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Relevant bibliographies by topics / 2'-deoxy purine nucleosides

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Academic literature on the topic '2'-deoxy purine nucleosides'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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Journal articles on the topic "2'-deoxy purine nucleosides"

1

Ren, Hang, Haoyun An, Paul J. Hatala, William C. Stevens, Jingchao Tao, and Baicheng He. "Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides." Beilstein Journal of Organic Chemistry 11 (December 9, 2015): 2509–20. http://dx.doi.org/10.3762/bjoc.11.272.

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A unified synthetic strategy accessing novel 3'-fluorinated purine nucleoside derivatives and their biological evaluation were achieved. Novel 3’-fluorinated analogues were constructed from a common 3’-deoxy-3’-fluororibofuranose intermediate. Employing Suzuki and Stille cross-coupling reactions, fifteen 3’-fluororibose purine nucleosides 1–15 and eight 3’-fluororibose 2-chloro/2-aminopurine nucleosides 16–23 with various substituents at position 6 of the purine ring were efficiently synthesized. Furthermore, 3’-fluorine analogs of natural products nebularine and 6-methylpurine riboside were constructed via our convergent synthetic strategy. Synthesized nucleosides were tested against HT116 (colon cancer) and 143B (osteosarcoma cancer) tumor cell lines. We have demonstrated 3’-fluorine purine nucleoside analogues display potent tumor cell growth inhibition activity at sub- or low micromolar concentration.

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2

Robins, Morris J., Ruiming Zou, Fritz Hansske, and Stanislaw F. Wnuk. "Synthesis of sugar-modified 2,6-diaminopurine and guanine nucleosides from guanosine via transformations of 2-aminoadenosine and enzymatic deamination with adenosine deaminase." Canadian Journal of Chemistry 75, no. 6 (June 1, 1997): 762–67. http://dx.doi.org/10.1139/v97-092.

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Treatment of 2,6-diaminopurine riboside (2-aminoadenosine) with α-acetoxyisobutyryl bromide in acetonitrile gave mixtures of the trans 2′,3′-bromohydrin acetates 2. Treatment of 2 with zinc–copper couple effected reductive elimination, and deprotection gave 2,6-diamino-9-(2,3-dideoxy-β-D-erythro-pent-2-enofuranosyl)purine (3a). Treatment of 2 with Dowex 1 × 2 (OH−) resin in methanol gave the 2′,3′-anhydro derivative 4. Stannyl radical-mediated hydrogenolysis of 2 and deprotection gave the 2′-deoxy 6a and 3′-deoxy 7a nucleosides. Treatment of the 3′,5′-O-(tetraisopropyldisiloxanyl) derivative (5a) with trifluoromethanesulfonyl chloride – 4-(dimethylamino)pyridine gave 2′-triflate 5c. Displacement with lithium azide–dimethylformamide and deprotection gave the arabino 2′-azido derivative 8a, which was reduced to give 2,6-diamino-9-(2-amino-2-deoxy-β-D-arabinofuranosyl)purine (8b). Sugar-modified 2,6-diaminopurine nucleosides were treated with adenosine deaminase to give the corresponding guanine analogues. Keywords: adenosine deaminase, 2,6-diaminopurine nucleosides, deoxygenation, guanine nucleosides, nucleosides.

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3

Karwowski, Bolesław. "Consequence of hydrogen atom abstraction from 5’-hydroxyl group of 2’-deoxyadenosine. Theoretical quantum mechanics study." Open Chemistry 6, no. 3 (September 1, 2008): 450–55. http://dx.doi.org/10.2478/s11532-008-0038-z.

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AbstractReactive oxygen species (ROS) may generate different nucleoside/nucleotide radicals in a cell environment. In this study, the possibility of cyclic-2’-deoxyadenosines formation by a rearrangement of their free radicals was investigated. It seems that for cyclic-nucleosides formation, adoption of an O4’-exo conformation by the sugar moiety is necessary. However, this is the energetically unfavoured form of the 2-deoxyribose ring. Moreover, the creation of a O5’, C8 bond in purine deoxy-nucleosides/nucleotides leads to the termination of the DNA elongation process.

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4

Fateev, Ilja V., Konstantin V. Antonov, Irina D. Konstantinova, Tatyana I. Muravyova, Frank Seela, Roman S. Esipov, Anatoly I. Miroshnikov, and Igor A. Mikhailopulo. "The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases." Beilstein Journal of Organic Chemistry 10 (July 22, 2014): 1657–69. http://dx.doi.org/10.3762/bjoc.10.173.

