chem Rev (2012) 1.10

The Expanded Genetic Alphabet. Angew Chem Int Ed Engl (2015) 0.95

Expanding the scope of replicable unnatural DNA: stepwise optimization of a predominantly hydrophobic base pair. J Am Chem Soc (2013) 0.91

Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects. J Org Chem (2013) 0.85

Chemical Mutagenesis of an Emissive RNA Alphabet. J Am Chem Soc (2015) 0.79

C-5'-Triazolyl-2'-oxa-3'-aza-4'a-carbanucleosides: Synthesis and biological evaluation. Beilstein J Org Chem (2015) 0.77

A general and enantioselective approach to pentoses: a rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir. J Am Chem Soc (2014) 0.76

Synthesis of 2'-deoxy-9-deaza nucleosides using Heck methodology. J Org Chem (2013) 0.76

Synthetic Approaches for the Preparation of Phosphoramidate Prodrugs of 2'-Deoxypseudoisocytidine. ChemistryOpen (2017) 0.75

Novel synthetic route to the C-nucleoside, 2-deoxy benzamide riboside. Bioorg Med Chem Lett (2012) 0.75

Expanding a fluorescent RNA alphabet: synthesis, photophysics and utility of isothiazole-derived purine nucleoside surrogates. Chem Sci (2017) 0.75

Diastereoselective, Zinc-Catalyzed Alkynylation of α-Bromo Oxocarbenium Ions. Org Lett (2015) 0.75

Stereoselective C-glycosidations with achiral and enantioenriched allenylsilanes. Org Lett (2010) 0.75

Efficient synthesis of fluorescent alkynyl C-nucleosides via Sonogashira coupling for the preparation of DNA-based polyfluorophores. Org Biomol Chem (2016) 0.75

Articles by these authors

(truncated to the top 100)

Human DNA polymerase alpha uses a combination of positive and negative selectivity to polymerize purine dNTPs with high fidelity. Biochemistry (2007) 1.18

Asymmetric allylic substitution catalyzed by C1-symmetrical complexes of molybdenum: structural requirements of the ligand and the stereochemical course of the reaction. Chemistry (2006) 1.11

Modular and practical synthesis of 6-substituted pyridin-3-yl C-nucleosides. J Org Chem (2007) 0.97

Remote chiral induction in the organocatalytic hydrosilylation of aromatic ketones and ketimines. Angew Chem Int Ed Engl (2006) 0.96

New modular and efficient approach to 6-substituted pyridin-2-yl C-nucleosides. J Org Chem (2006) 0.88

Herpes simplex virus-1 DNA primase: a remarkably inaccurate yet selective polymerase. Biochemistry (2009) 0.88

An efficient method for the construction of functionalized DNA bearing amino acid groups through cross-coupling reactions of nucleoside triphosphates followed by primer extension or PCR. Chemistry (2007) 0.86

Synthesis of aldehyde-linked nucleotides and DNA and their bioconjugations with lysine and peptides through reductive amination. Chemistry (2012) 0.86

Direct polymerase synthesis of reactive aldehyde-functionalized DNA and its conjugation and staining with hydrazines. Angew Chem Int Ed Engl (2010) 0.85

Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyltrichlorosilanes: the role of arene-arene interactions. Angew Chem Int Ed Engl (2003) 0.85

On the selective N-methylation of BOC-protected amino acids. J Org Chem (2009) 0.85

Molybdenum(II)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics. J Org Chem (1999) 0.85

General and modular synthesis of isomeric 5-substituted pyridin-2-yl and 6-substituted pyridin-3-yl C-ribonucleosides bearing diverse alkyl, aryl, hetaryl, amino, carbamoyl, and hydroxy groups. J Org Chem (2011) 0.85

Optimization of the pyridyl nucleobase scaffold for polymerase recognition and unnatural base pair replication. Chembiochem (2008) 0.84

Aminophenyl- and nitrophenyl-labeled nucleoside triphosphates: synthesis, enzymatic incorporation, and electrochemical detection. Angew Chem Int Ed Engl (2008) 0.84

Synthesis of alpha-amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases. J Am Chem Soc (2003) 0.84

Synthesis and significant cytostatic activity of 7-hetaryl-7-deazaadenosines. J Med Chem (2011) 0.84

Vicinal amino alcohols as organocatalysts in asymmetric cross-aldol reaction of ketones: application in the synthesis of convolutamydine A. Org Lett (2007) 0.83

Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines. Org Biomol Chem (2006) 0.83

Direct C-H arylation of purines: development of methodology and its use in regioselective synthesis of 2,6,8-trisubstituted purines. Org Lett (2006) 0.82

Synthesis of enantiomerically pure (purin-6-yl)phenylalanines and their nucleosides, a novel type of purine-amino acid conjugates. J Org Chem (2005) 0.82

Synthesis of C-aryldeoxyribosides by [2 + 2 + 2]-cyclotrimerization catalyzed by Rh, Ni, Co, and Ru complexes. Org Lett (2006) 0.81

Mechanisms by which human DNA primase chooses to polymerize a nucleoside triphosphate. Biochemistry (2010) 0.81

6-(Het)aryl-7-deazapurine ribonucleosides as novel potent cytostatic agents. J Med Chem (2010) 0.81

A general and efficient synthesis of pyridin-2-yl C-ribonucleosides bearing diverse alkyl, aryl, amino, and carbamoyl groups in position 6. J Org Chem (2010) 0.81

B family DNA polymerases asymmetrically recognize pyrimidines and purines. Biochemistry (2011) 0.81

Furan-oxidation-triggered inducible DNA cross-linking: acyclic versus cyclic furan-containing building blocks--on the benefit of restoring the cyclic sugar backbone. Chemistry (2011) 0.81

Ferrocenylethynyl derivatives of nucleoside triphosphates: synthesis, incorporation, electrochemistry, and bioanalytical applications. Chemistry (2007) 0.80

Cleavage of adenine-modified functionalized DNA by type II restriction endonucleases. Nucleic Acids Res (2009) 0.80

Synthesis and photophysical properties of 7-deaza-2'-deoxyadenosines bearing bipyridine ligands and their Ru(II)-complexes in position 7. Org Biomol Chem (2008) 0.80

Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane. Org Lett (2004) 0.79

Synthesis of substituted 6-cyclopropylpurine bases and nucleosides by cross-coupling reactions or cyclopropanations. Org Biomol Chem (2008) 0.79

Nucleobase protection strategy for gene cloning and expression. Chembiochem (2013) 0.79

Modular synthesis of 1-α- and 1-β-(indol-2-yl)-2'-deoxyribose C-nucleosides. Org Biomol Chem (2011) 0.79

Transient and switchable (triethylsilyl)ethynyl protection of DNA against cleavage by restriction endonucleases. Angew Chem Int Ed Engl (2011) 0.79

Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides. Bioorg Med Chem (2007) 0.79

Synthesis, cytostatic, antimicrobial, and anti-HCV activity of 6-substituted 7-(het)aryl-7-deazapurine ribonucleosides. J Med Chem (2014) 0.79

Polymerase synthesis of DNA labelled with benzylidene cyanoacetamide-based fluorescent molecular rotors: fluorescent light-up probes for DNA-binding proteins. Chem Commun (Camb) (2015) 0.79

Molybdenum(II)- and Tungsten(II)-Catalyzed Allylic Substitution. J Org Chem (1999) 0.79

GFP-like fluorophores as DNA labels for studying DNA-protein interactions. J Org Chem (2012) 0.79

Cleavage of functionalized DNA containing 5-modified pyrimidines by type II restriction endonucleases. Chembiochem (2011) 0.79

Tail-labelling of DNA probes using modified deoxynucleotide triphosphates and terminal deoxynucleotidyl transferase. Application in electrochemical DNA hybridization and protein-DNA binding assays. Org Biomol Chem (2011) 0.78

CycloSal-phosphate pronucleotides of cytostatic 6-(Het)aryl-7-deazapurine ribonucleosides: Synthesis, cytostatic activity, and inhibition of adenosine kinases. ChemMedChem (2010) 0.78

Synthesis of enantiopure 1-arylprop-2-en-1-ols and their tert-butyl carbonates. J Org Chem (2008) 0.78

Preparation of short cytosine-modified oligonucleotides by nicking enzyme amplification reaction. Chem Commun (Camb) (2012) 0.78

Vinylsulfonamide and acrylamide modification of DNA for cross-linking with proteins. Angew Chem Int Ed Engl (2013) 0.78

Asymmetric reduction of imines with trichlorosilane, catalyzed by sigamide, an amino acid-derived formamide: scope and limitations. J Org Chem (2009) 0.78

