- A new and convenient approach for the preparation of β-cyanoethyl protected trinucleotide phosphoramidites
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Herein we report a convenient approach for the preparation of fully protected trinucleotide synthons to be used for the synthesis of gene libraries. The trinucleotide synthons bear β-cyanoethyl groups at the phosphate residues, and thus can be used in standard oligonucleotide synthesis without additional steps for deprotection and work-up.
- Janczyk, Matthaeus,Appel, Bettina,Springstubbe, Danilo,Fritz, Hans-Joachim,Mueller, Sabine
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supporting information; experimental part
p. 1510 - 1513
(2012/03/22)
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- Exploring the synthesis of masked phosphoramido 6-vinylcytidine derivatives as building blocks for cross-linking oligonucleotides
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In the present work the synthesis of building blocks (2a,b), bearing a masked form of the reactive vinyl group bound to the C-6 position of a cytidine derivative, has been studied. The understanding of byproduct formation together with conformational considerations let us to plan a straightforward approach for the synthesis of the target compounds.
- Radi, Marco,Spinosa, Raffaella,Parlato, Maria Cristina,Corelli, Federico,Botta, Maurizio
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p. 151 - 166
(2008/02/09)
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- Metallic salt of N4-acylcytidine derivatives, and a method for producing N4-acylcytidine derivatives using the same
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The present invention provides a method for producing a high purity N4-acylcytidine derivative. More specially, the invention provides a compound represented by the formula (1): wherein R1 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a halogen atom; R2 is a hydrogen atom, an alkoxyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms with a substituent, or a halogen atom; R3 represents a methyl group or a phenyl group; and M represents a positive ion of an alkali metal or an alkaline earth metal, and a compound represented by the formula (2): wherein R1, R2, and R3 are as defined above, produced by using the compound represented by the formula (1).
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Page/Page column 6
(2010/02/13)
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- Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides
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An unique set of 5′-O- and 3′-O-phosphonomethyl derivatives of four natural 2′-deoxyribonucleosides, 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine, 5′-O- and 2′-O-phosphonomethyl derivatives of 1-(3-deoxy-β-D-erythro-pentofuranosyl)thymine, and 1-(3-deoxy-β-D- threo-pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4-methoxy-1-oxido-2-pyridylmethyl ester group, serving also as an intramolecular catalyst in the coupling step.
- Rejman, Dominik,Masojidkova, Milena,Rosenberg, Ivan
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p. 1683 - 1705
(2007/10/03)
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- Method for purifying protected 2'-deoxycytidines and hydrated crystals thereof
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A protected 2′-deoxycytidine is purified by precipitating the protected 2′-deoxycytidine represented by general formula (3) in the form of a hydrated crystal from a solution containing the protected 2′-deoxycytidine and water, and by recovering the protected 2′-deoxycytidine: wherein R1 represents a 4-methoxytrityl, 4,4′-dimethoxytrityl, or triphenylmethyl group; and B1 represents a cytosine group having a protected amino group. The compound represented by general formula (3) is, in particular, a protected 2′-deoxycytidine represented by formula (4): The 2′-deoxycytidine is used as a raw material for antisense DNA.
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- A mild and efficient method for the preparation of 5'-dimethoxytrityl- 2'-deoxynucleoside using poly(4-vinylpyridine)costyrene
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5'-O-4,4'-Dimethoxytrityl-2'-deoxynucleosides have been synthesized in high yield by the reaction of 2'-deoxynucleosides with 4, 4'-dimethoxytrityl chloride in acetonitrile using poly (4-vinylpyridine)-costyrene(styrene 10%).
- Karalkar, Nilesh B.,Akerkar, Vinayak G.,Salunkhe, Manikrao M.
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p. 370 - 371
(2007/10/03)
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- Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'α-C-branched-chain sugar pyrimidine nucleosides
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A series of 4'α-C-branched-chain pyrimidine nucleosides was synthesized from 2'-deoxycytidine or uridine. In the 2'-deoxycytidine series, the substituent at the 4'α-position affected cytotoxicity against L1210 mouse leukemic cells in vitro in the order Me (23) > CN (22)> C≡CH (21) > CH=CH2 (19) > Et (24) > CH=CHCl (20). However, uridine and cytidine derivatives with ethynyl and cyano groups at the 4'α-position did not show any cytotoxicity. The antiviral activities of these nucleosides against HSV-1, HSV-2, and HIV- 1 in vitro were also examined. Compounds 22 and 23 showed antiviral activities against HSV-1 and HSV-2 without showing significant toxicity to the host cells (MRC-5 cells). Although almost all of the nucleosides showed anti-HIV-1 activities, they were also cytotoxic to the host cells (MT-4).
