- BICYCLIC PEPTIDE LIGAND STING CONJUGATES AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 00548
(2020/08/28)
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- Tritylation of alcohols under mild conditions without using silver salts
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Secondary alcohols were conveniently tritylated under mild conditions within a short running time with tritylium trifluoroacetate generated in situ from trityl alcohols and trifluoroacetic anhydride. No expensive silver salts were needed for the reactions. Four secondary alcohols were tritylated with both mono- and dimethoxy trityl alcohols giving good to excellent isolated yields. The reaction was also tested on four nucleoside derivatives that have primary alcohols. Satisfactory results were also obtained.
- Shahsavari, Shahien,Chen, Jinsen,Wigstrom, Travis,Gooding, James,Gauronskas, Alexander,Fang, Shiyue
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p. 3877 - 3880
(2016/08/02)
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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 5'-protected 2'-deoxypurine nucleosides
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A method for efficiently purifying 5' protected 2'-deoxypurine nucleosides, efficient production of which has previously been difficult. Impurities can be separated by obtaining the 5' protected 2'-deoxypurine nucleoside as an inclusion crystal including a solvent such as that having a nitrile structure in order to purify the 5' protected 2'-deoxypurine nucleoside at a high purity. This invention enables synthesis of highly purified protected deoxypurine nucleosides easily on a large scale, which has previously been performed by column chromatography method.
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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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- 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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- Synthesis and Selective Cleavage of an Oligodeoxynucleotide Containing a Bridged Non-Chiral Internucleotide 3'-Phosphoramidate Linkage
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A self complementary oligodeoxynucleotide dodecamer containing an achiral bridged 3'-phosphoramidate linkage 3'-NH-P-O-5' has been prepared using the solid phase phosphoramidate procedure.Cleavage of the P-N bond can be accomplished selectively by mild acidolysis.
- Mag, Matthias,Schmidt, Rainer,Engels, Joachim W.
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p. 7319 - 7323
(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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- Synthesis and Designation of the Diastereomeric Forms of Fully Protected 2'-Deoxyadenylyl-(3'-5')-2'-deoxyadenosine
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The synthesis of the fully protected 2'-deoxyadenylyl-(3'-5')-2'-deoxyadenosine 3a is reported.Due to the chiral phosphotriester group 3a exists in two diasteromeric forms (3aA and 3aB) which could be distinguished by TLC and HPLC as well as 1H and 31P NMR spectroscopy.The absolute configuration as RP (3aA) and SP (3aB) is proposed on the basis of NMR data and chromatographic properties in combination with space filling models.
- Michels, Winfried,Schlimme, Eckhard
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p. 1398 - 1402
(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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