ChemInform Abstract: Synthesis and Antiviral Activity of 1‐(β‐D‐Arabinofuranosyl)thymine.

Kvasyuk, Е. I.; Кулак, Т. И.; Ткаченко, О. А.; Mikhailopulo, Igor A.; Zinchenko, A. I.; Barai, V. N.; Bokut, S. B.; Маренникова, С. С.; Chekunova, E. V.

doi:10.1002/chin.199005294

Cited by 3 publications

(11 citation statements)

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“…U, C-5, Th-5 ( fig. 1), and nucleosides dThd, Urd, five mixtures were prepared, with components according to previous recommendations 15: acyclonucleoside or nucleoside, 3.8 gmol; NPP, 46 gmol; biomass (dry weight) 10mg; ZnSO~, 10 gmol, and 0.2 M acetate buffer (pH 4.5) to 1 ml. Mixtures were incubated at 37 ~ and the progress of the reaction was monitored hourly using alkaline method chromatography on silica gel plates in conjunction with UV spectrophotometry.…”

Section: Resultsmentioning

confidence: 99%

“…Bacillus subtilis and Brevibacterium ammoniagenes, are already employed in biotechnological processes 12. The bacterium that has been chosen for the procedures described here -Enterobacter agglomerans (formerly Erwinia herbicola) -has not previously been used in biotechnology; it is readily available, easy to culture and provides a rapid and efficient supply of nucleotides [13][14][15]. No selection of the most active strains has been attempted because the main purpose of the investigation was to determine the effectiveness of the species as a whole, as a source of acyclonucleotides.…”

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confidence: 99%

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Biotransformation, byEnterobacter agglomerans, of pyrimidine acyclonucleosides to acyclonucleotides

Rutkowski¹,

Korczak²

1992

Experientia

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The ability of Enterobacter agglomerans to transform naturally occurring nucleosides into nucleotides has been utilized to transform newly synthesized pyrimidine acyclonucleosides into the corresponding acyclonucleotides. Unselected bacteria were used as the source of nucleoside phosphotransferase, the phosphate group donor being 4-nitrophenyl phosphate in the presence of Zn2+ ions. Optimal reaction conditions are outlined.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Biotransformation, byEnterobacter agglomerans, of pyrimidine acyclonucleosides to acyclonucleotides

Rutkowski¹,

Korczak²

1992

Experientia

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“…The principal types of biological activity are typical of compounds containing an oligonucleotide chain of at least three nucleoside units. Dephosphorylated oligomers 2 and their synthetic analogs, in particular, those containing 6-N-benzyladenosine (3) in various positions of the oligonucleotide chain exhibit interesting biological properties [6,9]. This nucleoside is a riboside of the natural phytohormone 6-N-benzylaminopurine (BAP) and possesses cytokine activity [10].…”

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“…(2′-5′)-Oligoadenylates are active toward animal and plant viruses [5,6] and affect on cell growth and development [7,8]. The principal types of biological activity are typical of compounds containing an oligonucleotide chain of at least three nucleoside units.…”

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confidence: 99%

Preparation of (2′-5′)-oligonucleotides based on 6-N-benzylaminopurineriboside using the Spicaria violacea fungal enzyme complex

Кулак¹,

Ткаченко²,

Grishan³

et al. 2009

Chem Nat Compd

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“…They are activators of latent endonuclease L, which hydrolyzes mRNA of viruses and is in several instances responsible for the antiviral effect of interferon [1][2][3]. Furthermore, (2′-5′)-oligoadenylates affect cell growth, differentiation, and proliferation and apoptosis [4,5], are active toward plant viruses [6,7], and induce cytokinic activity in plant tissues [8]. Various types of biological activity can appear not only for 1 but also for dephosphorylated derivatives [A(2′p5′A) n , 2] [9,10].…”

