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Relevant bibliographies by topics / Synthesis of nucleotide analogues

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Academic literature on the topic 'Synthesis of nucleotide analogues'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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Journal articles on the topic "Synthesis of nucleotide analogues"

1

Dutartre, Hélène, Cécile Bussetta, Joëlle Boretto, and Bruno Canard. "General Catalytic Deficiency of Hepatitis C Virus RNA Polymerase with an S282T Mutation and Mutually Exclusive Resistance towards 2′-Modified Nucleotide Analogues." Antimicrobial Agents and Chemotherapy 50, no. 12 (September 25, 2006): 4161–69. http://dx.doi.org/10.1128/aac.00433-06.

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ABSTRACT The hepatitis C virus (HCV) RNA-dependent RNA polymerase NS5B is an important target for antiviral therapies. NS5B is able to initiate viral RNA synthesis de novo and then switch to a fast and processive RNA elongation synthesis mode. The nucleotide analogue 2′-C-methyl CTP (2′-C-Me-CTP) is the active metabolite of NM283, a drug currently in clinical phase II trials. The resistance mutation S282T can be selected in HCV replicon studies. Likewise, 2′-O-Me nucleotides are active both against the purified polymerase and in replicon studies. We have determined the molecular mechanism by which the S282T mutation confers resistance to 2′-modified nucleotide analogues. 2′-C-Me-CTP is no longer incorporated during the initiation step of RNA synthesis and is discriminated 21-fold during RNA elongation by the NS5B S282T mutant. Strikingly, 2′-O-methyl CTP sensitivity does not change during initiation, but the analogue is no longer incorporated during elongation. This mutually exclusive resistance mechanism suggests not only that “2′-conformer” analogues target distinct steps in RNA synthesis but also that these analogues have interesting potential in combination therapies. In addition, the presence of the S282T mutation induces a general cost in terms of polymerase efficiency that may translate to decreased viral fitness: natural nucleotides become 5- to 20-fold less efficiently incorporated into RNA by the NS5B S282T mutant. As in the case for human immunodeficiency virus, our results might provide a mechanistic basis for the rational combination of drugs for low-fitness viruses.

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Nairne, R. James D., Lea Pickering, and Clifford L. Smith. "Synthesis of pyrrole carboxamide nucleotide triphosphates—putative labelled nucleotide analogues." Tetrahedron Letters 43, no. 12 (March 2002): 2289–91. http://dx.doi.org/10.1016/s0040-4039(02)00225-3.

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Chamberlain, Brian T., Thomas G. Upton, Boris A. Kashemirov, and Charles E. McKenna. "α-Azido Bisphosphonates: Synthesis and Nucleotide Analogues." Journal of Organic Chemistry 76, no. 12 (June 17, 2011): 5132–36. http://dx.doi.org/10.1021/jo200045a.

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Bordoni, Cinzia, Cecilia Maria Cima, Elisa Azzali, Gabriele Costantino, and Andrea Brancale. "Microwave-assisted organic synthesis of nucleoside ProTide analogues." RSC Advances 9, no. 35 (2019): 20113–17. http://dx.doi.org/10.1039/c9ra01754b.

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Scism, Robert A., Donald F. Stec, and Brian O. Bachmann. "Synthesis of Nucleotide Analogues by a Promiscuous Phosphoribosyltransferase." Organic Letters 9, no. 21 (October 2007): 4179–82. http://dx.doi.org/10.1021/ol7016802.

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Xu, Yunjian, Frank Schwede, Hans Wienk, Anders Tengholm, and Holger Rehmann. "A Membrane Permeable Prodrug of S223 for Selective Epac2 Activation in Living Cells." Cells 8, no. 12 (December 6, 2019): 1589. http://dx.doi.org/10.3390/cells8121589.

