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

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Published: 4 June 2021

Last updated: 3 February 2022

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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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11

Il’icheva, Irina A., Konstantin M. Polyakov, and Sergey N. Mikhailov. "Strained Conformations of Nucleosides in Active Sites of Nucleoside Phosphorylases." Biomolecules 10, no. 4 (April 5, 2020): 552. http://dx.doi.org/10.3390/biom10040552.

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Nucleoside phosphorylases catalyze the reversible phosphorolysis of nucleosides to heterocyclic bases, giving α-d-ribose-1-phosphate or α-d-2-deoxyribose-1-phosphate. These enzymes are involved in salvage pathways of nucleoside biosynthesis. The level of these enzymes is often elevated in tumors, which can be used as a marker for cancer diagnosis. This review presents the analysis of conformations of nucleosides and their analogues in complexes with nucleoside phosphorylases of the first (NP-1) family, which includes hexameric and trimeric purine nucleoside phosphorylases (EC 2.4.2.1), hexameric and trimeric 5′-deoxy-5′-methylthioadenosine phosphorylases (EC 2.4.2.28), and uridine phosphorylases (EC 2.4.2.3). Nucleosides adopt similar conformations in complexes, with these conformations being significantly different from those of free nucleosides. In complexes, pentofuranose rings of all nucleosides are at the W region of the pseudorotation cycle that corresponds to the energy barrier to the N↔S interconversion. In most of the complexes, the orientation of the bases with respect to the ribose is in the high-syn region in the immediate vicinity of the barrier to syn ↔ anti transitions. Such conformations of nucleosides in complexes are unfavorable when compared to free nucleosides and they are stabilized by interactions with the enzyme. The sulfate (or phosphate) ion in the active site of the complexes influences the conformation of the furanose ring. The binding of nucleosides in strained conformations is a characteristic feature of the enzyme–substrate complex formation for this enzyme group.

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12

Franchetti, P., L. Messini, L. Cappellacci, M. Grifantini, G. Nocentini, P. Guarracino, M. E. Marongiu, and P. la Colla. "8-Aza Derivatives of 3-Deazapurine Nucleosides. Synthesis and in vitro Evaluation of Antiviral and Antitumor Activity." Antiviral Chemistry and Chemotherapy 4, no. 6 (December 1993): 341–52. http://dx.doi.org/10.1177/095632029300400606.

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The syntheses of 4-amino-1-(β-D-ribofuranosyl)-1 H-1,2,3-triazolo[4,5-c]pyridine (8-aza-3-deazaadenosine, 1), 4-amino-1-(2-deoxy-β-D- erythro-pentofuranosyl)-1 H-1,2,3-triazolo[4,5-c]pyridine (2′-deoxy-8-aza-3-deazaadenosine, 2), and their N8 and N7 glycosylated analogues (12,13, 21,22) and 4-amino-1-(2,3-dideoxy-β-D- erythro-pentof uranosyl)-1 H-1,2,3-triazolo [4,5-c]pyridine (2′,3′-dideoxy-8-aza-3-deazaadenosine, 3) were carried out by glycosylation of the 4-chloro-3 H-1,2,3-triazolo[4,5-c]pyridine anion. The anomeric configuration as well as the position of glycosylation were determined by 1H-, 13C-NMR, UV and N.O.E. difference spectroscopy. Nucleoside (2) and its parent compound 2′-deoxy-3-deazaadenosine were found active against ASFV and VSV. The 4-chloro-2-(β-D-ribofuranosyl)-2 H-1,2,3-triazolo[4,5-c] pyridine (9) was active against Coxsackie B1, whereas none of the 8-aza-3-deaza purine nucleosides, compound (3) included, was active against HIV-1. The 6-chloro derivatives of 8-aza-3-deazapurine ribo- and 2′-deoxyribonucleosides (11) and (20) showed some activity against LoVo human colon adenocarcinoma.

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13

Krečmerová, Marcela, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "Preparation of Purine 2'-Deoxy-5'-O-phosphonomethylnucleosides and 2'-Deoxy-3'-O-phosphonomethylnucleosides." Collection of Czechoslovak Chemical Communications 58, no. 2 (1993): 421–34. http://dx.doi.org/10.1135/cccc19930421.