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Chemical enzymatic synthesis of (2′-5′)-oligoadenylates using nuclease from Spicaria violacea mycelial fungus

et al. 2007

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2′-5′)-Oligoadenylates [ppp5′A(2′p5′A) n , 1] are oligomers of adenylic acid with (2′-5′)-phosphodiester bonds that are synthesized in cells of mammals from 5′-ATP in the presence of interferon and/or double-helix RNA. They are activators of latent endonuclease L, which hydrolyzes mRNA of viruses and is in several instances responsible for the antiviral effect of interferon [1][2][3]. Furthermore, (2′-5′)-oligoadenylates affect cell growth, differentiation, and proliferation and apoptosis [4,5], are active toward plant viruses [6,7], and induce cytokinic activity in plant tissues [8]. Various types of biological activity can appear not only for 1 but also for dephosphorylated derivatives [A(2′p5′A) n , 2] [9, 10].Existing chemical methods for synthesizing these compounds are complicated and multi-step. Methods for preparing (2′-5′)-oligoadenylates that include polymerization of AMP derivatives to form both (2′-5′)-and (3′-5′)-internucleotide bonds and subsequent treatment of the resulting oligomers with several highly purified enzymes that selectively hydrolyze (3′-5′)-internucleotide bonds and terminal phosphates have been described [11][12][13]. The drawbacks of these methods are that they are labor-intensive due to the need to separate and purify several individual enzymes and the duration of the enzymatic steps.Herein we report the ability to use the filtrate of culture liquid (CL) of the mycelial fungus Spicaria violacea to produce (2′-5′)-oligoadenylates. It contains phosphatase and nuclease, which can hydrolyze (3′-5′)-but not (2′-5′)-internucleotide phosphodiester bonds in the chemically synthesized polynucleotides with mixed (2′-5′)-(3′-5′)-internucleotide bonds.We used S. violacea BIM F-329 strain from the Belorussian collection of nonpathogenic microorganisms of the Institute of Microbiology of the National Academy of Sciences of Belarus. The conditions for cultivating the fungus and the preparation of the CL filtrate containing phosphatase and nuclease have been described by us [14].Mixed (2′-5′)-(3′-5′)-polyadenylates were synthesized by polymerization of 2′(3′)-AMP in dioxane using diphenylchlorophosphate and tributylamine [11,12].Enzymatic hydrolysis of oligo-and polynucleotides by the enzyme complex in CL filtrate from S. violacea was carried out in Tris-HCl buffer (50 mM, pH 6.0) containing MgCl 2 (10 mM) at 60°C.The compositions of mixtures produced by enzymatic hydrolysis of polyadenylates were analyzed by HPLC on a Waters chromatograph using a Nova-Pak C18 column (30 × 3.9 mm) with elution by CH 3 CN (7%) in aqueous KH 2 PO 4 (0.1 M, pH 4.38) for 30 min. The chromatographic mobility of individual compounds in the mixture was compared with those of oligoadenylates of known phosphodiester bonding and chain length that were prepared by the triester synthesis method [15].The presence in S. violacea CL of phosphatase and specific nuclease that can hydrolyze only natural (3′-5′)-phosphodiester bonds was proved by experiments on the action of CL filtrate on polyadenylic acid that contained only (3′-5...

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ChemInform Abstract: Synthesis and Antiviral Activity of 1‐(β‐D‐Arabinofuranosyl)thymine.

Abstract: 1‐(β‐D‐Ribofuranosyl)thymine (V), prepared from thymine (I) via the protected riboside (IV) or by microbiological transglycosylation of inosine (VI), is converted into 1‐(β‐D‐arabinofuranosyl)thymine (VII) upon treatment with acetylsalicylic chloride.

Cited by 3 publications

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Biotransformation, byEnterobacter agglomerans, of pyrimidine acyclonucleosides to acyclonucleotides

Biotransformation, byEnterobacter agglomerans, of pyrimidine acyclonucleosides to acyclonucleotides

Preparation of (2′-5′)-oligonucleotides based on 6-N-benzylaminopurineriboside using the Spicaria violacea fungal enzyme complex

Chemical enzymatic synthesis of (2′-5′)-oligoadenylates using nuclease from Spicaria violacea mycelial fungus

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