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Signalling by cyclic adenosine monophosphate (cAMP) occurs via various effector proteins, notably protein kinase A and the guanine nucleotide exchange factors Epac1 and Epac2. These proteins are activated by cAMP binding to conserved cyclic nucleotide binding domains. The specific roles of the effector proteins in various processes in different types of cells are still not well defined, but investigations have been facilitated by the development of cyclic nucleotide analogues with distinct selectivity profiles towards a single effector protein. A remaining challenge in the development of such analogues is the poor membrane permeability of nucleotides, which limits their applicability in intact living cells. Here, we report the synthesis and characterisation of S223-AM, a cAMP analogue designed as an acetoxymethyl ester prodrug to overcome limitations of permeability. Using total internal reflection imaging with various fluorescent reporters, we show that S223-AM selectively activates Epac2, but not Epac1 or protein kinase A, in intact insulin-secreting β-cells, and that this effect was associated with pronounced activation of the small G-protein Rap. A comparison of the effects of different cAMP analogues in pancreatic islet cells deficient in Epac1 and Epac2 demonstrates that cAMP-dependent Rap activity at the β-cell plasma membrane is exclusively dependent on Epac2. With its excellent selectivity and permeability properties, S223-AM should get broad utility in investigations of cAMP effector involvement in many different types of cells.

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Laux, Wolfgang HG, Stéphane Priet, Karine Alvarez, Suzanne Peyrottes, and Christian Périgaud. "Synthesis and substrate properties towards HIV-1 reverse transcriptase of new diphosphate analogues of 9-[(2-phosphonomethoxy)ethyl]adenine." Antiviral Chemistry and Chemotherapy 26 (January 2018): 204020661875763. http://dx.doi.org/10.1177/2040206618757636.

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Background The replacement of β,γ-pyrophosphate by β,γ-phosphonate moieties within the triphosphate chain of 5′-triphosphate nucleoside analogues was previously studied for various antiviral nucleoside analogues such as AZT and 2′,3′-dideoxynucleosides. Thus, it has been shown that these chemical modifications could preserve, in some cases, the terminating substrate properties of the triphosphate analogue for HIV-RT. Herein, we aimed to study such 5′-triphosphate mimics based on the scaffold of the well-known antiviral agent 9-[(2-phosphonomethoxy)ethyl]adenine (PMEA, Adefovir). Methods Synthesis involved coupling of a morpholidate derivative of PMEA with appropriate pyrophosphoryl analogues. The relative efficiencies of incorporation of the studied diphosphate phosphonates were measured using subtype B WT HIV-1 RT in an in vitro susceptibility assay, in comparison to the parent nucleotide analogue (PMEApp). Results Searching for nucleoside 5′-triphosphate mimics, we have synthesized and studied a series of diphosphate analogues of PMEA bearing non hydrolysable bonds between the and phosphorus atoms. We also examined their relative inhibitory capacity towards HIV-1 reverse transcriptase in comparison to the parent nucleotide analogue (PMEApp). Only one of them appeared as a weak inhibitor (IC50 = 403.0 ± 75.5 µM) and proved to be less effective than PMEApp (IC50 = 6.4 ± 0.8 µM). Conclusion PMEA diphosphoryl derivatives were designed as potential substrates and/or inhibitors of various viral polymerases. These modifications dramatically affect their ability to inhibit HIV-RT.

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Zhou, Ding, Irene M. Lagoja, Arthur Van Aerschot, and Piet Herdewijn. "Synthesis of Aminopropyl Phosphonate Nucleosides with Purine and Pyrimidine Bases." Collection of Czechoslovak Chemical Communications 71, no. 1 (2006): 15–34. http://dx.doi.org/10.1135/cccc20060015.

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The synthesis and antiviral evaluation of new acyclic phosphonate nucleosides related to HPMPC (Cidofovir) has been described. These aminopropyl phosphonate nucleosides 1-3 have an amino function within either the acyclic chain (series 2 and 3) or as substituent (series 1). Both purine and pyrimidine nucleotide analogues have been synthesized. In contrast to HPMPC the oxygen analogue of 2c, only a weak antiherpes virus activity could be demonstrated for 2b and 2c.

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9

Alexander, Petr, V. V. Krishnamurthy, and Ernest J. Prisbe. "Synthesis and Antiviral Activity of Pyranosylphosphonic Acid Nucleotide Analogues." Journal of Medicinal Chemistry 39, no. 6 (January 1996): 1321–30. http://dx.doi.org/10.1021/jm950788+.

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GI, H. J., Y. XIANG, R. F. SCHINAZI, and K. ZHAO. "ChemInform Abstract: Synthesis of Dihydroisoxazole Nucleoside and Nucleotide Analogues." ChemInform 28, no. 21 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199721232.