Preparation of highly substituted 6-arylpurine ribonucleosides by Ni-catalyzed cyclotrimerization. Scope of the reaction. J Org Chem (2006) 0.78

Synthesis of new chiral 2,2'-bipyridine ligands and their application in copper-catalyzed asymmetric allylic oxidation and cyclopropanation. J Org Chem (2003) 0.78

Polymer-supported organocatalysts: asymmetric reduction of imines with trichlorosilane catalyzed by an amino acid-derived formamide anchored to a polymer. J Org Chem (2008) 0.78

Weak intra- and intermolecular interactions in a binaphthol imine: an experimental charge-density study on (+/-)-8'-benzhydrylideneamino-1,1'-binaphthyl-2-ol. Acta Crystallogr B (2009) 0.78

Soluble polymer-supported organocatalysts: asymmetric reduction of imines with trichlorosilane catalyzed by an amino acid derived formamide anchored to a soluble polymer. Chemistry (2009) 0.78

Exceptional thermodynamic stability of DNA duplexes modified by nonpolar base analogues is due to increased stacking interactions and favorable solvation: Correlated ab initio calculations and molecular dynamics simulations. Chemistry (2006) 0.78

Regioselective direct C-H arylations of protected uracils. Synthesis of 5- and 6-aryluracil bases. J Org Chem (2011) 0.78

Chiral 2,2'-bipyridine-type N-monoxides as organocatalysts in the enantioselective allylation of aldehydes with allyltrichlorosilane. Org Lett (2002) 0.78

Bodipy-labeled nucleoside triphosphates for polymerase synthesis of fluorescent DNA. Bioconjug Chem (2014) 0.77

Polymerase synthesis of DNAs bearing vinyl groups in the major groove and their cleavage by restriction endonucleases. Chembiochem (2014) 0.77

Organocatalysis with a fluorous tag: asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides. J Org Chem (2007) 0.77

7-Aryl-7-deazaadenine 2'-deoxyribonucleoside triphosphates (dNTPs): better substrates for DNA polymerases than dATP in competitive incorporations. Angew Chem Int Ed Engl (2014) 0.77

Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3beta-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality. J Org Chem (1996) 0.77

Analysis of stereochemical convergence in asymmetric pd-catalysed allylic alkylation reactions complicated by halide and memory effects. Chemistry (2002) 0.77

Organocatalysts immobilised onto gold nanoparticles: application in the asymmetric reduction of imines with trichlorosilane. Org Biomol Chem (2009) 0.77

Facile and efficient synthesis of 6-(hydroxymethyl)purines. Org Lett (2004) 0.77

The first synthesis and cytostatic activity of novel 6-(fluoromethyl)purine bases and nucleosides. Org Biomol Chem (2005) 0.77

Enantioselective Baeyer-Villiger oxidation catalyzed by palladium(II) complexes with chiral P,N-ligands. J Org Chem (2008) 0.77

2,8'-disubstituted-1,1'-binaphthyls: a new pattern in chiral ligands. Chemistry (2002) 0.77

Enantioselective and catalytic method for alpha-crotylation of aldehydes with a kinetic self-refinement of stereochemistry. Chemistry (2009) 0.77

Synthesis of 2,6-disubstituted pyridin-3-yl C-2'-deoxyribonucleosides through chemoselective transformations of bromo-chloropyridine C-nucleosides. Org Biomol Chem (2013) 0.77

Structural basis for inhibition of mycobacterial and human adenosine kinase by 7-substituted 7-(Het)aryl-7-deazaadenine ribonucleosides. J Med Chem (2014) 0.77

Phosphoramidate pronucleotides of cytostatic 6-aryl-7-deazapurine ribonucleosides. Bioorg Med Chem (2010) 0.77

Synthesis and photophysical properties of biaryl-substituted nucleos(t)ides. Polymerase synthesis of DNA probes bearing solvatochromic and pH-sensitive dual fluorescent and 19F NMR labels. J Org Chem (2011) 0.77

Synthesis and antiviral activity of 4,6-disubstituted pyrimido[4,5-b]indole ribonucleosides. Bioorg Med Chem (2012) 0.77

Scope and limitations of the nicking enzyme amplification reaction for the synthesis of base-modified oligonucleotides and primers for PCR. Bioconjug Chem (2013) 0.76

Interpretation of substituent effects on 13C and 15N NMR chemical shifts in 6-substituted purines. Phys Chem Chem Phys (2011) 0.76