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Two approaches to the synthesis of 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (1, clofarabine) were studied. The first approach consists in the chemical synthesis of 2-deoxy-2-fluoro-α-D-arabinofuranose-1-phosphate (12a, 2FAra-1P) via three step conversion of 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (9) into the phosphate 12a without isolation of intermediary products. Condensation of 12a with 2-chloroadenine catalyzed by the recombinant E. coli purine nucleoside phosphorylase (PNP) resulted in the formation of clofarabine in 67% yield. The reaction was also studied with a number of purine bases (2-aminoadenine and hypoxanthine), their analogues (5-aza-7-deazaguanine and 8-aza-7-deazahypoxanthine) and thymine. The results were compared with those of a similar reaction with α-D-arabinofuranose-1-phosphate (13a, Ara-1P). Differences of the reactivity of various substrates were analyzed by ab initio calculations in terms of the electronic structure (natural purines vs analogues) and stereochemical features (2FAra-1P vs Ara-1P) of the studied compounds to determine the substrate recognition by E. coli nucleoside phosphorylases. The second approach starts with the cascade one-pot enzymatic transformation of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a, followed by its condensation with 2-chloroadenine thereby affording clofarabine in ca. 48% yield in 24 h. The following recombinant E. coli enzymes catalyze the sequential conversion of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a: ribokinase (2-deoxy-2-fluoro-D-arabinofuranose-5-phosphate), phosphopentomutase (PPN; no 1,6-diphosphates of D-hexoses as co-factors required) (12a), and finally PNP. The substrate activities of D-arabinose, D-ribose and D-xylose in the similar cascade syntheses of the relevant 2-chloroadenine nucleosides were studied and compared with the activities of 2-deoxy-2-fluoro-D-arabinose. As expected, D-ribose exhibited the best substrate activity [90% yield of 2-chloroadenosine (8) in 30 min], D-arabinose reached an equilibrium at a concentration of ca. 1:1 of a starting base and the formed 2-chloro-9-(β-D-arabinofuranosyl)adenine (6) in 45 min, the formation of 2-chloro-9-(β-D-xylofuranosyl)adenine (7) proceeded very slowly attaining ca. 8% yield in 48 h.

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5

Ting, Jing-Wen, Min-Feng Wu, Chih-Tung Tsai, Ching-Chun Lin, Ing-Cherng Guo, and Chi-Yao Chang. "Identification and characterization of a novel gene of grouper iridovirus encoding a purine nucleoside phosphorylase." Journal of General Virology 85, no. 10 (October 1, 2004): 2883–92. http://dx.doi.org/10.1099/vir.0.80249-0.

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Purine nucleoside phosphorylase (PNP) is a key enzyme in the purine salvage pathway. It catalyses the reversible phosphorolysis of purine (2′-deoxy)ribonucleosides to free bases and (2′-deoxy)ribose 1-phosphates. Here, a novel piscine viral PNP gene that was identified from grouper iridovirus (GIV), a causative agent of an epizootic fish disease, is reported. This putative GIV PNP gene encodes a protein of 285 aa with a predicted molecular mass of 30 332 Da and shows high similarity to the human PNP gene. Northern and Western blot analyses of GIV-infected grouper kidney (GK) cells revealed that PNP expression increased in cells with time from 6 h post-infection. Immunocytochemistry localized GIV PNP in the cytoplasm of GIV-infected host cells. PNP–EGFP fusion protein was also observed in the cytoplasm of PNP–EGFP reporter construct-transfected GK and HeLa cells. From HPLC analysis, the recombinant GIV PNP protein was shown to catalyse the reversible phosphorolysis of purine nucleosides and could accept guanosine, inosine and adenosine as substrates. In conclusion, this is the first report of a viral PNP with enzymic activity.

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6

Mikhailopulo, Igor, Alexandra Denisova, Yulia Tokunova, Ilja Fateev, Alexandra Breslav, Vladimir Leonov, Elena Dorofeeva, et al. "The Chemoenzymatic Synthesis of 2-Chloro- and 2-Fluorocordycepins." Synthesis 49, no. 21 (July 20, 2017): 4853–60. http://dx.doi.org/10.1055/s-0036-1590804.