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Dissertations / Theses on the topic "Synthesis of nucleotide analogues"

1

Blunt, Caroline Jane. "Biological applications of nucleotide analogues." Thesis, University of Oxford, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.279832.

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Williams, David Mark. "The synthesis and studies of nucleotide analogues." Thesis, University of Liverpool, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.235527.

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Cormier, James. "The synthesis of nucleoside and silyl nucleotide analogues /." Thesis, McGill University, 1987. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=75458.

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A route to the synthesis of arabino and xylonucleosides is described. This route takes advantage of highly selective ribonucleoside hydroxyl protection procedures which have recently been developed. The route is straightforward and broadly applicable. It may be applied to both purine and pyrimidine nucleosides. Synthesis, deprotection, and characterisation of the target compounds are described. The work is compared to that of others in the field.
A novel class of oligonucleotide analogues is described. In this group, the phosphorus atom of the internucleotide link is replaced by silicon. The synthesis of both oligothymidine and oligo-2$ sp prime$-deoxyadenosine nucleotide analogues of this class is described. Various substituents at silicon are employed, and oligonucleotide analogs of up to six units long are synthesised, characterised and deprotected. The circular dichroism spectra of the deprotected hexamers is presented.

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Higson, Adrian Peter. "The synthesis of 3'-thionucleoside and nucleotide analogues." Thesis, University of Liverpool, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.240326.

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Scott, Gerard Kevin. "The synthesis of nucleotide analogues using the Michaelis-Arbuzov reaction." Thesis, University of Liverpool, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.240771.

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6

Kincaid, Karen Kristin. "Studies of nucleotide analogues: DNA polymerase fidelity and the solid-phase synthesis of nucleosides and nucleotides." Diss., Connect to online resource, 2006. http://gateway.proquest.com/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqdiss&rft_dat=xri:pqdiss:3219202.

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Coe, Diane Mary. "Synthesis of carbocyclic nucleoside and nucleotide analogues as potential antiviral agents." Thesis, University of Exeter, 1991. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.294036.

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Pal, Ayan. "Synthesis Of Nucleoside Analogues: Glycosylation, Rigid Nucleosides And Janus Wedge Derivatives." Thesis, Boston College, 2012. http://hdl.handle.net/2345/2750.

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Thesis advisor: Larry W. McLaughlin
Thesis advisor: Mary F. Roberts
Nucleic Acids are unique biopolymers capable of encoding and transferring genetic information from one generation to the next for every form of life. This fascinating property has made them the topic of intense research from a variety of aspects. Some researchers try to understand how life might have started. Some try to elucidate how the whole process works. Some try to use the properties of nucleic acids as a tool for various purposes. The continuous effort over more than a century explored a lot about the structures and functions of nucleic acids. There is a lot to be discovered yet. This work began with the design and development of a new class of nucleoside analogue with the goal to study their ability to bind nucleic acids. The ongoing research will establish their application as therapeutics and as biomolecular tools. Along the way significant effort went into preparing these analogues. New methodology was developed to address some of the unanswered synthetic problems of nucleoside chemistry
Thesis (PhD) — Boston College, 2012
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry

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9

Wang, Yikang. "Synthesis of some novel phospholipids, and nucleotide analogues, as potential chemotherapeutic agents and for DNA sequencing." Thesis, University of Southampton, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.295106.

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10

Löpfe, Michael Löpfe Michael. "Synthesis of carbon-analogues of 2,4-diaminopyrimidine and 2-oxo-4-aminopyrimidine homo-DNA nucleosides : Study of homo-DNA oligonucleotides containing carbon-analogues of the 2,4-diaminopyrimidine nucleotide /." [S.l.] : [s.n.], 2009. http://opac.nebis.ch/cgi-bin/showAbstract.pl?sys=000286574.

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Books on the topic "Synthesis of nucleotide analogues"

1

Shimizu, Shin-Ichiro. The synthesis of nucleoside and nucleotide analogues as potential antiviral agents. Birmingham: University of Birmingham, 1991.

