C-Nucleosides: Synthetic Strategies and Biological Applications

Genetical Implications of the Structure of Deoxyribonucleic Acid

WATSON, J. D., & CRICK, F. H. C. (1953) · Nature · doi:10.1038/171964b0 · Cited by 2,197

Iron-Catalyzed Reactions in Organic Synthesis

Bolm, C., Legros, J., Le Paih, J., & Zani, L. (2004) · Chemical Reviews · doi:10.1021/cr040664h · Cited by 2,148

MercuryII-Mediated Formation of Thymine−HgII−Thymine Base Pairs in DNA Duplexes

Miyake, Y., Togashi, H., Tashiro, M., Yamaguchi, H., Oda, S., Kudo, M., Tanaka, Y., Kondo, Y., Sawa, R., Fujimoto, T., et al. (2006) · Journal of the American Chemical Society · doi:10.1021/ja056354d · Cited by 1,079

Synthetic biology

Benner, S. A., & Sismour, A. M. (2005) · Nature Reviews Genetics · doi:10.1038/nrg1637 · Cited by 834

Enzymatic incorporation of a new base pair into DNA and RNA extends the genetic alphabet

Piccirilli, J. A., Benner, S. A., Krauch, T., Moroney, S. E., & Benner, S. A. (1990) · Nature · doi:10.1038/343033a0 · Cited by 638

New rules of selectivity: allylic alkylations catalyzed by palladium

Trost, B. M. (1980) · Accounts of Chemical Research · doi:10.1021/ar50155a001 · Cited by 635

DNA–Metal Base Pairs

Clever, G. H., Kaul, C., & Carell, T. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200701185 · Cited by 611

A Discrete Self-Assembled Metal Array in Artificial DNA

Tanaka, K., Tengeiji, A., Kato, T., Toyama, N., & Shionoya, M. (2003) · Science · doi:10.1126/science.1080587 · Cited by 565

Hydrogen Bonding, Base Stacking, and Steric Effects in DNA Replication

Kool, E. T. (2001) · Annual Review of Biophysics and Biomolecular Structure · doi:10.1146/annurev.biophys.30.1.1 · Cited by 505

Pseudouridine, a Carbon-Carbon Linked Ribonucleoside in Ribonucleic Acids: Isolation, Structure, and Chemical Characteristics

Cohn, W. E. (1960) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)69432-3 · Cited by 407

Stabilization of RNA stacking by pseudouridine

Davis, D. R. (1995) · Nucleic Acids Research · doi:10.1093/nar/23.24.5020 · Cited by 399

New general synthetic methods involving π-allylpalladium complexes as intermediates and neutral reaction conditions

Tsuji, J. (1986) · Tetrahedron · doi:10.1016/s0040-4020(01)87277-x · Cited by 398

Understanding Nucleic Acids Using Synthetic Chemistry

Benner, S. A. (2004) · Accounts of Chemical Research · doi:10.1021/ar040004z · Cited by 379

Enzymatic incorporation of a new base pair into DNA and RNA

Switzer, C., Moroney, S. E., & Benner, S. A. (1989) · Journal of the American Chemical Society · doi:10.1021/ja00203a067 · Cited by 360

Active Site Tightness and Substrate Fit in DNA Replication

Kool, E. T. (2002) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.71.110601.135453 · Cited by 350

Replacing the Nucleobases in DNA with Designer Molecules

Kool, E. T. (2002) · Accounts of Chemical Research · doi:10.1021/ar000183u · Cited by 345

A Novel Copper-Mediated DNA Base Pair

Meggers, E., Holland, P. L., Tolman, W. B., Romesberg, F. E., & Schultz, P. G. (2000) · Journal of the American Chemical Society · doi:10.1021/ja0025806 · Cited by 344

A comparison of potential molecular wires as components for molecular electronics

Robertson, N., & McGowan, C. A. (2003) · Chemical Society Reviews · doi:10.1039/b206919a · Cited by 337

Programmable self-assembly of metal ions inside artificial DNA duplexes

Tanaka, K. G., Clever, G. H., Takezawa, Y., Yamada, Y., Kaul, C., Shionoya, M., & Carell, T. (2006) · Nature Nanotechnology · doi:10.1038/nnano.2006.141 · Cited by 328

Mimicking the Structure and Function of DNA: Insights into DNA Stability and Replication

Kool, E. T., Morales, J. C., & Guckian, K. M. (2000) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(20000317)39:6<990::aid-anie990>3.0.co;2-0 · Cited by 321

Difluorotoluene, a Nonpolar Isostere for Thymine, Codes Specifically and Efficiently for Adenine in DNA Replication

Moran, S., Ren, R. X.-F., Rumney, & Kool, E. T. (1997) · Journal of the American Chemical Society · doi:10.1021/ja963718g · Cited by 317