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Two approaches to the chemoenzymatic synthesis of 2-fluorocordycepin and 2-chlorocordycepin were studied: (i) the use of 3′-deoxyadenosine (cordycepin) and 3′-deoxyinosine (3′dIno) as donors of 3-deoxy-d-ribofuranose in the transglycosylation of 2-fluoro- (2FAde) and 2-chloroadenine (2ClAde) catalyzed by the recombinant E. coli purine nucleoside phosphorylase (PNP), and (ii) the use of 2-fluoroadenosine and 3′-deoxyinosine as substrates of the cross-glycosylation and PNP as a biocatalyst. An efficient method for 3′-deoxyinosine synthesis starting from inosine was developed. However, the very poor solubility of 2ClAde and 2FAde is the limiting factor of the first approach. The second approach enables this problem to be overcome and it appears to be advantageous over the former approach from the viewpoint of practical synthesis of the title nucleosides. The 3-deoxy-α-d-ribofuranose-1-phosphate intermediary formed in the 3′dIno phosphorolysis by PNP was found to be the weak and marginal substrate of E. coli thymidine (TP) and uridine (UP) phosphorylases, respectively. Finally, one-pot cascade transformation of 3-deoxy-d-ribose in cordycepin in the presence of adenine and E. coli ribokinase, phosphopentomutase, and PNP was tested and cordycepin formation in ca. 3.4% yield was proved.

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7

Hronowski, Lucjan J. J., and Walter A. Szarek. "Regiospecific synthesis of cyclopentane analogs of (2′- and 3′-deoxy-threo-pentofuranosyl)-uracil and -2-thiouracil nucleosides." Canadian Journal of Chemistry 63, no. 10 (October 1, 1985): 2787–97. http://dx.doi.org/10.1139/v85-464.

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Aminohydroxycyclopentanemethanols are important precursors for the synthesis of cyclopentane analogs of purine and pyrimidine nucleosides. The regiospecific synthesis of two new aminohydroxycyclopentanemethanols, 17 and 22, is described. In these syntheses the desired configuration in the cyclopentane ring is obtained by opening the cis-acetoxy-1,3-cyclopentanedicarboxylic acid anhydride 3 with either ammonia or methanol. The attack by each nucleophile occurs at the carbonyl carbon farthest away from the acetoxy group to give a carbamoyl or an ester function at this position. Since the ester function is destined to become the hydroxymethyl substituent and the carbamoyl function the amino substituent, the type of nucleophile used to open the anhydride determines whether the 2-deoxy or the 3-deoxy isomer is obtained. Coupling of the aminohydroxycyclopentanemethanols with 3-ethoxypropenoyl isocyanate followed by cyclization of the acyl ureas in 2 N H2SO4 gave two new cyclopentane analogs of uracil nucleosides. Coupling of the aminohydroxycyclopentanemethanols with 3-ethoxypropenoyl isothiocyanate followed by cyclization of the acyl thioureas in 15 N aqueous ammonia gave two new cyclopentane analogs of 2-thiouracil nucleosides.

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8

Van Draanen, Nanine A., George A. Freeman, Steven A. Short, Robert Harvey, Robert Jansen, George Szczech, and George W. Koszalka. "Synthesis and Antiviral Activity of 2‘-Deoxy-4‘-thio Purine Nucleosides." Journal of Medicinal Chemistry 39, no. 2 (January 1996): 538–42. http://dx.doi.org/10.1021/jm950701k.

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9

Messini, Lea, Kamal N. Tiwari, John A. Montgomery, and John A. Secrist. "Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides." Nucleosides and Nucleotides 18, no. 4-5 (April 1999): 683–85. http://dx.doi.org/10.1080/15257779908041540.

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10

Yamada, K. "Practical synthesis of 2'-deoxy-2'-fluoroarabinofuranosyl purine nucleosides by chemo-emzymatic method." Nucleic Acids Symposium Series 48, no. 1 (November 1, 2004): 45–46. http://dx.doi.org/10.1093/nass/48.1.45.

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Dissertations / Theses on the topic "2'-deoxy purine nucleosides"

1

Zhong, Minghong. "N9 Alkylation and Glycosylation of Purines; A Practical Synthesis of 2-Chloro-2'-deoxyadenosine." Diss., CLICK HERE for online access, 2004. http://contentdm.lib.byu.edu/ETD/image/etd433.pdf.

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2

Fazio, Fabio. "Building blocks for 2-deoxy-L-nucleosides." [S.l. : s.n.], 2001. http://deposit.ddb.de/cgi-bin/dokserv?idn=963273434.

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3

Midtkandal, R. R. "A stereocontrolled method for the synthesis of D-and L-2 deoxy-C-nucleosides using an intramolecular Sakurai-type cyclisation reaction." Thesis, Queen's University Belfast, 2012. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.546333.

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4

Fazio, Fabio [Verfasser]. "Building blocks for 2-deoxy-L-nucleosides / by Fabio Fazio." 2001. http://d-nb.info/963273434/34.