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2

S, Bruzik K., and Stec W. J, eds. Biophosphates and their analogues: Synthesis, structure, metabolism, and activity : proceedings of the 2nd International Symposium on Phosphorus Chemistry Directed Towards Biology, Łodz, Poland, 8-12 September 1986. Amsterdam: Elsevier, 1987.

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3

Martin, John C., ed. Nucleotide Analogues as Antiviral Agents. Washington, DC: American Chemical Society, 1989. http://dx.doi.org/10.1021/bk-1989-0401.

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4

Hark, Richard R. Synthesis of ninhydrin analogues. [Philadelphia, Pa.]: [s.n.], 1996.

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5

Athmani, Salah. Synthesis of cytokinin analogues. Salford: University of Salford, 1991.

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6

Cook, Stuart. The synthesis of prostacyclin analogues. Norwich: University of East Anglia, 1985.

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7

Merino, Pedro, ed. Chemical Synthesis of Nucleoside Analogues. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118498088.

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8

Merino, Pedro. Chemical synthesis of nucleoside analogues. Hoboken, N.J: Wiley, 2013.

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9

Richardson, K. A. The synthesis of heterocyclic prostacyclin analogues. Norwich: University of East Anglia, 1985.

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10

O'Connell, Grace. The enzymatic synthesis of nucleoside analogues. [s.l.]: typescript, 1994.

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Book chapters on the topic "Synthesis of nucleotide analogues"

1

Marquez, Victor E. "Design, Synthesis, and Antiviral Activity of Nucleoside and Nucleotide Analogues." In ACS Symposium Series, 140–55. Washington, DC: American Chemical Society, 1989. http://dx.doi.org/10.1021/bk-1989-0401.ch010.

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2

Okello, Maurice, and Vasu Nair. "Methodologies for the Synthesis of Isomeric Nucleosides and Nucleotides of Antiviral Significance." In Chemical Synthesis of Nucleoside Analogues, 317–43. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118498088.ch8.

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3

Cusack, Noel J. "Synthesis of Adenosine and Adenine Nucleotide Analogs." In Methods Used in Adenosine Research, 3–20. Boston, MA: Springer US, 1985. http://dx.doi.org/10.1007/978-1-4684-4886-3_1.

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4

Lin, Tai-Shun, and Mao-Chin Liu. "Synthesis and Anticancer and Antiviral Activity of Certain Pyrimidine Nucleoside Analogues." In Nucleosides and Nucleotides as Antitumor and Antiviral Agents, 177–201. Boston, MA: Springer US, 1993. http://dx.doi.org/10.1007/978-1-4615-2824-1_10.

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Bronson, Joanne J., Ismail Ghazzouli, Michael J. M. Hitchcock, Robert R. Webb, Earl R. Kern, and John C. Martin. "Synthesis and Antiviral Activity of Nucleotide Analogues Bearing the (S)-(3-Hydroxy-2-phosphonylmethoxy)propyl Moiety Attached to Adenine, Guanine, and Cytosine." In ACS Symposium Series, 88–102. Washington, DC: American Chemical Society, 1989. http://dx.doi.org/10.1021/bk-1989-0401.ch006.

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6

Romeo, Roberto, Caterina Carnovale, Antonio Rescifina, and Maria Assunta Chiacchio. "Phosphonated Nucleoside Analogues." In Chemical Synthesis of Nucleoside Analogues, 163–208. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118498088.ch4.

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Boutureira, Omar, M. Isabel Matheu, Yolanda Díaz, and Sergio Castillón. "Synthesis ofC-Nucleosides." In Chemical Synthesis of Nucleoside Analogues, 263–316. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118498088.ch7.

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8

Zalkin, Howard. "De Novo Purine Nucleotide Synthesis." In Bacillus subtilis and Other Gram-Positive Bacteria, 335–41. Washington, DC, USA: ASM Press, 2014. http://dx.doi.org/10.1128/9781555818388.ch24.

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Switzer, Robert L., and Cheryl L. Quinn. "De Novo Pyrimidine Nucleotide Synthesis." In Bacillus subtilis and Other Gram-Positive Bacteria, 343–58. Washington, DC, USA: ASM Press, 2014. http://dx.doi.org/10.1128/9781555818388.ch25.

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Baddiley, J., and N. A. Hughes. "The Synthesis of Nucleotide Coenzymes." In Advances in Enzymology - and Related Areas of Molecular Biology, 157–203. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2006. http://dx.doi.org/10.1002/9780470122679.ch4.