A thymidine triphosphate shape analog lacking Watson–Crick pairing ability is replicated with high sequence selectivity

Moran, S., Ren, R. X.-F., & Kool, E. T. (1997) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.94.20.10506 · Cited by 310

A Simple Glycol Nucleic Acid

Zhang, L., Peritz, A., & Meggers, E. (2005) · Journal of the American Chemical Society · doi:10.1021/ja042564z · Cited by 308

An unnatural base pair for incorporating amino acid analogs into proteins

Hirao, I., Ohtsuki, T., Fujiwara, T., Mitsui, T., Yokogawa, T., Okuni, T., Nakayama, H., Takio, K., Yabuki, T., Kigawa, T., et al. (2002) · Nature Biotechnology · doi:10.1038/nbt0202-177 · Cited by 283

Ribosome-mediated incorporation of a non-standard amino acid into a peptide through expansion of the genetic code

Bain, J. D., Switzer, C., Chamberlin, R., & Benner, S. A. (1992) · Nature · doi:10.1038/356537a0 · Cited by 280

Beyond A, C, G and T: augmenting nature’s alphabet

Henry, A. A., & Romesberg, F. E. (2003) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2003.10.011 · Cited by 276

NUCLEOSIDES, NUCLEOTIDES & NUCLEIC ACIDS

Новопашина, Д. С., Ryabinin, V. A., Venyaminova, A. G., Sinyakov, A. N., Perrouault, L., Brunet, E., Giovannangeli, C., & Boutorine, A. S. (2004) · Cited by 272

Hydrophobic, Non-Hydrogen-Bonding Bases and Base Pairs in DNA

Schweitzer, B. A., & Kool, E. T. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00112a001 · Cited by 261

Enzymic recognition of the base pair between isocytidine and isoguanosine

Switzer, C. Y., Moroney, S. E., & Benner, S. A. (1993) · Biochemistry · doi:10.1021/bi00090a027 · Cited by 253

An unnatural hydrophobic base pair system: site-specific incorporation of nucleotide analogs into DNA and RNA

Hirao, I., Kimoto, M., Mitsui, T., Fujiwara, T., Kawai, R., Sato, A., Harada, Y., & Yokoyama, S. (2006) · Nature Methods · doi:10.1038/nmeth915 · Cited by 252

Structure of a Copper-Mediated Base Pair in DNA

Atwell, S., Meggers, E., Spraggon, G., et al. (2001) · Journal of the American Chemical Society · doi:10.1021/ja011822e · Cited by 250

One-Third-the-Sites Transition-State Inhibitors for Purine Nucleoside Phosphorylase

Miles, R. W., Tyler, P. C., Furneaux, R. H., Bagdassarian, C. K., & Schramm, V. L. (1998) · Biochemistry · doi:10.1021/bi980658d · Cited by 246

A specific partner for abasic damage in DNA

Matray, T. J., & Kool, E. T. (1999) · Nature · doi:10.1038/21453 · Cited by 236

A Four-Base Paired Genetic Helix with Expanded Size

Liu, H., Gao, J., Lynch, S. R., Saito, Y. D., Maynard, L., & Kool, E. T. (2003) · Science · doi:10.1126/science.1088334 · Cited by 227

Pseudouridine Synthases: Four Families of Enzymes Containing a Putative Uridine-Binding Motif Also Conserved in dUTPases and dCTP Deaminases

Koonin, E. V. (1996) · Nucleic Acids Research · doi:10.1093/nar/24.12.2411 · Cited by 224

Efficient Incorporation of a Copper Hydroxypyridone Base Pair in DNA

Tanaka, K., Tengeiji, A., Kato, T., et al. (2002) · Journal of the American Chemical Society · doi:10.1021/ja027175o · Cited by 211

Expanding the genetic code

Wang, L., & Schultz, P. G. (2002) · Chemical Communications · doi:10.1039/b108185n · Cited by 207

Formation of Silver(I)-Mediated DNA Duplex and Triplex through an Alternative Base Pair of Pyridine Nucleobases

Tanaka, K., Yamada, Y., & Shionoya, M. (2002) · Journal of the American Chemical Society · doi:10.1021/ja020510o · Cited by 205

Naphthalene, Phenanthrene, and Pyrene as DNA Base Analogues: Synthesis, Structure, and Fluorescence in DNA

Ren, R. X.-F., Chaudhuri, N. C., Paris, P. L., Rumney, & Kool, E. T. (1996) · Journal of the American Chemical Society · doi:10.1021/ja9612763 · Cited by 200

Artificially expanded genetic information system: a new base pair with an alternative hydrogen bonding pattern