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Sodium salt of 2'-deoxy-N6-dimethylaminomethylene-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (VIII) reacted with dibenzyl p-toluenesulfonyloxymethanephosphonate (Ia) to give dibenzyl ester of 2'-deoxy-N6-dimethylaminomethylene-5'-O-phosphonomethyl-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (XI) which after deprotection afforded the final 2'-deoxy-5'-O-phosphonomethyladenosine (XII). 2'-Deoxy-5'-O-hydroxymethanephosphonyladenosine (XIV) and 5'-O-benzyloxymethanephosphonyl-2'-deoxyadenosine (XIII) were isolated as a side product. The preparation of 2'-deoxy-5'-O-phosphonomethylguanosine (XVI) and protection of the starting nucleoside were analogous to those of compound XII. In the 2'-deoxy-3'-O-phosphonomethylnucleosides series, 2'-deoxy-3'-O-phosphonomethylcytidine (XXI) and 2'-deoxy-3'-O-phosphonomethyladenosine (XXVII) were prepared, using N4-benzoyl-5'-O-tert-butyldiphenylsilyl-2'-deoxycytidine (XVIII) and 5'-O-tert-butyldiphenylsilyl-2'-deoxy-N6-dimethylaminomethyleneadenosine (XXIV), respectively, as starting compounds.

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14

Votruba, Ivan, Antonín Holý, Hana Dvořáková, Jaroslav Günter, Dana Hocková, Hubert Hřebabecký, Tomas Cihlar, and Milena Masojídková. "Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells." Collection of Czechoslovak Chemical Communications 59, no. 10 (1994): 2303–30. http://dx.doi.org/10.1135/cccc19942303.

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Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of E. coli catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording N9-isomers in the purine and N1-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of N7-nitrogen atom. On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding N-dimethylaminomethylene derivative which is then ammonolyzed. The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-dideoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

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15

Stepchenko, Vladimir A., Anatoly I. Miroshnikov, Frank Seela, and Igor A. Mikhailopulo. "Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases." Beilstein Journal of Organic Chemistry 12 (December 1, 2016): 2588–601. http://dx.doi.org/10.3762/bjoc.12.254.

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The trans-2-deoxyribosylation of 4-thiouracil (4SUra) and 2-thiouracil (2SUra), as well as 6-azauracil, 6-azathymine and 6-aza-2-thiothymine was studied using dG and E. coli purine nucleoside phosphorylase (PNP) for the in situ generation of 2-deoxy-α-D-ribofuranose-1-phosphate (dRib-1P) followed by its coupling with the bases catalyzed by either E. coli thymidine (TP) or uridine (UP) phosphorylases. 4SUra revealed satisfactory substrate activity for UP and, unexpectedly, complete inertness for TP; no formation of 2’-deoxy-2-thiouridine (2SUd) was observed under analogous reaction conditions in the presence of UP and TP. On the contrary, 2SU, 2SUd, 4STd and 2STd are good substrates for both UP and TP; moreover, 2SU, 4STd and 2’-deoxy-5-azacytidine (Decitabine) are substrates for PNP and the phosphorolysis of the latter is reversible. Condensation of 2SUra and 5-azacytosine with dRib-1P (Ba salt) catalyzed by the accordant UP and PNP in Tris∙HCl buffer gave 2SUd and 2’-deoxy-5-azacytidine in 27% and 15% yields, respectively. 6-Azauracil and 6-azathymine showed good substrate properties for both TP and UP, whereas only TP recognizes 2-thio-6-azathymine as a substrate. 5-Phenyl and 5-tert-butyl derivatives of 6-azauracil and its 2-thioxo derivative were tested as substrates for UP and TP, and only 5-phenyl- and 5-tert-butyl-6-azauracils displayed very low substrate activity. The role of structural peculiarities and electronic properties in the substrate recognition by E. coli nucleoside phosphorylases is discussed.

