Tautomerism provides a molecular explanation for the mutagenic properties of the anti-HIV nucleoside 5-aza-5,6-dihydro-2'-deoxycytidine

Tautomerism provides a molecular explanation for the mutagenic properties of the anti-HIV nucleoside 5-aza-5,6-dihydro-2'-deoxycytidine

Viral lethal mutagenesis is a strategy whereby the innate immune system or mutagenic pool nucleotides increase the error rate of viral replication above the error catastrophe limit. Lethal mutagenesis has been proposed as a mechanism for several antiviral compounds, including the drug candidate 5-az...

Full description

Bibliographic Details
Main Authors:	Li, Deyu, Fedeles, Bogdan I., Singh, Vipender, Peng, Chunte Sam, Silvestre, Katherine J., Simi, Allison K., Simpson, Jeffrey H., Essigmann, John M., Tokmakoff, Andrei
Other Authors:	Massachusetts Institute of Technology. Center for Environmental Health Sciences
Format:	Article
Language:	en_US
Published:	National Academy of Sciences (U.S.) 2015
Online Access:	http://hdl.handle.net/1721.1/93785 https://orcid.org/0000-0002-8241-4834 https://orcid.org/0000-0002-2196-5691

Similar Items

Role of tautomerism in RNA biochemistry
by: Singh, Vipender, et al.
Published: (2014)

Two-dimensional IR spectroscopy of the anti-HIV agent KP1212 reveals protonated and neutral tautomers that influence pH-dependent mutagenicity
by: Peng, Chunte, et al.
Published: (2015)

Intrinsic mutagenic properties of 5-chlorocytosine: A mechanistic connection between chronic inflammation and cancer
by: Fedeles, Bogdan I., et al.
Published: (2016)

Identification and characterization of microRNA candidates that are upregulated by 5-aza-2’-deoxycytidine treatment in hepatocellular carcinoma cells.
by: Leng, Charmaine Yong En.
Published: (2009)

Mutation of HIV-1 Genomes in a Clinical Population Treated with the Mutagenic Nucleoside KP1461
by: Mullins, James I., et al.
Published: (2011)

Direct Observation of Multiple Tautomers of Oxythiamine and their Recognition by the Thiamine Pyrophosphate Riboswitch
by: Singh, Vipender, et al.
Published: (2015)

Direct observation of ground-state lactam-lactim tautomerization using temperature-jump transient 2D IR spectroscopy
by: Peng, Chunte Sam, et al.
Published: (2014)

The AlkB Family of Fe(II)/α-Ketoglutarate-dependent Dioxygenases: Repairing Nucleic Acid Alkylation Damage and Beyond
by: Fedeles, Bogdan I., et al.
Published: (2015)

Two-dimensional infrared spectroscopy of nucleic acids : application to tautomerism and DNA aptamer unfolding dynamics
by: Peng, Chunte Sam
Published: (2014)

Red-to-black electrochromism of 4,9-dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-embedded conjugated polymers
by: Cho, Ching Mui, et al.
Published: (2016)

Spectroscopic analysis and synthesis of nucleoside analogs for lethal mutagenesis
by: Silvestre, Katherine J
Published: (2015)

An engineered cell line lacking OGG1 and MUTYH glycosylases implicates the accumulation of genomic 8-oxoguanine as the basis for paraquat mutagenicity
by: Tajai, Preechaya, et al.
Published: (2021)

4,5-Dihydro-3a, 5a-diazoniapyrene triiodidocuprate(I)
by: Wu, D., et al.
Published: (2011)

Poly[[aqua(μ5-1H-benzimidazole-5,6-dicarboxylato)(μ4-1H-benzimidazole-5,6-dicarboxylato)dibarium] 4.5-hydrate]
by: Zhang, Heng-Qiang, et al.
Published: (2011)

Oncometabolites D- and L-2-hydroxyglutarate Inhibit the AlkB Family DNA Repair Enzymes under Physiological Conditions
by: Chen, Fangyi, et al.
Published: (2018)

Oxidative DNA damage : mutagenic properties of 5-hydorxycytosine, 5-hydroxyuracil and uracil glycol in Eschericia coli
by: Kreutzer, Deborah A
Published: (2010)