- Nomura, Makoto,Shuto, Satoshi,Tanaka, Motohiro,Sasaki, Takuma,Mori, Shuichi,Shigeta, Shiro,Matsuda, Akira
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p. 2901 - 2908
(2007/10/03)
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- Nucleoside recovery in DNA and RNA synthesis
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Nucleoside phosphoramidites and H-phosphonate diesters can be converted to nucleosides under mild conditions and in high yields by reaction with polyhydroxy alcohols.
- Wang, Weimin,Song, Quanlai,Jones, Roger A.
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p. 8971 - 8974
(2007/10/03)
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- Dephosphonylation of protected deoxynucleoside and oligodeoxynucleotide H-phosphonates
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The conversion of four 5'-O-(4,4'-dimethoxytrityl)-2'- deoxyribonucleoside 3'-H-phosphonates 1 (B=4, 5, 6 and 7) into their partially-protected nucleoside precursors 3 (B=4, 5, 6 and 7, respectively) in good isolated yields is described. The procedure used is also suitable for the dephosphonylation of protected oligonucleotide H-phosphonate blocks.
- Reese, Colin B.,Visintin, Cristina
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p. 6477 - 6480
(2007/10/03)
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- Synthesis and characterization of phosphate-modified DNA-dimers with fluorine as an uncharged ligand
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The potential of the dinucleosidylphosphorofluoridates dCpFdG and dApFdT is described. Side products of the phosphoramidite coupling reaction are synthesized and characterized by 31P-NM]R-spectroscopy.
- Lehmann, Thomas J.,Eisenhardt, Stefan,Engels, Joachim W.
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p. 815 - 820
(2007/10/03)
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- Nucleoside 5'-methylene phosphonates
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Novel oligonucleotides analogs and nucleoside analogs as well as methods for their synthesis are described. The oligonucleotides are useful in diagnostic and therapeutic applications. The oligonucleotides are stable to nuclease degradation.
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- Facile methods to recycle nucleosides during solid phase synthesis of oligonucleotides
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Solid phase syntheses of oligonucleotides, using nucleoside phosphoramidites or methylphosphonamidites require a large excess of nucleoside monomers over the hydroxy functions of the growig oligonucleotide chain bound onto the solid phase. The outlined method allows to recover the excess nucleosides. All the protective groups on the sugar and the nucleobase of the monomers are maintained throughout the recycling process.
- Brill, Wolfgang K.-D.
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p. 3041 - 3044
(2007/10/02)
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- Simplified Liquid-Phase Preparation of Four Decadeoxyribonucleotides and their Preliminary Spectroscopic Characterization
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Four self-complementary decadeoxyribonucleotides, dApTpApTpApTpApTpApT,dApTpApTpCpGpApTpApT, dApTpApTpGpCpApTpApT and dApApApApApTpTpTpTpT, were chemically synthesized by the phosphotriester procedure.Efforts were concentrated on keeping the procedure as simple as possible, concomitant with obtaining high-purity products at each step of the process.The decamers were elaborated from the 3'-end, starting with a 3'-O-benzoylated monomer according to the scheme: monomer + monomer -> dimer + dimer -> tetramer + dimer -> hexamer + tetramer -> decamer.Putity of intermediates and of the fully blocked decamers were monitored by chromatography and by 300-MHz 1H-NMR. spectroscopy.The deblocked decadeoxyribonucleotides were characterized by their UV., CD., and 1H-NMR. spectra.
- Denny, William A.,Leupin, Werner,Kearns, David R.
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p. 2372 - 2393
(2007/10/02)
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- Transient Protection: Efficient One-Flask Syntheses of Protected Deoxynucleosides
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Application of the concept of transient protection to the synthesis of protected deoxynucleosides is described.The deoxynucleosides are first treated with trimethylchlorosilane in pyridine for protection of the hydroxyl groups, and then immediately reacted with an acylating agent - benzoyl chloride for 1a and 1b and isobutyric anhydride for 1c - to effect N-acylation.Hydrolysis of the trimethylsilyl groups takes a few hours in aqueous pyridine or a few minutes with dilute ammonia.The ammonia also effects selective hydrolysis of the initially formed N,N-dibenzoyldeoxyadenosine derivative (3a) to the desired N-benzoyldeoxyadenosine (4a).This one-flask procedure gives crystalline N-acyl deoxynucleosides 4a and 4b in 95percent yield and 4c in 75percent yield, in only a few hours.The 5'-O-dimethoxytrityl deoxynucleosides 8a and 8b are also obtained in a one-flask procedure by initial reaction of the deoxynucleosides with 4,4'-dimethoxytrityl chloride, followed by treatment with trimethylchlorosilane and then benzoyl chloride.Although with deoxycytidine some of the 4-N,5'-O-bis(dimethoxytrityl) derivative (5c) is formed, benzoyl chloride effects conversion to the 4-N-benzoyl derivative (7b).After simple purification by flash chromatography 8a and 8b are each obtained in 80-90percent overall yield from 1a or 1b.
- Ti, G. S.,Gaffney, B. L.,Jones, R. A.
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p. 1316 - 1319
(2007/10/02)
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