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16

Yoshimura, Yuichi, Kenji Kitano, Kohei Yamada, Shinji Sakata, Shinji Miura, Noriyuki Ashida, and Haruhiko Machida. "Synthesis and biological activities of 2′-deoxy-2′-fluoro-4′-thioarabinofuranosylpyrimidine and -purine nucleosides." Bioorganic & Medicinal Chemistry 8, no. 7 (July 2000): 1545–58. http://dx.doi.org/10.1016/s0968-0896(00)00065-1.

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17

Kobayashi, Masayuki, Koichi Saito, Shigeru Tamogami, Junko Takashima, Kano Kasuga, and Ikuo Kojima. "Identification of a 2-cell stage specific inhibitor of the cleavage of preimplantation mouse embryos synthesized by rat hepatoma cells as 5′-deoxy-5′-methylthioadenosine." Zygote 19, no. 2 (June 23, 2010): 117–25. http://dx.doi.org/10.1017/s0967199410000158.

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SummaryRat hepatoma Reuber H-35 cells produce a unique compound designated as Fr.B-25, a 2-cell stage-specific inhibitor of the cleavage of preimplantation mouse embryos cultured in vitro. Here, we identified Fr.B-25 as a purine nucleoside, 5′-deoxy-5′-methylthioadenosine (MTA), by mass spectroscopic analysis. All of the biological activities examined of authentic MTA on the development of mouse zygotes were indistinguishable from those of Fr.B-25. The mechanism of MTA action in the development of preimplantation mouse embryos was probably different from those of hypoxanthine and adenosine, which are well-characterized purine nucleosides that act as inhibitors of the cleavage of mouse 2-cell embryos. From the shared molecular and biological properties of Fr.B-25 and MTA, we concluded that Fr.B-25 is MTA. To the best of our knowledge, this is the first delineation of the effect of MTA on the development of preimplantation mammalian embryos cultured in vitro.

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18

Koga, Masakazu, and Stewart W. Schneller. "The synthesis of two 2′-deoxy carbocyclic purine nucleosides lacking the 5′-methylene." Tetrahedron Letters 31, no. 41 (January 1990): 5861–64. http://dx.doi.org/10.1016/s0040-4039(00)97979-6.

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19

VAN DRAANEN, N. A., G. A. FREEMAN, S. A. SHORT, R. HARVEY, R. JANSEN, G. SZCZECH, and G. W. KOSZALKA. "ChemInform Abstract: Synthesis and Antiviral Activity of 2′-Deoxy-4′-thio Purine Nucleosides." ChemInform 27, no. 19 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199619253.

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20

Fraser, Allister, Patrick Wheeler, P. Dan Cook, and Yogesh S. Sanghvi. "Synthesis and conformational properties of 2′-deoxy-2′-methylthio-pyrimidine and -purine nucleosides: Potential antisense applications." Journal of Heterocyclic Chemistry 30, no. 5 (October 1993): 1277–87. http://dx.doi.org/10.1002/jhet.5570300518.

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21

Wirsching, Jörn, Jürgen Voss, Gunadi Adiwidjaja, Anja Giesler, and Jürgen Kopf. "Synthesis and Structural Elucidation of 2′-Deoxy-4′-thio-L-threo-pentofuranosylpyrimidine and -purine Nucleosides." European Journal of Organic Chemistry 2001, no. 6 (March 2001): 1077–87. http://dx.doi.org/10.1002/1099-0690(200103)2001:6<1077::aid-ejoc1077>3.0.co;2-0.

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22

KOGA, M., and S. W. SCHNELLER. "ChemInform Abstract: The Synthesis of Two 2′-Deoxy Carbocyclic Purine Nucleosides Lacking the 5′-Methylene." ChemInform 22, no. 39 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199139243.

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23

Yuejun Xiang, Lakshmi P. Kotra, Chung K. Chu, and Raymond F. Schinazi. "Synthesis and anti-HIV activities of 2′-deoxy-2′,2″-difluoro-β-L-ribofuranosyl-pyrimidine and -purine nucleosides." Bioorganic & Medicinal Chemistry Letters 5, no. 7 (April 1995): 743–48. http://dx.doi.org/10.1016/0960-894x(95)00107-5.