Yang, Z., Hutter, D., Sheng, P., Sismour, A. M., & Benner, S. A. (2006) · Nucleic Acids Research · doi:10.1093/nar/gkl633 · Cited by 196

Immucillin H, a powerful transition-state analog inhibitor of purine nucleoside phosphorylase, selectively inhibits human T lymphocytes

Kicska, G. A., Long, L., Hörig, H., Fairchild, C., Tyler, P. C., Furneaux, R. H., Schramm, V. L., & Kaufman, H. L. (2001) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.071050798 · Cited by 192

Transition State Structure of Purine Nucleoside Phosphorylase and Principles of Atomic Motion in Enzymatic Catalysis,

Fedorov, A., Shi, W., Kicska, G., Fedorov, E., Tyler, P. C., Furneaux, R. H., Hanson, J. C., Gainsford, G. J., Larese, J. Z., Schramm, V. L., et al. (2001) · Biochemistry · doi:10.1021/bi002499f · Cited by 190

Design, Synthesis, and Antiviral Activity of Certain 2,5,6-Trihalo-1-(.beta.-D-ribofuranosyl)benzimidazoles

Townsend, L. B., Devivar, R. V., Turk, S. R., Nassiri, M. R., & Drach, J. C. (1995) · Journal of Medicinal Chemistry · doi:10.1021/jm00020a025 · Cited by 186

Minor Groove Interactions between Polymerase and DNA: More Essential to Replication than Watson−Crick Hydrogen Bonds?

Morales, J. C., & Kool, E. T. (1999) · Journal of the American Chemical Society · doi:10.1021/ja983502+ · Cited by 183

Aromatic Nonpolar Nucleosides as Hydrophobic Isosteres of Pyrimidines and Purine Nucleosides

Schweitzer, B. A., & Kool, E. T. (1994) · The Journal of Organic Chemistry · doi:10.1021/jo00103a013 · Cited by 172

Discovery, Characterization, and Optimization of an Unnatural Base Pair for Expansion of the Genetic Alphabet

Leconte, A. M., Hwang, G. T., Matsuda, S., Capek, P., Hari, Y., & Romesberg, F. E. (2008) · Journal of the American Chemical Society · doi:10.1021/ja078223d · Cited by 169

Broad-spectrum antiviral activity of 2-beta-D-ribofuranosylselenazole-4-carboxamide, a new antiviral agent

Kirsi, J. J., North, J. A., McKernan, P. A., Murray, B. K., Canonico, P. G., Huggins, J. W., Srivastava, P. C., & Robins, R. K. (1983) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.24.3.353 · Cited by 163

Efforts toward the Expansion of the Genetic Alphabet: Information Storage and Replication with Unnatural Hydrophobic Base Pairs

Ogawa, A. K., Wu, Y., McMinn, D. L., Liu, J., Schultz, P. G., & Romesberg, F. E. (2000) · Journal of the American Chemical Society · doi:10.1021/ja9940064 · Cited by 162

5-Ribosyl uracil, a carbon-carbon ribofuranosyl nucleoside in ribonucleic acids

Cohn, W. E. (1959) · Biochimica et Biophysica Acta · doi:10.1016/0006-3002(59)90644-4 · Cited by 161

Nucleobase Pairing in Expanded Watson-Crick-like Genetic Information Systems

Geyer, C. R., Battersby, T. R., & Benner, S. A. (2003) · Structure · doi:10.1016/j.str.2003.11.008 · Cited by 159

Synthesis and antitumor activity of 2-.beta.-D-ribofuranosylselenazole-4-carboxamide and related derivatives

Srivastava, P. C., & Robins, R. K. (1983) · Journal of Medicinal Chemistry · doi:10.1021/jm00357a024 · Cited by 157

The 2.0 A structure of human hypoxanthine-guanine phosphoribosyltransferase in complex with a transition-state analog inhibitor.

Schramm, V. L., Almo, S. C., Shi, W., Li, C. M., Tyler, P. C., Furneaux, R. H., & Grubmeyer, C. T. (1999) · Nature Structural Biology · doi:10.1038/9376 · Cited by 157

Solution structure of a DNA duplex containing a replicable difluorotoluene–adenine pair

Guckian, K. M., Krugh, T. R., & Kool, E. T. (1998) · Nature Structural Biology · doi:10.1038/2930 · Cited by 156

Unnatural base pair systems for DNA/RNA-based biotechnology

Hirao, I. (2006) · Current Opinion in Chemical Biology · doi:10.1016/j.cbpa.2006.09.021 · Cited by 150

The use of thymidine analogs to improve the replication of an extra DNA base pair: a synthetic biological system

Sismour, A. M. (2005) · Nucleic Acids Research · doi:10.1093/nar/gki873 · Cited by 147