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5

Smolka, Ondřej. "Syntéza analogů nukleosidů založených na derivátech 2-deoxy-2-fluor- a 3-deoxy-3-fluor-D-ribosy a pyrazinu." Master's thesis, 2020. http://www.nusl.cz/ntk/nusl-435858.

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This thesis deals with the synthesis of prodrugs based on analogs of nucleoside phosphonates derived from 6-fluoro-3-hydroxypyrazine-2-carboxamide (T-705) and 3- hydroxypyrazine-2-carboxamide (T-1105). T-705 and T-1105 act as inhibitors of an influenza RNA polymerase. Both compounds mimic naturally occurring nucleobases, so their fluorinated nucleoside phosphonates could also be biologically active. Derivatives of 2-deoxy-2-fluoro-D-ribose (2-FdR) were prepared in this work. Because of complications during the syntthesis of 3-deoxy-3-fluoro-D-ribose (3-FdR) derivatives, 5- deoxy-5-fluoro-D-xylose (5-FdX) derivatives were prepared instead. Deoxyfluorination was done after incorporation of suitable protecting groups followed by selective deprotection and phosphonate binding. Furthermore nucleosides were synthetised using silyl-Hilbert-Johnson method and their bis-POM derivattives were also prepared. Key words: favipiravir (T-705), T-1105, prodrugs, phosphonates, fluorinated nucleosides

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Book chapters on the topic "2'-deoxy purine nucleosides"

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Matsuda, Akira, Atsushi Azuma, Yuki Nakajima, Kenji Takenuki, Akihito Dan, Tomoharu Iino, Yuichi Yoshimura, Noriaki Minakawa, Motohiro Tanaka, and Takuma Sasaki. "Design of New Types of Antitumor Nucleosides: The Synthesis and Antitumor Activity of 2′-Deoxy-(2′-C-Substituted)Cytidines." In Nucleosides and Nucleotides as Antitumor and Antiviral Agents, 1–22. Boston, MA: Springer US, 1993. http://dx.doi.org/10.1007/978-1-4615-2824-1_1.

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2

Pankiewicz, Krzysztof W., and Kyoichi A. Watanabe. "A Synthesis of 2’-Fluoro- and 3’-Fluoro-Substituted Purine Nucleosides via a Direct Approach." In Nucleosides and Nucleotides as Antitumor and Antiviral Agents, 55–71. Boston, MA: Springer US, 1993. http://dx.doi.org/10.1007/978-1-4615-2824-1_3.

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3

Hirota, Kosaku, Yasunari Monguchi, and Hironao Sajki. "Synthesis of Purine Acyclonucleosides via Ribofuranose-Ring Cleavage of Purine Nucleosides by Diisobutylaluminum Hydride." In Recent Advances in Nucleosides: Chemistry and Chemotherapy, 57–70. Elsevier, 2002. http://dx.doi.org/10.1016/b978-044450951-2/50003-5.

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4

El Kouni, Mahmoud H. "Purine Metabolism in Parasites: Potential Targets for Chemotherapy." In Recent Advances in Nucleosides: Chemistry and Chemotherapy, 377–416. Elsevier, 2002. http://dx.doi.org/10.1016/b978-044450951-2/50013-8.

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5

CADET, JEAN, MAURICE BERGER, GARRY BUCHKO, and JEAN-LUC RAVANAT. "RADICAL OXIDATION PRODUCTS OF THE PURINE MOIETIES OF NUCLEOSIDES AND DNA." In Radiation Research: A Twentieth-century Perspective, 400. Elsevier, 1991. http://dx.doi.org/10.1016/b978-0-12-168561-4.50123-2.

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Conference papers on the topic "2'-deoxy purine nucleosides"

1

Hřebabecký, Hubert. "Synthesis of carba analogues of 2'-deoxy-4'-C-(hydroxymethyl)nucleosides." 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/css199902266.

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2

Panagopoulos, Dimitris, Antonio Salgado, and Thanasis Gimisis. "Preparation of 2'-deoxy nucleosides of cyanuric acid for their inclusion in DNA oligonucleotides." 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/css200507449.

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Reports on the topic "2'-deoxy purine nucleosides"

1

Nair, Vasu. Rare 2-Substituted Purine Nucleosides. Fort Belvoir, VA: Defense Technical Information Center, May 1989. http://dx.doi.org/10.21236/adb132700.

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2

Nair, Vasu. Rare 2-Substituted Purine Nucleosides. Fort Belvoir, VA: Defense Technical Information Center, October 1987. http://dx.doi.org/10.21236/adb119120.

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