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24

FRASER, A., P. WHEELER, P. D. COOK, and Y. S. SANGHVI. "ChemInform Abstract: Synthesis and Conformational Properties of 2′-Deoxy-2′- methylthiopyrimidine and -purine Nucleosides: Potential Antisense Applications." ChemInform 25, no. 15 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199415266.

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25

Hossain, Nafizal, Berthold Wroblowski, Arthur Van Aerschot, Jef Rozenski, Andre De Bruyn, and Piet Herdewijn. "Oligonucleotides Composed of 2‘-Deoxy-1‘,5‘-anhydro-d-mannitol Nucleosides with a Purine Base Moiety." Journal of Organic Chemistry 63, no. 5 (March 1998): 1574–82. http://dx.doi.org/10.1021/jo9718511.

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26

Ma, Tianwei, Ju-Sheng Lin, M. Gary Newton, Yung-Chi Cheng, and Chung K. Chu. "Synthesis and Anti-Hepatitis B Virus Activity of 9-(2-Deoxy-2-fluoro-β-l-arabinofuranosyl)purine Nucleosides." Journal of Medicinal Chemistry 40, no. 17 (August 1997): 2750–54. http://dx.doi.org/10.1021/jm970233+.

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27

Sivets, Grigorii G. "Syntheses of 2′-deoxy-2′-fluoro-β-d-arabinofuranosyl purine nucleosides via selective glycosylation reactions of potassium salts of purine derivatives with the glycosyl bromide." Tetrahedron Letters 57, no. 3 (January 2016): 268–71. http://dx.doi.org/10.1016/j.tetlet.2015.11.091.

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28

Yamada, Kohei, Noritake Matsumoto, and Hiroyuki Hayakawa. "Stereoselective Synthesis of 2-Deoxy-2-Fluoroarabinofuranosyl-α-1-Phosphate and Its Application to the Synthesis of 2′-Deoxy-2′-Fluoroarabinofuranosyl Purine Nucleosides by a Chemo-Enzymatic Method." Nucleosides, Nucleotides and Nucleic Acids 28, no. 11-12 (December 7, 2009): 1117–30. http://dx.doi.org/10.1080/15257770903396741.

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29

MA, T., J. S. LIN, M. G. NEWTON, Y. C. CHENG, and C. K. CHU. "ChemInform Abstract: Synthesis and Anti-Hepatitis B Virus Activity of 9-(2-Deoxy-2-fluoro-. beta.-L-arabinofuranosyl)purine Nucleosides." ChemInform 28, no. 49 (August 2, 2010): no. http://dx.doi.org/10.1002/chin.199749245.

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30

Kim, Hea Ok, Lak Shin Jeong, Sun Nan Lee, Soo Jeong Yoo, Hyung Ryong Moon, Kil Soo Kim, and Moon Woo Chun. "A highly efficient synthesis of L-β-2′-deoxy-4′-thio-1′-purine nucleosides as potential antiviral agents." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (2000): 1327–29. http://dx.doi.org/10.1039/b001240h.

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31

GUEDJ, R., E. E. E. SUHAS, P. R. T. FROGIER, R. CONDOM, S. R. CHALLAND, A. KIRN, and A. M. AUBERTIN. "SYNTHESIS AND BIOLOGICAL EVALUATION OF NEW CARBOCYCLIC 2??,3??-DIDEHYDRO-2??,3??-DIDEOXY AND 3??-DEOXY-2??-FLUORO PYRIMIDINE AND PURINE NUCLEOSIDES." AIDS 8, Supplement 4 (November 1994): S33. http://dx.doi.org/10.1097/00002030-199411004-00127.

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32

Clark, Jeremy L., J. Christian Mason, Laurent Hollecker, Lieven J. Stuyver, Phillip M. Tharnish, Tamara R. McBrayer, Michael J. Otto, Phillip A. Furman, Raymond F. Schinazi, and Kyoichi A. Watanabe. "Synthesis and antiviral activity of 2′-deoxy-2′-fluoro-2′-C-methyl purine nucleosides as inhibitors of hepatitis C virus RNA replication." Bioorganic & Medicinal Chemistry Letters 16, no. 6 (March 2006): 1712–15. http://dx.doi.org/10.1016/j.bmcl.2005.12.002.