Toward a New Genetic System with Expanded Dimensions: Size-Expanded Analogues of Deoxyadenosine and Thymidine

Liu, H., Gao, J., Maynard-Smith, L. A., Saito, Y. D., & Kool, E. T. (2004) · Journal of the American Chemical Society · doi:10.1021/ja038384r · Cited by 142

A Review: Synthesis of ArylC-Glycosides Via the Heck Coupling Reaction

Wellington, K. W., & Benner, S. A. (2006) · Nucleosides Nucleotides & Nucleic Acids · doi:10.1080/15257770600917013 · Cited by 130

Recognition by viral and cellular DNA polymerases of nucleosides bearing bases with nonstandard hydrogen bonding patterns.

Horlacher, J., Hottiger, M. O., Podust, V. N., Hübscher, U., & Benner, S. A. (1995) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.92.14.6329 · Cited by 124

Site-specific enzymic incorporation of an unnatural base, N6-(6-aminohexyl)isoguanosine, into RNA

Tor, Y., & Dervan, P. B. (1993) · Journal of the American Chemical Society · doi:10.1021/ja00064a007 · Cited by 120

Optimization of an Unnatural Base Pair toward Natural-Like Replication

Seo, Y. J., Hwang, G. T., Ordoukhanian, P. T., & Romesberg, F. E. (2009) · Journal of the American Chemical Society · doi:10.1021/ja807853m · Cited by 120

Transcription of an Expanded Genetic Alphabet

Seo, Y. J., Matsuda, S., & Romesberg, F. E. (2009) · Journal of the American Chemical Society · doi:10.1021/ja9006996 · Cited by 117

Polyfluorophores on a DNA Backbone: A Multicolor Set of Labels Excited at One Wavelength

Teo, Y. N., Wilson, J. N., & Kool, E. T. (2009) · Journal of the American Chemical Society · doi:10.1021/ja805502k · Cited by 116

Efforts toward Expansion of the Genetic Alphabet: Optimization of Interbase Hydrophobic Interactions

Wu, Y., Ogawa, A. K., Berger, M., McMinn, D. L., Schultz, P. G., & Romesberg, F. E. (2000) · Journal of the American Chemical Society · doi:10.1021/ja0009931 · Cited by 116

Probing the active site tightness of DNA polymerase in subangstrom increments

Kim, T. W., Delaney, J. C., Essigmann, J. M., & Kool, E. T. (2005) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0505113102 · Cited by 116

Investigation of Overhauser effects between pseudouridine and water protons in RNA helices

Newby, M. I., & Greenbaum, N. L. (2002) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.202477199 · Cited by 111

New Base Pairing Motifs. The Synthesis and Thermal Stability of Oligodeoxynucleotides Containing Imidazopyridopyrimidine Nucleosides with the Ability to Form Four Hydrogen Bonds

Minakawa, N., Kojima, N., Hikishima, S., Sasaki, T., Kiyosue, A., Atsumi, N., Ueno, Y., & Matsuda, A. (2003) · Journal of the American Chemical Society · doi:10.1021/ja0347686 · Cited by 110

Expanded-Size Bases in Naturally Sized DNA: Evaluation of Steric Effects in Watson−Crick Pairing

Gao, J., Liu, H., & Kool, E. T. (2004) · Journal of the American Chemical Society · doi:10.1021/ja048499a · Cited by 109

Metal–Salen‐Base‐Pair Complexes Inside DNA: Complexation Overrides Sequence Information

Clever, G. H., Söltl, Y., Burks, H. E., Spahl, W., & Carell, T. (2006) · Chemistry - A European Journal · doi:10.1002/chem.200600558 · Cited by 108

The difluorotoluene debate—a decade later

Kool, E. T., & Sintim, H. O. (2006) · Chemical Communications · doi:10.1039/b605414e · Cited by 98

PCR amplification of DNA containing non-standard base pairs by variants of reverse transcriptase from Human Immunodeficiency Virus-1

Sismour, A. M. (2004) · Nucleic Acids Research · doi:10.1093/nar/gkh241 · Cited by 96

Transition State Analogue Inhibitors of Purine Nucleoside Phosphorylase from Plasmodium falciparum

Kicska, G., Tyler, P. C., Evans, G. B., Furneaux, R. H., Kim, K., & Schramm, V. L. (2002) · Journal of Biological Chemistry · doi:10.1074/jbc.m105905200 · Cited by 95

Size-Expanded Analogues of dG and dC: Synthesis and Pairing Properties in DNA

Liu, H., Gao, J., & Kool, E. T. (2004) · The Journal of Organic Chemistry · doi:10.1021/jo048357z · Cited by 95

