- Ribose-modified adenosine analogues as potential partial agonists for the adenosine receptor
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We have adopted a practical three-step route for the synthesis of 2'- and 3'-deoxy analogues of N6-substituted adenosines: protection of the hydroxyl groups, replacement of the N6-amino by a better leaving group, and combined deprote
- Van der Wenden,Von Frijtag Drabbe Kunzel,Mathot,Danhof,Ijzerman,Soudijn
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- SELECTIVE N-DEACYLATION OF N,O-PROTECTED NUCLEOSIDES BY ZINC BROMIDE
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N-Acyl protecting group in nucleoside derivatives can be selectively removed by treatment with zinc bromide in the presence of alcohols to give O-protected nucleosides.
- Kierzek, R.,Ito, H.,Bhatt, R.,Itakura, K.
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- Spectral assignments and reference data complete1H and 13C NMR spectral assignment of α- And β-adenosine, 2′-deoxyadenosine and their acetate derivatives
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1H and 13C NMR chemical shifts of α- and β-anomers of adenosine, 2′-deoxyadenosine and their acetate derivatives were completely and definitely assigned using the concerted application of one- and two-dimensional experiments (gCOSY, gNOESY, gHSQC and gHMBC). The influence of the stereochemistry of the purine base on the NMR data of the hydrogen and carbon atoms of the furanose moiety was estimated. Copyright
- Ciuffreda,Casati,Manzocohi
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- Synthesis of fluorescent adenosine analogues
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In the synthesis of a transition state inhibitor of the enzyme adenylosuccinate lyase two different [2,1-i]-pyrimido-purine derivatives are formed, of which one might be very interesting for cell biological research, due to its strong fluorescent properties.
- De Boer,Petra,Wanner,Boesaart,Koomen
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- Amino Acid Modified RNA Bases as Building Blocks of an Early Earth RNA-Peptide World
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Fossils of extinct species allow us to reconstruct the process of Darwinian evolution that led to the species diversity we see on Earth today. The origin of the first functional molecules able to undergo molecular evolution and thus eventually able to create life, are largely unknown. The most prominent idea in the field posits that biology was preceded by an era of molecular evolution, in which RNA molecules encoded information and catalysed their own replication. This RNA world concept stands against other hypotheses, that argue for example that life may have begun with catalytic peptides and primitive metabolic cycles. The question whether RNA or peptides were first is addressed by the RNA-peptide world concept, which postulates a parallel existence of both molecular species. A plausible experimental model of how such an RNA-peptide world may have looked like, however, is absent. Here we report the synthesis and physicochemical evaluation of amino acid containing adenosine bases, which are closely related to molecules that are found today in the anticodon stem-loop of tRNAs from all three kingdoms of life. We show that these adenosines lose their base pairing properties, which allow them to equip RNA with amino acids independent of the sequence context. As such we may consider them to be living molecular fossils of an extinct molecular RNA-peptide world.
- Nainyt?, Milda,Müller, Felix,Ganazzoli, Giacomo,Chan, Chun-Yin,Crisp, Antony,Globisch, Daniel,Carell, Thomas
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supporting information
p. 14856 - 14860
(2020/10/19)
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- APPLICATIONS OF N6-SUBSTITUTED ADENOSINE DERIVATIVE AND N6-SUBSTITUTED ADENINE DERIVATIVE TO CALMING, HYPNOSES, CONVULSION RESISTANCE, EPILEPTIC RESISTANCE, PARKINSON DISEASE RESISTANCE, AND DEMENTIA PREVENTION AND TREATMENT
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PROBLEM TO BE SOLVED: To prepare analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. SOLUTION: The present invention relates to an N6-substituted adenosine derivative and an N6-substituted adenine derivative selected from the group consisting of specific compounds. The present invention also relates to a pharmaceutical composition at least comprising a therapeutically effective amount of the compounds and a pharmaceutically acceptable carrier. The invention further relates to the compounds used in preparation of analgesics, hypnotic agents, anticonvulsant agents, antiepileptics, antiparkinson drugs, dementia prophylactics, and health care food. COPYRIGHT: (C)2016,JPO&INPIT
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Paragraph 0240
(2018/10/27)
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- DNA binding and cleavage studies of copper(II) complexes with 2′-deoxyadenosine modified histidine moiety
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This work is focused on the study of DNA binding and cleavage properties of 2′-deoxyadenosines modified with ester/amide of histidine (his6dA ester, his6dA amide) and their copper(II) complexes. To determine the coordination mode of
- Borowska, Justyna,Sierant, Malgorzata,Sochacka, Elzbieta,Sanna, Daniele,Lodyga-Chruscinska, Elzbieta
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p. 989 - 1004
(2015/09/01)
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- Trifluoromethyl derivatives of canonical nucleosides: Synthesis and bioactivity studies
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The use of the system CF3SO2Na/tert-butyl- hydroperoxide (tert-ButOOH), recently reported for the efficient trifluoromethylation of a variety of heterocyclic aromatic compounds, has been here profitably exploited for the synthesis of 5-CF3-2′- deoxycytidine, 8-CF3-2′-deoxyadenosine, 8-CF 3-2′-deoxyguanosine and 8-CF3-inosine, regioselectively obtained in good to acceptable yields following a very simple protocol. The bioactivity of these modified nucleosides, and particularly of the novel 8-CF3-2′-deoxyguanosine and 8-CF3-inosine, has been evaluated on a panel of tumour and non-tumour cell lines in preliminary in vitro cytotoxicity assays.