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33

Kohgo, Satoru, Kohei Yamada, Kenji Kitano, Yuko Iwai, Shinji Sakata, Noriyuki Ashida, Hiroyuki Hayakawa, et al. "Design, Efficient Synthesis, and Anti‐HIV Activity of 4′‐C‐Cyano‐ and 4′‐C‐Ethynyl‐2′‐deoxy Purine Nucleosides." Nucleosides, Nucleotides and Nucleic Acids 23, no. 4 (December 31, 2004): 671–90. http://dx.doi.org/10.1081/ncn-120037508.

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34

SAMANO, V., and M. J. ROBINS. "ChemInform Abstract: Nucleic Acid Related Compounds. Part 60. Mild Periodinane Oxidation of Protected Nucleosides to give 2′- and 3′-Keto Nucleosides. The First Isolation of a Purine 2′-Deoxy 3′-Keto Nucleoside Derivative." ChemInform 22, no. 6 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199106286.

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35

Hocek, Michal, Antonín Holý, Ivan Votruba, and Hana Dvořáková. "Cytostatic 6-Arylpurine Nucleosides II. Synthesis of Sugar-Modified Derivatives: 9-(2-Deoxy-β-D-erythro-pentofuranosyl)-, 9-(5-Deoxy-β-D-ribofuranosyl)- and 9-(2,3-Dihydroxypropyl)-6-phenylpurines." Collection of Czechoslovak Chemical Communications 65, no. 11 (2000): 1683–97. http://dx.doi.org/10.1135/cccc20001683.

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9-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-(4-substituted phenyl)purines, 9-(5-deoxy-β-D-ribofuranosyl)-6-(4-substituted phenyl)purines and 9-(2,3-dihydroxypropyl)-6-(4-substituted phenyl)purines were prepared by the Suzuki-Miyaura cross-coupling reactions of the corresponding protected 9-substituted 6-chloropurines with substituted phenylboronic acids followed by MeONa mediated deprotection. In contrast to the highly active 6-phenylpurine ribonucleosides, the title compounds did not show any considerable cytostatic activity.

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36

Kim, Hea Ok, Lak Shin Jeong, Sun Nan Lee, Soo Jeong Yoo, Hyung Ryong Moon, Kil Soo Kim, and Moon Woo Chun. "ChemInform Abstract: A Highly Efficient Synthesis of L-β-2′-Deoxy-4′-thio-1′-purine Nucleosides as Potential Antiviral Agents." ChemInform 31, no. 32 (June 3, 2010): no. http://dx.doi.org/10.1002/chin.200032181.

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37

Wirsching, Joern, Juergen Voss, Gunadi Adiwidjaja, Anja Giesler, and Juergen Kopf. "ChemInform Abstract: Thiosugars. Part 7. Synthesis and Structural Elucidation of 2′-Deoxy-4′-thio-L-threo-pentofuranosylpyrimidine and -purine Nucleosides." ChemInform 33, no. 9 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200209229.

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38

Rabuffetti, Marco, Teodora Bavaro, Riccardo Semproli, Giulia Cattaneo, Michela Massone, Carlo F. Morelli, Giovanna Speranza, and Daniela Ubiali. "Synthesis of Ribavirin, Tecadenoson, and Cladribine by Enzymatic Transglycosylation." Catalysts 9, no. 4 (April 12, 2019): 355. http://dx.doi.org/10.3390/catal9040355.