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Conference papers on the topic "Synthesis of nucleotide analogues"

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Kers, Annika, Inger Kers, Jacek Stawinski, Jacek Cieślak, Jadwiga Jankowska, and Adam Kraszewski. "Developing synthetic methods for nucleotide analogues. A progress report." In XIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 1999. http://dx.doi.org/10.1135/css199902069.

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Hocková, Dana, Antonín Holý, and Milena Masojídková. "Synthesis of acyclic nucleotide analogues derived from 5-substituted 2,4-diamino-6-hydroxypyrimidines." In XIIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2002. http://dx.doi.org/10.1135/css200205326.

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Ivanov, Alexander V., Maxim V. Jasko, Yuri S. Skoblov, and Marina K. Kukhanova. "The synthesis of an acyclic nucleotide analogue, (E)-9-(3-phosphonylmethoxypropen-1-yl)adenine." In XIIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2002. http://dx.doi.org/10.1135/css200205043.

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Dabkowski, Wojciech, and Jan Michalski. "A novel approach to synthesis of nucleotides and their structural analogues via tricoordinate phosphorus reagents." In XIIIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2005. http://dx.doi.org/10.1135/css200507039.

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Lavén, Gaston, and Jacek Stawinski. "A new synthetic route to diastereomerically pure P-chiral nucleotide analogues, dinucleoside benzylphosphonates, via stereospecific Pd(0) catalyzed cross-coupling reaction." In XIVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810395.

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Janeba, Zlatko, and Antonín Holý. "Synthesis of 8-hydroxy and 8-mercapto derivatives of acyclic adenine nucleoside and nucleotide analogs. Alkylation of 8-substituted adenines." In XIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 1999. http://dx.doi.org/10.1135/css199902260.

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Murakami, Eisuke, and Adrian S. Ray. "Nucleoside/nucleotide analogues for HCV." In XVIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2014. http://dx.doi.org/10.1135/css201414035.

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Pohl, Radek, Dominik Rejman, Petr Kočalka, and Ivan Rosenberg. "Pyrrolidine nucleotide analogues – conformation study." In XIIIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2005. http://dx.doi.org/10.1135/css200507165.

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Pohl, Radek, Miloš Buděšínský, Dominik Rejman, Petr Kočalka, and Ivan Rosenberg. "Conformation of pyrrolidine ring in pyrrolidine nucleotide analogues." In XIVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810435.

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Kolodziej, Krystian, Adam Kraszewski, Jacek Stawinski, and Michal Sobkowski. "The loss of TEAH+ cation from certain nucleotide analogues." In XVIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2014. http://dx.doi.org/10.1135/css201414373.

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Reports on the topic "Synthesis of nucleotide analogues"

1

Schneller, Stewart W. Synthesis and Antiviral Evaluation of Pyrazofurin Analogues. Fort Belvoir, VA: Defense Technical Information Center, June 1991. http://dx.doi.org/10.21236/ada239014.

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Schneller, Stewart W. Synthesis and Antiviral Evaluation of Pyrazofurin Analogues. Fort Belvoir, VA: Defense Technical Information Center, June 1990. http://dx.doi.org/10.21236/ada227154.

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Su, Ning, Jerald S. Bradshaw, Paul B. Savage, Guoping Xue, Krzysztof E. Krakowiak, and Reed M. Izaft. Synthesis of Novel 8-Hydroxyquinoline-Containing Diaz-18-Crown-6 Ligands and Analogues. Fort Belvoir, VA: Defense Technical Information Center, November 1999. http://dx.doi.org/10.21236/ada370492.

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Jenkins, C. W., R. B. King, and I. Bresinska. Synthesis of Polystyrene-Supported Dithizone Analogues for Use as Chemical Sensors for Heavy Metals. Office of Scientific and Technical Information (OSTI), July 1998. http://dx.doi.org/10.2172/656434.

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Walker, Richard T. Synthesis of Nucleoside Analogues with Potential Antiviral Activity against Negative Strand RNA Virus Targets. Fort Belvoir, VA: Defense Technical Information Center, November 1989. http://dx.doi.org/10.21236/ada229411.

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