Modified DNA Bases: Probing Base‐Pair Recognition by Polymerases

Kool, Eric T.

doi:10.1002/9783527623112.ch3

Cited by 5 publications

(4 citation statements)

References 98 publications

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“…For many years, nucleoside analogs have been used as antiviral agents (Cihlar, Delaney, & Mackman, 2008; De Clercq & Li, 2016; Yates & Seley‐Radtke, 2019), antitumor agents (Jordheim, Durantel, Zoulim, & Dumontet, 2013; Secrist, Thottassery, & Parker, 2008; Shelton et al., 2016), and as research instruments for cellular processes (Kool, 2008; Kreutz & Micura, 2008; Lengeler & Weisz, 2006; Volkova, Chudinov, & Lapa, 2021). The only methods of obtaining nucleoside analogs are chemical or biotechnological synthesis (Merino, 2013; Mikhailopulo & Miroshnikov, 2010, 2011).…”

Section: Commentarymentioning

confidence: 99%

5‐Substituted 1,2,4‐Triazole‐3‐Carboxylates and 5‐Substituted Ribavirin Analogs Synthesis

et al. 2021

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Ribavirin analogs substituted at position 5 of the heterocyclic base are interesting for their biological activity. This protocol describes a synthetic route to several such ribavirin analogs with a wide range of substituents.© 2021 Wiley Periodicals LLC. Basic Protocol 1: Synthesis and purification of 5‐substituted ethyl 1,2,4‐triazole‐3‐carboxylates – synthetic precursors of nucleobases Basic Protocol 2: Synthesis and purification of protected 1,2,4‐triazole nucleoside analogs Basic Protocol 3: Synthesis and purification of 5‐substituted ribavirin analogs

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Section: Commentarymentioning

confidence: 99%

5‐Substituted 1,2,4‐Triazole‐3‐Carboxylates and 5‐Substituted Ribavirin Analogs Synthesis

et al. 2021

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“…Modified base pairs accepted by polymerases are essential for creation of new forms of xeno-DNA (Kool 2008). Initial efforts to expand the genetic code introduced the isoC-isoG pair (Piccirilli et al, 1990).…”

Section: Introductionmentioning

confidence: 99%

Pyridone-based nucleotide analogues accepted for DNA biosynthesis

Mikalkėnas¹,

Ravoitytė²,

Tauraitė³

et al. 2017

biologija

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Novel pyridone-based nucleotides were investigated for maintenance of DNA synthesis, carried on by representatives of different classes of polymerases. Five different nucleoside triphosphates of similar structure were addressed, demonstrating involvement in primer extension. The nucleotides containing 4-chloro-and 4-bromo-2-pyridone as a nucleobase were preferred by all DNA polymerases tested. These nucleotides were incorporated up to several instances in a row and unexpectedly failed to ensure DNA primer termination. Temporary polymerase stalling obeys kinetic constrain and is alleviated by availability of nucleotides readily acquired by the polymerase. Lack of inhibitory properties of 2-pyridone nucleobase confirms the processivity of DNA polymerases challenged by incorporated nucleotides.

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“…Continuous efforts in the development of new antiviral agents are a consequence of the urgent demand for new therapeutic agents in which improved biological activity against viruses is matched with low toxicity towards host cells. In this context, particular interest has been focused on the synthesis and the biological activity of nucleoside analogues, in which structural modifications of the heterocyclic bases and/or the sugar moiety of natural nucleosides have been performed [1,2,3,4,5,6,7,8,9,10,11,12,13]. A remarkable impulse for research on nucleoside analogues arose from the urgent need to find a therapeutic approach to combat human immunodeficiency virus (HIV) infections.…”

Section: Introductionmentioning

confidence: 99%

Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation

et al. 2014

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Abstract:Starting from enantiomeric pure 1-[(3S,5R)-and 1-[(3R,5S)-3-(hydroxymethyl)-2-methylisoxazolidin-5-yl]-5-methylpyrimidine-2,4(1H,3H)-diones (−)7a and (+)7b, obtained by lipase-catalyzed resolution, pure diethyl{[(3S,5R)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl}phosphonate (−)12a and diethyl{[(3R,5S)-2-methyl-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)isoxazolidin-3-yl]methyl} phosphonate (+)12b have been synthesized. The obtained compounds showed no cytotoxic activity versus the U937 cell line in comparison with AZT, and were poorly able to inhibit HIV infection in vitro.

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Modified DNA Bases: Probing Base‐Pair Recognition by Polymerases

Cited by 5 publications

References 98 publications

5‐Substituted 1,2,4‐Triazole‐3‐Carboxylates and 5‐Substituted Ribavirin Analogs Synthesis

5‐Substituted 1,2,4‐Triazole‐3‐Carboxylates and 5‐Substituted Ribavirin Analogs Synthesis

Pyridone-based nucleotide analogues accepted for DNA biosynthesis

Enantiomerically Pure Phosphonated Carbocyclic 2'-Oxa-3'-Azanucleosides: Synthesis and Biological Evaluation

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