- Musumeci, Domenica,Irace, Carlo,Santamaria, Rita,Montesarchio, Daniela
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supporting information
p. 1405 - 1410
(2013/10/08)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Paragraph 0493
(2013/03/26)
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- N6-SUBSTITUTED ADENOSINE DERIVATIVES, N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF
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The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.
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Page/Page column 116
(2012/11/06)
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- Impact of histidine residue on chelating ability of 2′- deoxyriboadenosine
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Copper(II) complexes with a new chelator-type nucleoside-histidine modified 2′-deoxyriboadenosine (N-[(9-β-D-2′-deoxyribofuranosylpurin-6- yl)-carbamoyl]histidine) were studied by potentiometric and spectroscopic (UV-visible, CD, EPR) techniques, in conju
- Lodyga-Chruscinska, Elzbieta,Oldziej, Stanislaw,Sochacka, Elzbieta,Korzycka, Karolina,Chruscinski, Longin,Micera, Giovanni,Sanna, Daniele,Turek, Monika,Pawlak, Justyna
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experimental part
p. 1212 - 1219
(2012/05/04)
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- RNA-cleaving 10-23 deoxyribozyme with a single amino acid-like functionality operates without metal ion cofactors
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A series of 10-23 deoxyribozymes (D2-D9) containing single amino-acid-bearing nucleosides (thr6dA, hisam6dA, hisam5dU and ncmnm5dU) at positions 4, 5, 8 or 15 of the catalytic core was obtained by chemical synthesis. The deoxyribozymes were screened for their catalytic efficiency, and in the presence of 1 mM Mg 2+ two of them, containing at position 8 either hisam5dU (D8) or ncmnm5dU (D9), were found to be RNA nucleases several times more active than their non-modified precursor. Moreover, in the magnesium-free TRIS or PIPES buffers, these enzymes were able to catalyze the cleavage of the phosphodiester bond located between the 5'-GpU-3' sequence of the complementary RNA substrate. The cleavage reaction proceeded with the highest efficiency at pH > 7.
- Smuga, Damian,Majchrzak, Kinga,Sochacka, Elzbieta,Nawrot, Barbara
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scheme or table
p. 934 - 948
(2010/08/05)
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- Synthesis and biological evaluation of nucleoside analogues having 6-chloropurine as anti-SARS-CoV agents
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Nucleoside analogues that have 6-chloropurine as the nucleobase were synthesized and evaluated for anti-SARS-CoV activity by plaque reduction and yield reduction assays in order to develop novel anti-SARS-CoV agents. Among these analogues, two compounds,
- Ikejiri, Masahiro,Saijo, Masayuki,Morikawa, Shigeru,Fukushi, Shuetsu,Mizutani, Tetsuya,Kurane, Ichiro,Maruyama, Tokumi
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p. 2470 - 2473
(2008/02/13)
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- Biomarkers for isocyanate exposure: Synthesis of isocyanate DNA adducts
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Isocyanates are important intermediates in industrial manufacturing. DNA adducts and protein adducts are important tools to biomonitor people exposed to xenobiotics. In the present work, the formation of DNA adducts deriving from 4-chlorophenyl isocyanate
- Beyerbach, Armin,Farmer, Peter B.,Sabbioni, Gabriele
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p. 1611 - 1618
(2008/09/20)
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- Nucleic acid related compounds. 127. Selective N-deacylation of N,O-peracylated nucleosides in superheated methanol
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Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath ≥ 105 °C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.
- Nowak, Ireneusz,Conda-Sheridan, Martin,Robins, Morris J.
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p. 7455 - 7458
(2007/10/03)
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- Lewis acid deprotection of silyl-protected oligonucleotides and base-sensitive oligonucleotide analogues
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a- a- a- Oligonucleotides protected with N-(trimethylsilylethoxycarbonyl) (Teoc) and P-(trimethylsilylethanol) (Tse) groups were synthesized and deprotected by a single ZnBr2 treatment. Teoc group stabilized dA against depurination. This strategy was applied to the synthesis of base-sensitive oligonucleotide prodrugs bearing S-acetyl-2-thioethyl (Sate) phosphotriesters.