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Despite the impressive progress in nucleoside chemistry to date, the synthesis of nucleoside analogues is still a challenge. Chemoenzymatic synthesis has been proven to overcome most of the constraints of conventional nucleoside chemistry. A purine nucleoside phosphorylase from Aeromonas hydrophila (AhPNP) has been used herein to catalyze the synthesis of Ribavirin, Tecadenoson, and Cladribine, by a “one-pot, one-enzyme” transglycosylation, which is the transfer of the carbohydrate moiety from a nucleoside donor to a heterocyclic base. As the sugar donor, 7-methylguanosine iodide and its 2′-deoxy counterpart were synthesized and incubated either with the “purine-like” base or the modified purine of the three selected APIs. Good conversions (49–67%) were achieved in all cases under screening conditions. Following this synthetic scheme, 7-methylguanine arabinoside iodide was also prepared with the purpose to synthesize the antiviral Vidarabine by a novel approach. However, in this case, neither the phosphorolysis of the sugar donor, nor the transglycosylation reaction were observed. This study was enlarged to two other ribonucleosides structurally related to Ribavirin and Tecadenoson, namely, Acadesine, or AICAR, and 2-chloro-N6-cyclopentyladenosine, or CCPA. Only the formation of CCPA was observed (52%). This study paves the way for the development of a new synthesis of the target APIs at a preparative scale. Furthermore, the screening herein reported contributes to the collection of new data about the specific substrate requirements of AhPNP.

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39

López-Zavala, Alonso A., Idania E. Quintero-Reyes, Jesús S. Carrasco-Miranda, Vivian Stojanoff, Andrzej Weichsel, Enrique Rudiño-Piñera, and Rogerio R. Sotelo-Mundo. "Structure of nucleoside diphosphate kinase from pacific shrimp (Litopenaeus vannamei) in binary complexes with purine and pyrimidine nucleoside diphosphates." Acta Crystallographica Section F Structural Biology Communications 70, no. 9 (August 29, 2014): 1150–54. http://dx.doi.org/10.1107/s2053230x1401557x.

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Nucleoside diphosphate kinase (NDK; EC 2.7.4.6) is an enzyme that catalyzes the third phosphorylation of nucleoside diphosphates, leading to nucleoside triphosphates for DNA replication. Expression of the NDK fromLitopenaeus vannamei(LvNDK) is known to be regulated under viral infection. Also, as determined by isothermal titration calorimetry,LvNDK binds both purine and pyrimidine deoxynucleoside diphosphates with high binding affinity for dGDP and dADP and with no heat of binding interaction for dCDP [Quintero-Reyeset al.(2012),J. Bioenerg. Biomembr.44, 325–331]. In order to investigate the differences in selectivity,LvNDK was crystallized as binary complexes with both acceptor (dADP and dCDP) and donor (ADP) phosphate-group nucleoside diphosphate substrates and their structures were determined. The three structures with purine or pyrimidine nucleotide ligands are all hexameric. Also, the binding of deoxy or ribonucleotides is similar, as in the former a water molecule replaces the hydrogen bond made by Lys11 to the 2′-hydroxyl group of the ribose moiety. This allows Lys11 to maintain a catalytically favourable conformation independently of the kind of sugar found in the nucleotide. Because of this, shrimp NDK may phosphorylate nucleotide analogues to inhibit the viral infections that attack this organism.

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40

Krzeminski, Jacek, Barbara Nawrot, Krzysztof W. Pankiewicz, and Kyoichi A. Watanabe. "Synthesis of 9-(2-Deoxy-2-Fukuoro-β-D- Abinoruranosyl)Hypoxhine. The First Direct Introduction of A 2′-β-Fldoro Substituent in Ppepormed Purine Nucleosides. Studies Directed Toward the Synthesis of 2′-DEOXY-2′-Substituted Arabppmocebosides. 8.1." Nucleosides and Nucleotides 10, no. 4 (June 1991): 781–98. http://dx.doi.org/10.1080/07328319108046662.

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41

Wauchope, Orrette R., Cameron Johnson, Pasupathy Krishnamoorthy, Graciela Andrei, Robert Snoeck, Jan Balzarini, and Katherine L. Seley-Radtke. "Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2′-deoxy nucleoside analogues." Bioorganic & Medicinal Chemistry 20, no. 9 (May 2012): 3009–15. http://dx.doi.org/10.1016/j.bmc.2012.03.004.

