• Journal of Life Science
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• v.9 no.1
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• pp.58-62
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• 1999

Several nucleoside 5'-monophosphate analogues and lipophilic nucleoside 5'-(3-pyridinylcarbonyl)monophosphate analogues were synthesized. Antitumor activities of the synthesized nucleoside malogues against P338 mouse leukemia, FM3A murine mammary carcinoma, and U937 human histiocytic lymphoma cells were determined by MTT assay. Antitumor activities of the lipophilic uridine 5'-(3-pyridinylcarbonyl) monophosphate(7) and 2',3'-didehydro-3'-deoxy-thymidine-5'-(3-pyridinylcarbonyl) monophosphate(8) were stronger than those of uridine 5'-monophosphate(1) and 2',3'-didehydro-3'-deoxythymidine-5'-monophosphate(4). This preliminary experimental result suggests that nucleoside 5'-(3-pyridinylcar-bonyl)monophosphate analogues may be new prodrugs to overcome the clinical limit.

• Microbiology and Biotechnology Letters
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• v.21 no.1
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• pp.23-29
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• 1993

A bacterial strain. producing a nucleoside oxidase was isolated from soil and identified as Flavobacterium meningosepticum by its taxonomical characteristics. The enzyme has been purified ISO-fold to electrophoretic homogeniety in an overall yield of 18% from the cell free extract of the producer. The enzyme catalyzed oxidation of only nucleosides related to both purine and pyrimidine with very high substrate specificity. The nucleoside oxidase was proved to be a noble enzyme by stoichiometry that 1 mol adenosine as a substrate was especially oxidized via adenosine 5' -aldehyde to 1 mol adenosine 5' -carboxylic acid with the formation of 2 mol $H_20_2$

• Bulletin of the Korean Chemical Society
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• v.25 no.5
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• pp.668-672
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• 2004

This paper reports the stereoselective synthesis of a novel nucleoside, 4'-methyl branched and bicyclo [3.1.0] hexane locked-nucleoside 12, using a sequential [3,3]-sigmatropic rearrangement/carbene cycloaddition reaction/Curtius reaction strategy with a high stereoselectivity.

• Microbiology and Biotechnology Letters
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• v.24 no.6
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• pp.693-698
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• 1996

Optimal cultural conditions were investigated for the maximal productivity of nucleoside oxidase and peroxidase from Flavobacterium meningosepticum. Sucrose and Polypepton were the best as a carbon source and a nitrogen source. Fe$^{2+}$, Fe$^{3+}$ and Cu$^{2+}$ increased the activities of the two enzymes and were essential in medium containing peptone as a nitrogen source. Nucleoside derivatives such as 2'-deoxyguanosine, 2'-deoxyadenosine, N$^{6}$ -methyladenosine and 1-methyladenosine were effective for the production of the two enzymes. Especially, the addition of N$^{6}$ -methyladenosine and 1-methyladenosine decreased cell growth, but increased the two enzyme activities. High level of oxygen also was an essential factor for formation and/or induction of these enzymes. From the summary of this study about optimal medium and environmental conditions, nucleoside oxidase was biosynthesized in proportion to peroxidase. These results suggested that the role of peroxidase should be degradation of H$_{2}$O$_{2}$ generated by nucleoside oxidase in the cell of Flavobacterium meningosepticum.

• Bulletin of the Korean Chemical Society
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• v.34 no.3
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• pp.868-874
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• 2013

Efficient synthetic route to novel 2'-spirocyclopropanoid 4'-deoxythreosyl phosphonic acid nucleosides was described from 1,4-dihydroxy-2-butene. Cyclopropane moiety was prepared via ester enolate alkylation using (2-chloroethyl)dimethylsulfonium iodide. Synthesized nucleoside analogues 16, 19, 23 and 26 were tested for anti-HIV activity as well as cytotoxicity. However, none of them showed any anti-HIV activity or cytotoxicity up to 100 ${\mu}M$.

• Bulletin of the Korean Chemical Society
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• v.24 no.9
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• pp.1289-1292
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• 2003

An efficient synthetic route for preparing novel $4'{\alpha}$-C phenyl branched carbocyclic nucleoside is described. The installation of phenyl group at the $4'$-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) beginning from simple ketone such as 2-hydroxy acetophenone.

• Bulletin of the Korean Chemical Society
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• v.26 no.9
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• pp.1366-1368
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• 2005

The first synthesis of a 4'-branched carbocyclic C-nucleoside 11 was achieved via the key intermediate 6, which was prepared using Knovenagel type condensation from ketone derivative 4.

• Journal of Integrative Natural Science
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• v.8 no.3
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• pp.153-163
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• 2015

Racemic synthesis of novel 5',5'-difluoro-2'-methyl-apiose nucleoside phosphonic acid analogs was achieved as potent antiviral agents. Phosphonation was performed by direct displacement of triflate intermediate with diethyl (lithiodifluoromethyl) phosphonate to give the corresponding (${\alpha},{\alpha}$-difluoroalkyl) phosphonate. Condensation successfully proceeded from a glycosyl donor with persilylated bases to yield the nucleoside phosphonate analogs. Deprotection of diethyl phosphonates provided the target nucleoside analogs. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the pyrimidine analogs (cytosine, uracil, and thymine) have weak anti-HIV or HCMV activity.

• Microbiology and Biotechnology Letters
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• v.24 no.5
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• pp.579-584
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• 1996

The molecular weight of the purified nucleoside oxidase estimated by gel filtration column chromatography was 480,000 and the enzyme protein was composed of four nonidentical subunits (81,000, 69,000, 32,000 and 16,000). On the basis of the visible absorption spectra and the enzymatic determination of the purified enzyme, the enzyme was supposed as a hemoprotein and also a flavoprotein containing 3 moles of FAD per I mole of enzyme. The isoelectric point of the enzyme was pH 5.1. Addition of metal salts such as 1 mM SnCl$_{2}$ and PbCl$_{2}$ into an enzyme reaction solution inhibited the enzyme activity by 94 and 90%, respectively. The enzyme activity was also lost significantly by hemoenzyme inhibitors such as NaCN and NaN$_{3}$ and flavoenzyme inhibitor, acriflavine and quinacrine. The maximal nucleoside oxidase activity was observed at pH 7.0 and 55$\circ$C. The nucleoside oxidase was relatively stable in the range of pH 5.5-9.0 and below 55$\circ$C.

• Bulletin of the Korean Chemical Society
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• v.33 no.12
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• pp.4007-4014
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• 2012

Efficient synthetic route to novel 4'-fluorinated 5'-deoxythreosyl phosphonic acid nucleosides was described from glyceraldehyde using Horner-Emmons reaction in the presence of triethyl ${\alpha}$-fluorophosphonoacetate. Glycosylation reaction of nucleosidic bases with glycosly donor 14 gave the nucleosides which were further phosphonated and hydrolyzed to reach desired nucleoside analogues. Synthesized nucleoside analogues 18, 21, 25 and 28 were tested for anti-HIV activity as well as cytotoxicity. Adenine derivatives 18 and 21 showed significant anti-HIV activity up to $100{\mu}M$.