- Ferreira, Fernando,Vasseur, Jean-Jacques,Morvan, Fran?ois
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p. 6287 - 6290
(2007/10/03)
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- Nucleosides, nucleotides and oligonucleotides containing enzymatically cleavable protecting groups
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Process for the production of oligonucleotides of formula II, in which the exocyclic amino groups of the bases adenine, guanine, cytosine, 7-deazaadenine and 7-deazaguanine carry N-phenylacetyl groups, are used for oligonucleotide synthesis, wherein in a first step a starting nucleotide is bound to a solid carrier, subsequently the desired oligonucleotide is synthesized by stepwise coupling with appropriately activated further monomeric nucleotide building blocks of the general formula I with the above-mentioned meanings, if desired, trivalent phosphorus is oxidized to pentavalent phosphorus during and after the synthesis, the oligonucleotide is cleaved from the carrier and the 5' protecting groups are cleaved off. The phenylacetyl functional groups that protect exocyclic NH2 groups of the bases can be cleaved off in a mild way with penicillin amidohydrolase (EC 3.5.1.11).
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- Molecular conformation of 2'-deoxy-3',5'-di-O-acetyl adenosine. Crystal structure and high resolution proton nuclear magnetic resonance investigations
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2'-Deoxy-3',5'-di-O-acetyl adenosine crystallizes in the orthorombic space group P212121, and the cell dimensions are a = 7.768(1) Angstroem, b = 12.890(1) Angstroem, c = 15.495(1) Angstroem; Z = 4 molecules per cell.Least-squares refinement converged at R = 0.054 for 1752 observed reflections.The adenine bases are linked via N6-H...N1 and N6-H...N7 hydrogen bonds, in such a way that infinite one-dimensional chains are formed.Comments are made on the fact that this structure is entirely different from the parallel dimer that was found for 3',5'-di-O-acetyl thymidine.Furthermore, the conformational preferences of the title compound in aqueous solution have been determined with 300- and 500-MHz 1H nmr.It is found that the X-ray structure and the solution conformation are essentially similar, except fot the C4'-C5' conformation, that isγ- in the solid state, and predominantly γ+ in solution.
- Koole, Leo H.,Buck, Henk M.,Kanters, Jan A.,Schouten, Arie
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p. 326 - 331
(2007/10/02)
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- THE p-NITROPHENYLETHYL (NPE) GROUP. A VERSATILE NEW BLOCKING GROUP FOR PHOSPHATE AND AGLYCONE PROTECTION IN NUCLEOSIDES AND NUCLEOTIDES
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The syntheses of new monomeric building blocks for oligonucleotide synthesis via the phosphotriester approach containing the p-nitrophenylethyl group for phosphate and aglycone protection are described.Blocking of the amide function in guanosines at O6 can be achieved by the Mitsunobu reaction forming the corresponding O6-p-nitrophenylethyl derivatives (4,5,10).Sugar-protected thymidine (16) and uridine (17) have been alkylated at O4 in an SN1-type reaction by p-nitrophenylethyl iodide-silver carbonate in benzene to form the O4-p-nitrophenylethyl derivatives (18,19).Protection of the amino group in 2'-deoxycytidine (25) and cytidine (26) can be performed directly by 1-(p-nitrophenylethoxycarbonyl)-benzotriazole in DMF to obtain the corresponding carbamates (27,28) as a new type of N4-acylated cytidine derivative. p-Nitrophenylethoxycarbonylation of the amino group in 2'-deoxyadenosine (33) and adenosine (34) requires previous sugar protection by acyl or silyl groups and can then be achieved by p-nitrophenylethyl chloroformate or better by 1-methyl-3-p-nitrophenylethoxycarbonylimidazolium chloride to form N6-p-nitrophenylethoxycarbonyladenosines (38,39,40,42).The various p-nitrophenylethyl blocking groups are stable under mild hydrolytic conditions (e.g. ammonia and triethylamine) but can be cleaved selectively by DBU or DBN in aprotic solvents. 5'-O-Monomethoxytritylation (12,29,43) as well as phosphorylations at the 3'-OH group can be effected to give the corresponding 3'-(2,5-dichlorophenyl,p-nitrophenylethyl)-phosphotriesters (13,22,30,44) also in high yields.Oximate cleavage of the latter compounds to the phosphodiesters (14,24,32,46) and detritylation to the 5'-unblocked phosphotriesters (15,23,31,45) do not affect the aglycone protecting groups, thereby demonstrating their general versatility.The newly synthesized compounds have been characterized on the basis of their elementary analyses (C,N,H), and UV- and 1H-HMR-spectra.
- Himmelsbach, Frank,Schulz, Bernd S.,Trichtinger, Thomas,Charubala, Ramamurthy,Pfleiderer, Wolfgang
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- THE USE OF THE p-NITROPHENYLETHOXYCARBONYL GROUP FOR AMINO PROTECTION IN CYTIDINE AND ADENOSINE CHEMISTRY
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Amino protection in 2'-deoxycytidine (1) and cytidine (2) as well as in 2'-deoxyadenosine (8) and adenosine (9) respectively can be achieved by the new reagents 1-(p-nitrophenylethoxycarbonyl)-benzotriazole (3) and 1-methyl-3-(p-nitrophenylethoxycarbonyl)-imidazolium chloride (7) to from the corresponding carbamates (4, 5, 13, 14) in high yields.
- Himmelsbach, Frank,Pfleiderer, Wolfgang
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p. 3583 - 3586
(2007/10/02)
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