3,5-Bis(4-bromophenyl)-1-phenyl-4,5-dihydro-1H-pyrazole
by: Samshuddin, S., et al.
Published: (2010)

Impact of DNA lesion repair, replication and formation on the mutational spectra of environmental carcinogens: Aflatoxin B1 as a case study
by: Fedeles, Bogdan I., et al.
Published: (2020)

5-Acetyl-3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one
by: Rida, M., et al.
Published: (2011)

1-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone
by: Abbas, A., et al.
Published: (2010)

Crystal structure of 5-(4-methoxyphenyl)- 3-(4-methylphenyl)-4,5-dihydro-1Hpyrazole- 1-carbaldehyde
by: Adam, Farook, et al.
Published: (2015)

The damaging November 2022 Mw 5.6 earthquake in West Java, Indonesia
by: Yun, S., et al.
Published: (2023)

X-ray, IR, NMR, UV-visible spectra and DFT analysis of 5-aryloxy-(1H)-tetrazoles, structure, conformation and tautomerism
by: Pesyan, Nader Noroozi, et al.
Published: (2014)

Computational study of uracil tautomeric forms in the ribosome : the case of uracil and 5-oxyacetic acid uracil in the first anticodon position of tRNA
by: Hartono, Yossa Dwi, et al.
Published: (2019)

Embedded singly diagonally implicit Runge-Kutta methods (4,5) in (5,6). For the integration of stiff systems of ODEs
by: Ismail, Fudziah, et al.
Published: (1998)

The Cyclisation of l-Aryl-2-Benzamidoalkan-l-Ols to 4,5-DihydroOxazoles or Isoquinolines
by: Md. Sharif, Atan, et al.
Published: (1990)

1-{5-[4-(Hexyloxy)phenyl]-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl}ethan one
by: Abbas, A., et al.
Published: (2010)

Crystal structure of 5-[4-(dimethylamino) phenyl]-3-(4-methylphenyl)-4,5- dihydro-1H-pyrazole-1-carbaldehyde
by: Adam, Farook, et al.
Published: (2016)

Catalytic regioselective acylation of unprotected nucleosides for quick access to COVID and other nucleoside prodrugs
by: Lv, Jie, et al.
Published: (2023)

Mechanism of Repair of Acrolein- and Malondialdehyde-Derived Exocyclic Guanine Adducts by the α-Ketoglutarate/Fe(II) Dioxygenase AlkB
by: Singh, Vipender, et al.
Published: (2015)

Investigating non-nucleoside inhibitors targeting the Zika virus non-structural protein 5 (NS5) RNA-dependent RNA polymerase (RdRp) domain
by: Zhang, Denzel Xugeng
Published: (2022)

2-[4-Acetyl-5-(biphenyl-4-yl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]phenyl acetate
by: Yehye, W.A., et al.
Published: (2010)

2- 4-Acetyl-5-(biphenyl-4-yl)-4,5-dihydro-1,3,4-oxadiazol-2-yl phenyl acetate
by: Ariffin, Azhar, et al.
Published: (2010)

1-[5-(2-Chlorophenyl)-3-(4-methylphenyl)-4,5-dihydro- 1H-pyrazol-1-yl]ethan-1-one
by: Adam, Farook, et al.
Published: (2016)

4-Methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one monohydrate
by: Saber, A., et al.
Published: (2010)

Synthesis of 3-(4’-nitrophenyl)-4,5-Dihydro Pyrazole-Based and Its In-vitro Antibacterial Test
by: Fauzi’ah, Lina, et al.
Published: (2022)

Synthesis of 3-(4’-nitrophenyl)-4,5-Dihydro Pyrazole-Based and Its In-vitro Antibacterial Test
by: Fauzi’ah, Lina, et al.
Published: (2022)

2-Chloro-6,6-dimethyl-5,6-dihydroindazolo[2,3-c]quinazoline
by: Boechat, N., et al.
Published: (2010)

Snapshots of radical enzyme catalysis : the crystal structures of biotin synthase and lysine 5,6-aminomutase
by: Berkovitch, Frederick, 1978-
Published: (2005)

Polarization Components in π0 Photoproduction at Photon Energies up to 5.6 GeV
by: Bertozzi, William, et al.
Published: (2012)