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42

Wnuk, Stanislaw F., Elzbieta Lewandowska, Dania R. Companioni, Pedro I. Garcia Jr, and John A. Secrist III. "Synthesis and cytotoxicity of 9-(2-deoxy-2-alkyldithio-β-D-arabinofuranosyl)purine nucleosides which are stable precursors to potential mechanistic probes of ribonucleotide reductases." Org. Biomol. Chem. 2, no. 1 (2004): 120–26. http://dx.doi.org/10.1039/b311504f.

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43

Franchetti, Palmarisa, Loredana Cappellacci, Mario Grifantini, Giulio Lupidi, Giuseppe Nocentini, and Anna Barzi. "8-Aza Analogues of Deaza Purine Nucleosides. Synthesis and Biological Evaluation of 8-Aza-1-deazaadenosine and 2′-Deoxy-8-aza-1-deazaadenosine." Nucleosides and Nucleotides 11, no. 5 (June 1992): 1059–76. http://dx.doi.org/10.1080/07328319208021168.

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44

Jiricny, Josef. "N6-Methoxyadenine-Pyrimidine Base Pairs as Substrates for the Mismatch Repair System of Escherichia coli." Collection of Czechoslovak Chemical Communications 66, no. 7 (2001): 1107–24. http://dx.doi.org/10.1135/cccc20011107.

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The availability of nucleoside analogues with ambiguous base-pairing properties would be of considerable value in molecular biology. We have incorporated deoxynebularine [9-(2-deoxy-β-D-ribofuranosyl)purine, P], deoxyinosine [9-(2-deoxy-β-D-ribofuranosyl)-6-hydroxypurine, I) and [9-(2-deoxy-β-D-ribofuranosyl)-6-methoxyaminopurine, MeOA] into hexadecamer oligodeoxyribonucleotides and tested their behaviour in DNA•DNA hybridisations in vitro, as well as in oligonucleotide-directed mutagenesis experiments in vivo. The results showed that P behaved as an adenine analogue in all assays. Oligonucleotide duplexes containing I/C or I/T base pairs displayed similar thermal stabilities in DNA•DNA hybridisation experiments, however, during DNA synthesis in vitro and in vivo, hypoxanthine behaved strictly as a guanine analogue. Only MeOA was truly ambiguous in all assays. The 1H NMR spectrum of the nucleoside demonstrated the existence of two distinct tautomeric forms in a ratio of ca 8 : 2, implying that the base might pair with both C and T. Indeed, within the context of synthetic hexadecamer duplexes, MeOA/C and MeOA/T pairs brought about a similar thermal destabilisation, with the former base pair being only marginally less favoured. When used as hybridisation probes on single-stranded M13 DNA, the MeOA-containing hexadecamer oligonucleotides were shown to bind with similar efficiencies to target sequences containing either C or T opposite the analogue. Interestingly, when MeOA is in the template strand during DNA replication, the polymerase III holoenzyme of E. coli reads it predominantly as a G, which indicates that MeOA exists in B-DNA mostly as the anti-imino tautomer.

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45

Kakefuda, Akio, Satoshi Shuto, Takemitsu Nagahata, Jun-ichi Seki, Takuma Sasaki, and Akira Matsuda. "Nucleosides and nucleotides. 132. Synthesis and biological evaluations of ring-expanded oxetanocin analogues: Purine and pyrimidine analogues of 1,4-anhydro-2-deoxy-d-arabitol and 1,4-anhydro-2-deoxy-3-hydroxymethyl-d-arabitol." Tetrahedron 50, no. 34 (August 1994): 10167–82. http://dx.doi.org/10.1016/s0040-4020(01)81749-x.

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46

Elwi, Adam N., Vijaya L. Damaraju, Michelle L. Kuzma, Delores A. Mowles, Stephen A. Baldwin, James D. Young, Michael B. Sawyer, and Carol E. Cass. "Transepithelial fluxes of adenosine and 2′-deoxyadenosine across human renal proximal tubule cells: roles of nucleoside transporters hENT1, hENT2, and hCNT3." American Journal of Physiology-Renal Physiology 296, no. 6 (June 2009): F1439—F1451. http://dx.doi.org/10.1152/ajprenal.90411.2008.