Synthetic biology: Act natural

Benner, S. A. (2003) · Nature · doi:10.1038/421118a · Cited by 95

Synthesis and cytotoxic activity of C-glycosidic nicotinamide riboside analogs

Krohn, K., Heins, H., & Wielckens, K. (1992) · Journal of Medicinal Chemistry · doi:10.1021/jm00081a012 · Cited by 93

Assembly of the Complete Eight‐Base Artificial Genetic Helix, xDNA, and Its Interaction with the Natural Genetic System

Gao, J., Liu, H., & Kool, E. T. (2005) · Angewandte Chemie International Edition · doi:10.1002/anie.200500069 · Cited by 89

Tautomerization Dynamics of a Model Base Pair in DNA

Abou‐Zied, O. K., Jimenez, R., & Romesberg, F. E. (2001) · Journal of the American Chemical Society · doi:10.1021/ja003647s · Cited by 86

Synthesis of 1,8‐Naphthyridine C‐Nucleosides and Their Base‐Pairing Properties in Oligodeoxynucleotides: Thermally Stable Naphthyridine:Imidazopyridopyrimidine Base‐Pairing Motifs

Hikishima, S., Minakawa, N., Kuramoto, K., Fujisawa, Y., Ogawa, M., & Matsuda, A. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200461857 · Cited by 81

Redesigning the Architecture of the Base Pair: Toward Biochemical and Biological Function of New Genetic Sets

Krueger, A. T., & Kool, E. T. (2009) · Chemistry & Biology · doi:10.1016/j.chembiol.2008.12.004 · Cited by 80

A pyrimidine-like nickel(ii) DNA base pair

Switzer, C., & Shin, D. (2005) · Chemical Communications · doi:10.1039/b415426f · Cited by 79

Nile Red Nucleoside: Design of a Solvatofluorochromic Nucleoside as an Indicator of Micropolarity around DNA

Okamoto, A., Tainaka, K., & Fujiwara, Y. (2006) · The Journal of Organic Chemistry · doi:10.1021/jo060168o · Cited by 77

Synthesis, Structure, and Antiproliferative Activity of Selenophenfurin, an Inosine 5‘-Monophosphate Dehydrogenase Inhibitor Analogue of Selenazofurin

Franchetti, P., Cappellacci, L., Sheikha, G. A., et al. (1997) · Journal of Medicinal Chemistry · doi:10.1021/jm960864o · Cited by 77

Hydrogen bonding in DNA—a return to the status quo

Evans, T. A., & Seddon, K. R. (1997) · Chemical Communications · doi:10.1039/a705239a · Cited by 77

Integrity of duplex structures without hydrogen bonding: DNA with pyrene paired at abasic sites

Smirnov, S. L. (2002) · Nucleic Acids Research · doi:10.1093/nar/gkf688 · Cited by 75

Asymmetric Allylic Substitution Catalyzed by C1‐Symmetrical Complexes of Molybdenum: Structural Requirements of the Ligand and the Stereochemical Course of the Reaction

Malkov, A. V., Gouriou, L., Lloyd‐Jones, G. C., Starý, I., Langer, V., Spoor, P., Vinader, V. M., & Kočovský, P. (2006) · Chemistry - A European Journal · doi:10.1002/chem.200501574 · Cited by 75

Varying DNA Base-Pair Size in Subangstrom Increments: Evidence for a Loose, Not Large, Active Site in Low-Fidelity Dpo4 Polymerase

Mizukami, S., Kim, T. W., Helquist, S. A., & Kool, E. T. (2006) · Biochemistry · doi:10.1021/bi051961z · Cited by 74

Stereodivergent Construction of Cyclic Ethers by a Regioselective and Enantiospecific Rhodium‐Catalyzed Allylic Etherification: Total Synthesis of Gaur Acid

Evans, P. A., Leahy, D. K., Andrews, W. J., & Uraguchi, D. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200460612 · Cited by 74

Toward a Designed, Functioning Genetic System with Expanded-Size Base Pairs: Solution Structure of the Eight-Base xDNA Double Helix

Lynch, S. R., Liu, H., Gao, J., & Kool, E. T. (2006) · Journal of the American Chemical Society · doi:10.1021/ja065606n · Cited by 73

A Diazirine-Based Nucleoside Analogue for Efficient DNA Interstrand Photocross-Linking

Qiu, Z., Lu, L., Jian, X., & He, C. (2008) · Journal of the American Chemical Society · doi:10.1021/ja805445j · Cited by 73

Artificial DNA Made Exclusively of Nonnatural C-Nucleosides with Four Types of Nonnatural Bases

Doi, Y., Chiba, J., Morikawa, T., & Inoûye, M. (2008) · Journal of the American Chemical Society · doi:10.1021/ja801058h · Cited by 71