Benzofurazane as a new redox label for electrochemical detection of DNA: towards multipotential redox coding of DNA bases. Chemistry (2013) 0.76

Base-modified DNA labeled by [Ru(bpy)(3)](2+) and [Os(bpy)(3)](2+) complexes: construction by polymerase incorporation of modified nucleoside triphosphates, electrochemical and luminescent properties, and applications. Chemistry (2009) 0.76

Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA. Org Biomol Chem (2010) 0.76

Synthesis of 8-bromo-, 8-methyl- and 8-phenyl-dATP and their polymerase incorporation into DNA. Org Biomol Chem (2008) 0.76

Desymmetrization of cyclic meso-epoxides with silicon tetrachloride catalyzed by PINDOX, a chiral bipyridine mono-N-oxide. Org Lett (2009) 0.76

Fluorescence quenching in oligonucleotides containing 7-substituted 7-deazaguanine bases prepared by the nicking enzyme amplification reaction. Bioconjug Chem (2015) 0.76

Polymerase synthesis of photocaged DNA resistant against cleavage by restriction endonucleases. Angew Chem Int Ed Engl (2014) 0.76

Synthesis of 6,8,9-tri- and 2,6,8,9-tetrasubstituted purines by a combination of the Suzuki cross-coupling, N-arylation, and direct C-H arylation reactions. J Org Chem (2008) 0.76

Polymerase synthesis of oligonucleotides containing a single chemically modified nucleobase for site-specific redox labelling. Chem Commun (Camb) (2013) 0.76

The first direct C-H arylation of purine nucleosides. Chem Commun (Camb) (2007) 0.76

Direct C-H borylation and C-H arylation of pyrrolo[2,3-d]pyrimidines: synthesis of 6,8-disubstituted 7-deazapurines. Org Biomol Chem (2009) 0.76

Anthraquinone as a redox label for DNA: synthesis, enzymatic incorporation, and electrochemistry of anthraquinone-modified nucleosides, nucleotides, and DNA. Chemistry (2011) 0.76

Alkylsulfanylphenyl derivatives of cytosine and 7-deazaadenine nucleosides, nucleotides and nucleoside triphosphates: synthesis, polymerase incorporation to DNA and electrochemical study. Chemistry (2011) 0.76

Synthesis of acetylene linked double-nucleobase nucleos(t)ide building blocks and polymerase construction of DNA containing cytosines in the major groove. J Org Chem (2011) 0.76

Synthesis of 2'-deoxyadenosine nucleosides bearing bipyridine-type ligands and their Ru-complexes in position 8 through cross-coupling reactions. Org Biomol Chem (2007) 0.75

Theoretical study of the stability of the DNA duplexes modified by a series of hydrophobic base analogues. Chemistry (2009) 0.75

Synthesis of nucleosides and dNTPs bearing oligopyridine ligands linked through an octadiyne tether, their incorporation into DNA and complexation with transition metal cations. Org Biomol Chem (2013) 0.75

Enantioselective synthesis of 1,2-diarylaziridines by the organocatalytic reductive amination of alpha-chloroketones. Angew Chem Int Ed Engl (2007) 0.75

Direct C-H sulfenylation of purines and deazapurines. Org Biomol Chem (2013) 0.75

Aqueous Heck cross-coupling preparation of acrylate-modified nucleotides and nucleoside triphosphates for polymerase synthesis of acrylate-labeled DNA. J Org Chem (2013) 0.75

Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation. Org Biomol Chem (2005) 0.75

New Lewis-basic N-oxides as chiral organocatalysts in asymmetric allylation of aldehydes. J Org Chem (2003) 0.75

Chiral recognition in solution and the gas phase. Experimental and theoretical studies of aromatic D- and L-amino acid-Cu(II)-chiragen complexes. J Mass Spectrom (2004) 0.75

METHOX: a new pyridine N-oxide organocatalyst for the asymmetric allylation of aldehydes with allyltrichlorosilanes. Org Lett (2005) 0.75

On the mechanism of asymmetric allylation of aldehydes with allyltrichlorosilanes catalyzed by QUINOX, a chiral isoquinoline N-oxide. J Am Chem Soc (2008) 0.75

Synthesis and biological activity of benzo-fused 7-deazaadenosine analogues. 5- and 6-substituted 4-amino- or 4-alkylpyrimido[4,5-b]indole ribonucleosides. Bioorg Med Chem (2013) 0.75