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This study examined the roles of human nucleoside transporters (hNTs) in mediating transepithelial fluxes of adenosine, 2′-deoxyadenosine, and three purine nucleoside anti-cancer drugs across polarized monolayers of human renal proximal tubule cells (hRPTCs), which were shown in previous studies to have human equilibrative NT 1 (hENT1) and 2 (hENT2) and human concentrative NT 3 (hCNT3) activities ( 11 ). Early passage hRPTCs were cultured on transwell inserts under conditions that induced formation of polarized monolayers with experimentally accessible apical and basolateral domains. Polarized hRPTC cultures were monitored for inhibitor sensitivities and sodium-dependence of the following: 1) transepithelial fluxes of radiolabeled adenosine, 2′-deoxyadenosine, fludarabine (9-β-d-arabinosyl-2-fluoroadenine), cladribine (2-chloro-2′-deoxyadenosine), and clofarabine (2-chloro-2′-fluoro-deoxy-9-β-d-arabinofuranosyladenine); 2) mediated uptake of radiolabeled adenosine, 2′-deoxyadenosine, fludarabine, cladribine, and clofarabine from either apical or basolateral surfaces; and 3) relative apical cell surface hCNT3 protein levels. Transepithelial fluxes of adenosine were mediated from apical-to-basolateral sides by apical hCNT3 and basolateral hENT2, whereas transepithelial fluxes of 2′-deoxyadenosine were mediated from basolateral-to-apical sides by apical hENT1 and basolateral human organic anion transporters (hOATs). The transepithelial fluxes of adenosine, hCNT3-mediated cellular uptake of adenosine, and relative apical cell surface hCNT3 protein levels correlated positively in polarized hRPTCs. The purine nucleoside anti-cancer drugs fludarabine, cladribine, and clofarabine, like adenosine exhibited apical-to-basolateral fluxes. Collectively, this evidence suggested that apical hCNT3 and basolateral hENT2 are involved in proximal tubular reabsorption of adenosine and some nucleoside drugs and that apical hENT1 and basolateral hOATs are involved in proximal tubular secretion of 2′-deoxyadenosine.

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CHU, Chung K., Jasenka MATULIC-ADAMIC, Jai-Tung HUANG, Ting-Chao CHOU, Joseph H. BURCHENAL, Jack J. FOX, and Kyoichi A. WATANABE. "Nucleosides. CXXXV. Synthesis of some 9-(2-deoxy-2-fluoro-.BETA.-D-arabinofuranosyl)-9H-purines and their biological activities." CHEMICAL & PHARMACEUTICAL BULLETIN 37, no. 2 (1989): 336–39. http://dx.doi.org/10.1248/cpb.37.336.

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48

Chang, Junbiao, Baojuan Zhao, Qiang Wang, Yunfei Du, and Kang Zhao. "Design and Synthesis of 3′-Deoxy-3′-Fluoro-2′-O,3′-C-Vinylene-Linked Bicyclic Purine Nucleoside." Synlett 2008, no. 19 (November 12, 2008): 2993–96. http://dx.doi.org/10.1055/s-0028-1087227.

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49

Samano, Vicente, and Morris J. Robins. "Nucleic acid related compounds. 60. Mild periodinane oxidation of protected nucleosides to give 2'- and 3'-ketonucleosides. The first isolation of a purine 2'-deoxy-3'-ketonucleoside derivative." Journal of Organic Chemistry 55, no. 18 (August 1990): 5186–88. http://dx.doi.org/10.1021/jo00305a003.

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50

Hanna, Naeem B., Kandasamy Ramasamy, Roland K. Robins, and Ganapathi R. Revankar. "A convenient synthesis of 2′-deoxy-6-thioguanosine,ara-guanine,ara-6-thioguanine and certain related purine nucleosides by the stereospecific sodium salt glycosylation procedure." Journal of Heterocyclic Chemistry 25, no. 6 (November 1988): 1899–903. http://dx.doi.org/10.1002/jhet.5570250653.

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