Optimization of Unnatural Base Pair Packing for Polymerase Recognition

Matsuda, S., Henry, A. A., & Romesberg, F. E. (2006) · Journal of the American Chemical Society · doi:10.1021/ja057575m · Cited by 68

The Effect of Minor-Groove Hydrogen-Bond Acceptors and Donors on the Stability and Replication of Four Unnatural Base Pairs

Matsuda, S., Henry, A. A., Schultz, P. G., & Romesberg, F. E. (2003) · Journal of the American Chemical Society · doi:10.1021/ja034099w · Cited by 68

Minor Groove Hydrogen Bonds and the Replication of Unnatural Base Pairs

Matsuda, S., Leconte, A. M., & Romesberg, F. E. (2007) · Journal of the American Chemical Society · doi:10.1021/ja068282b · Cited by 68

Oligodeoxyfluorosides: strong sequence dependence of fluorescence emission

Wilson, J. N., Gao, J., & Kool, E. T. (2007) · Tetrahedron · doi:10.1016/j.tet.2006.07.113 · Cited by 66

Cofactor Mimics as Selective Inhibitors of NAD-dependent Inosine Monophospate Dehydrogenase (IMPDH) - the Major Therapeutic Target

Pankiewicz, K. W., Patterson, S., Black, P. L., et al. (2004) · Current Medicinal Chemistry · doi:10.2174/0929867043455648 · Cited by 61

Functional Evidence for a Small and Rigid Active Site in a High Fidelity DNA Polymerase

Kim, T. W., Brieba, L. G., Ellenberger, T., & Kool, E. T. (2005) · Journal of Biological Chemistry · doi:10.1074/jbc.m510744200 · Cited by 60

Substituent effects on the pairing and polymerase recognition of simple unnatural base pairs

Hwang, G. T., & Romesberg, F. E. (2006) · Nucleic Acids Research · doi:10.1093/nar/gkl049 · Cited by 60

Synthesis and Antiviral Evaluation of Trisubstituted Indole N-Nucleosides as Analogues of 2,5,6-Trichloro-1-(β- d -ribofuranosyl)benzimidazole (TCRB)

Chen, J. J., Wei, Y., Drach, J. C., et al. (2000) · Journal of Medicinal Chemistry · doi:10.1021/jm990320x · Cited by 58

Efficient Replication Bypass of Size‐Expanded DNA Base Pairs in Bacterial Cells

Delaney, J. C., Gao, J., Liu, H., Shrivastav, N., Essigmann, J. M., & Kool, E. T. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200805683 · Cited by 58

An Efficient Unnatural Base Pair for a Base-Pair-Expanded Transcription System

Mitsui, T., Kimoto, M., Harada, Y., Yokoyama, S., & Hirao, I. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0425280 · Cited by 57

Synthesis of 6-(2-thienyl)purine nucleoside derivatives that form unnatural base pairs with pyridin-2-one nucleosides

Fujiwara, T., Kimoto, M., Sugiyama, H., Hirao, I., & Yokoyama, S. (2001) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(01)00415-2 · Cited by 56

2‐Phenanthrenyl–DNA: Synthesis, Pairing, and Fluorescence Properties

Grigorenko, N. A., & Leumann, C. J. (2008) · Chemistry - A European Journal · doi:10.1002/chem.200801135 · Cited by 54

Nicotinamide Adenine Dinucleotide Based Therapeutics

Pankiewicz, K. W., Chen, L., Petrelli, R., Felczak, K., Gao, G., Bonnac, L. F., Yu, J., & Bennett, E. (2008) · Current Medicinal Chemistry · doi:10.2174/092986708783885282 · Cited by 53

Facile Polymerization of dNTPs Bearing Unnatural Base Analogues by DNA Polymerase α and Klenow Fragment (DNA Polymerase I)

Chiaramonte, M., Moore, C. L., Kincaid, K., & Kuchta, R. D. (2003) · Biochemistry · doi:10.1021/bi034763l · Cited by 52

A Direct Route to 3‐( D ‐Ribofuranosyl)pyridine Nucleosides

Piccirilli, J. A., Krauch, T., MacPherson, L. J., & Benner, S. A. (1991) · Helvetica Chimica Acta · doi:10.1002/hlca.19910740217 · Cited by 52

The Use of Nonnatural Nucleotides to Probe the Contributions of Shape Complementarity and π-Electron Surface Area during DNA Polymerization

Zhang, X., Lee, I., & Berdis, A. J. (2005) · Biochemistry · doi:10.1021/bi050585f · Cited by 51

8-Aza-immucillins as Transition-State Analogue Inhibitors of Purine Nucleoside Phosphorylase and Nucleoside Hydrolases

