- 4′-Epi-DNA: A DNA Mimic Containing 4′-hydroxymethyl-α-l-Xylo-Thymidine with Compact Backbone like RNA
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Synthesis of C4′-epi-DNA containing 3′→ 5″ linkages is reported for the first time. Crystal structure study of the monomer indicated that though the dihedral angle O3′-C3′-C4′-C5″ in this case would be like in RNA, the sugar conformation would remain like that in DNA. The study of the effect of this backbone configuration in DNA with respect to its binding to cDNA and RNA is reported in this note.
- Bagmare, Seema,Puranik, Vedavati G.,Fernandes, Moneesha,Kumar, Vaijayanti A.
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p. 445 - 458
(2016/09/04)
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- Synthesis of covalently linked parallel and antiparallel DNA duplexes containing the metal-mediated base pairs T-Hg(ii)-T and C-Ag(i)-C
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DNA duplexes fixed in anti-parallel and parallel orientations by introducing covalent linkages have been synthesized and metal ions, Hg(ii) and Ag(i), were incorporated into pyrimidine-pyrimidine base pairs.
- Ono, Takashi,Yoshida, Kyohei,Saotome, Yuko,Sakabe, Rei,Okamoto, Itaru,Ono, Akira
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p. 1542 - 1544
(2011/03/22)
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- A new reagent system for efficient silylation of alcohols: Silyl chloride-N-methylimidazole-iodine
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It was found that reactions of alcohols with silyl chlorides in the presence of N-methylimidazole were significantly accelerated by the added iodine, and on this basis a general, and high yielding method for efficient silylation of primary, secondary, and
- Bartoszewicz, Agnieszka,Kalek, Marcin,Nilsson, Johan,Hiresova, Renata,Stawinski, Jacek
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- Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies
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An efficient silylating system for 1°, 2°, and 3° alcohols, consisting of a silyl chloride/N-methylimidazole/iodine, was developed. Synthetic and mechanistic aspects of this new reagent system, and particularly the role of iodine were investigated in detail using 1H NMR spectroscopy.
- Bartoszewicz, Agnieszka,Kalek, Marcin,Stawinski, Jacek
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p. 8843 - 8850
(2008/12/21)
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- 2-(Phenylthio)ethyl as a novel two-stage base protecting group for thymidine analogues
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2-(Phenylthio)ethyl is here proposed for temporary masking the thymine residue in the synthesis of sugar modified thymidine derivatives. This protection has been devised as a 'two-stage' system. The 2-(phenylthio)ethyl residue can be easily and regiospecifically inserted at the N3-position of the pyrimidine by a Mitsunobu reaction with 2-(phenylthio)ethanol and is perfectly stable also to strongly basic conditions. This allowed us to selectively achieve O-alkylation of the ribose moieties in satisfactory yields, avoiding undesired base alkylations. After oxidation of the thioether to sulfone, the thymine protecting group can be totally removed, by a β-elimination mechanism, upon the same basic treatment required for the final deprotection and detachment of oligonucleotides from the support in solid-phase synthesis protocols. Georg Thieme Verlag Stuttgart.
- D'Onofrio, Jennifer,De Napoli, Lorenzo,Di Fabio, Giovanni,Montesarchio, Daniela
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p. 845 - 848
(2007/10/03)
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- Method for purifying 5' -protected thymidines and novel derivatives thereof
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This invention provides a method for efficiently purifying 5′-protected thymidines which cannot be efficiently purified by the prior art. Impurities can be separated by obtaining crystals including a carbonyl-containing solvent to provide a highly pure 5′
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- A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3'-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and - peptide conjugates
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A new method for synthesis of 3'-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base- labile structures such as oligoDNA-OPO(OH)OCH2CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, 5'TGTCGACACCCAATT3'-OPO(OH)OCH2CH(NH2)COOH, and a oligonucleotide-peptide conjugate, 5'TGTCGACACCCAATT3'- OPO(OH)OCH2CH(NH2)CONHCH2COOH, have been obtained in high purity.
- Sakakura, Akira,Hayakawa, Yoshihiro,Harada, Hitoshi,Hirose, Masaaki,Noyori, Ryoji
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p. 4359 - 4362
(2007/10/03)
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- A simple and convenient method for the deprotection of tetrahydropyranyl ether using iodine in methanol
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A simple and efficient method for the deprotection of tetrahydropyranyl and 4,4'-dimethoxytrityl ethers using iodine in methanol is described.
- Ramasamy, Kanda S.,Bandaru, Rajanikanth,Averett, Devron
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p. 2881 - 2894
(2007/10/03)
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- Synthesis of 3'-azido-3'-deoxythymidine-terminated oligonucleotide
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A method of completely chemical synthesis of 3'-azido-3'- deoxythymidine-terminated oligonucleotides via 5'-H-phosphonate of AZT is described.
- Esipov, Dmitriy S.,Esipova, Olga V.,Korobko, Vyacheslav G.
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p. 1697 - 1704
(2007/10/03)
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- Synthesis and evaluation of oligodeoxynucleotides containing 4'-C-substituted thymidines
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4'-C-Hydroxymethylthymidine was converted to 4'-C-methoxymethylthymidine and 4'-C-aminomethylthymidine, which were incorporated into oligodeoxynucleotides by phosphoramidite chemistry. The modified oligonucleotides exhibit excellent hybridization and significant improvement in stability to snake venom phosphodiesterase.
- Wang, Guangyi,Seifert, Wilfried E.
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p. 6515 - 6518
(2007/10/03)
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