Evans, G. B., Furneaux, R. H., Gainsford, G. J., Hanson, J. C., Kicska, G., Sauve, A. A., Schramm, V. L., & Tyler, P. C. (2002) · Journal of Medicinal Chemistry · doi:10.1021/jm0203332 · Cited by 51

Stability and Polymerase Recognition of Pyridine Nucleobase Analogues: Role of Minor‐Groove H‐Bond Acceptors

Kim, Y., Leconte, A. M., Hari, Y., et al. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200602579 · Cited by 51

Selective Recognition of Unnatural Imidazopyridopyrimidine:Naphthyridine Base Pairs Consisting of Four Hydrogen Bonds by the Klenow Fragment

Minakawa, N., Ogata, S., Takahashi, M. M., & Matsuda, A. (2009) · Journal of the American Chemical Society · doi:10.1021/ja807391g · Cited by 49

Importance of Hydrogen Bonding for Efficiency and Specificity of the Human Mitochondrial DNA Polymerase

Lee, H. R., Helquist, S. A., Kool, E. T., & Johnson, K. A. (2007) · Journal of Biological Chemistry · doi:10.1074/jbc.m705007200 · Cited by 49

Pseudouridines in rRNA helix 69 play a role in loop stacking interactions

Desaulniers, J., Chang, Y., Aduri, R., Abeysirigunawardena, S. C., SantaLucia, J., & Chow, C. S. (2008) · Organic & Biomolecular Chemistry · doi:10.1039/b812731j · Cited by 48

Synthesis of 3-(2-deoxy-β-d-ribofuranosyl)pyridin-2-one and 2-amino-6-(N,N-dimethylamino)-9-(2-deoxy-β-d-ribofuranosyl)purine derivatives for an unnatural base pair

Ishikawa, M., Hirao, I., & Yokoyama, S. (2000) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)00520-7 · Cited by 48

A metallo base-pair incorporating a terpyridyl-like motif: bipyridyl-pyrimidinone·Ag(i)·4-pyridine

Shin, D., & Switzer, C. (2007) · Chemical Communications · doi:10.1039/b709291a · Cited by 47

Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics

Coleman, R. S., Berg, M. A., & Murphy, C. J. (2007) · Tetrahedron · doi:10.1016/j.tet.2006.12.096 · Cited by 45

A C-nucleotide base pair: methylpseudouridine-directed incorporation of formycin triphosphate into RNA catalyzed by T7 RNA polymerase

Piccirilli, J. A., Moroney, S. E., & Benner, S. A. (1991) · Biochemistry · doi:10.1021/bi00106a037 · Cited by 45

Hydrophobicity, Shape, and π-Electron Contributions during Translesion DNA Synthesis

Zhang, X., Lee, I., Zhou, X., & Berdis, A. J. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0546830 · Cited by 44

Dihydropyridine C-glycoconjugates by organocatalytic Hantzsch cyclocondensation. Stereoselective synthesis of α-threofuranose C-nucleoside enantiomers

Ducatti, D. R. B., Massi, A., Noseda, M. D., Duarte, M. E. R., & Dondoni, A. (2009) · Organic & Biomolecular Chemistry · doi:10.1039/b900422j · Cited by 43

Synthesis and Antiviral Evaluation of a Mutagenic and Non-Hydrogen Bonding Ribonucleoside Analogue: 1-β- d -Ribofuranosyl-3-nitropyrrole

Harki, D. A., Graci, J. D., Korneeva, V. S., Ghosh, S., Hong, Z., Cameron, C. E., & Peterson, B. R. (2002) · Biochemistry · doi:10.1021/bi026120w · Cited by 42

Rational Design of an Unnatural Base Pair with Increased Kinetic Selectivity

Ogawa, A. K., Wu, Y., Berger, M., Schultz, P. G., & Romesberg, F. E. (2000) · Journal of the American Chemical Society · doi:10.1021/ja001450u · Cited by 41

Synthesis and tautomeric equilibrium of 6-amino-5-benzyl-3-methylpyrazin-2-one. An acceptor-donor-donor nucleoside base analog

Voegel, J. J., von Krosigk, U., & Benner, S. A. (1993) · The Journal of Organic Chemistry · doi:10.1021/jo00078a038 · Cited by 40

The Chemistry of C-Nucleosides

Watanabe, K. A. (1994) · Springer eBooks · doi:10.1007/978-1-4757-9667-4_5 · Cited by 40

Tiazofurin metabolism in human lymphoblastoid cells: evidence for phosphorylation by adenosine kinase and 5'-nucleotidase.

Fridland, A., Connelly, M., & Robbins, T. J. (1986) · PubMed · Cited by 38

Human DNA Polymerase α Uses a Combination of Positive and Negative Selectivity To Polymerize Purine dNTPs with High Fidelity

Beckman, J. W., Kincaid, K., Hocek, M., Spratt, T. E., Engels, J. W., Cosstick, R., & Kuchta, R. D. (2006) · Biochemistry · doi:10.1021/bi061243s · Cited by 38

Difluorotoluene, a thymine isostere, does not hydrogen bond after all

Wang, X., & Houk, K. N. (1998) · Chemical Communications · doi:10.1039/a807425i · Cited by 36

An unnatural hydrophobic base, 4-propynylpyrrole-2-carbaldehyde, as an efficient pairing partner of 9-methylimidazo[(4,5)- b ]pyridine

Mitsui, T., Kimoto, M., Sato, A., Yokoyama, S., & Hirao, I. (2003) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2003.09.059 · Cited by 36

Deoxyadenosine and Thymidine Bases Held Proximal and Distal by Means of a Covalently-Linked Dimensional Analogue of dA·dT: Intramolecular vs Intermolecular Hydrogen Bonding1

Bhat, B., Leonard, N. J., Robinson, H. H., & Wang, A. H. ‐. (1996) · Journal of the American Chemical Society · doi:10.1021/ja9618255 · Cited by 34

An HIV Reverse Transcriptase-Selective Nucleoside Chain Terminator

Fraley, A. W., Chen, D., Johnson, K. A., & McLaughlin, L. W. (2002) · Journal of the American Chemical Society · doi:10.1021/ja020639y · Cited by 31

Synthetic Incorporation of Metal Complexes into Nucleic Acids and Peptides Directed toward Functionalized Molecules

Shionoya, M., & Tanaka, K. G. (2000) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.73.1945 · Cited by 28

2′-Deoxy-1-methylpseudocytidine, a stable analog of 2′-deoxy-5-methylisocytidine

Kim, H., Leal, N. A., & Benner, S. A. (2009) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2009.03.047 · Cited by 28

Fluorous Base‐Pairing Effects in a DNA Polymerase Active Site

Lai, J. S., & Kool, E. T. (2005) · Chemistry - A European Journal · doi:10.1002/chem.200401151 · Cited by 25

Dimetalation of Pyrazines. A One-Pot Synthesis of Multisubstituted Pyrazine C-Nucleosides

Liu, W., Wise, D. S., & Townsend, L. B. (2001) · The Journal of Organic Chemistry · doi:10.1021/jo001555f · Cited by 24

Synthesis of 5-acetyl-2-aminopyrrole C-deoxyribonucleoside

Oda, H., Hanami, T., Iwashita, T., Kojima, M., Itoh, M., & Hayashizaki, Y. (2007) · Tetrahedron · doi:10.1016/j.tet.2007.09.082 · Cited by 24

Expanding the Genetic Alphabet: Pyrazine Nucleosides That Support a DonorDonorAcceptor Hydrogen‐Bonding Pattern

von Krosigk, U., & Benner, S. A. (2004) · Helvetica Chimica Acta · doi:10.1002/hlca.200490120 · Cited by 22

Probing the Active Site Steric Flexibility of HIV-1 Reverse Transcriptase: Different Constraints for DNA- versus RNA-Templated Synthesis

Silverman, A. P., Garforth, S., Prasad, V. R., & Kool, E. T. (2008) · Biochemistry · doi:10.1021/bi702427y · Cited by 19

RNA Probes of Steric Effects in Active Sites: High Flexibility of HIV-1 Reverse Transcriptase

Silverman, A. P., & Kool, E. T. (2007) · Journal of the American Chemical Society · doi:10.1021/ja072791b · Cited by 12

Phosphorothioation of Oligonucleotides Strongly Influences the Inhibition of Bacterial (M.HhaI) and Human (Dnmt1) DNA Methyltransferases

Warncke, S., Gégout, A., & Carell, T. (2009) · ChemBioChem · doi:10.1002/cbic.200800798 · Cited by 5

Use of Nucleoside Analogues to Probe Biochemical Processes

McLaughlin, L. W., Wilson, M., & Ha, S. B. (1999) · Elsevier eBooks · doi:10.1016/b978-0-08-091283-7.00062-x · Cited by 5

The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold

Seley-Radtke, K. L., & Yates, M. K. (2018) · Antiviral Research · doi:10.1016/j.antiviral.2018.04.004 · Cited by 543

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

Bokor, É., Kun, S., Goyard, D., Tóth, M., Praly, J.-P., Vidal, S., & Somsák, L. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00475 · Cited by 304

High Fidelity Enzyme‐Free Primer Extension with an Ethynylpyridone Thymidine Analog

Han, J., Kervio, E., & Richert, C. (2021) · Chemistry – A European Journal · doi:10.1002/chem.202102996 · Cited by 7