An Efficient Synthesis and Physico-Chemical Properties OF 2'-O-d-Ribofuranosylnuleosides, Minor tRNA Components

Mikhailov, Sergey N.; Efimtseva, Ekaterina V.; Gurskaya, G. V.; Fomitcheva, Marina V.; Meshkov, S. V.; Zavodnik, V. E.; Bruyn, André De; Janssen, G.; Rozenski, Jef; Herdewijn, Piet

doi:10.1080/07328309708006511

Cited by 42 publications

(30 citation statements)

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“…) was performed according to previously described procedures. It consists in the condensation of N,3'-O,5'-O-protected ribonucleosides 1 and 1-O-acetyl-2,3,5-tri-O-benzoyl-b-d-ribofuranose in the presence of SnCl 4 in dichloroethane [8], conditions originally proposed for the preparation of alkyl b-dribofuranosides [13]. Sugars that were successfully used in this reaction are peracylated d-(and l-) arabinofuranoses, d-ribopyranose, and d-erythrofuranose.…”

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“…The synthesis of disaccharide nucleoside 2a was described previously [8]. Analogous condensation of 1 with an excess of 1-O-acetyl-2,3,5-tri-O-benzoyl-d-or l-arabinofuranose [14] in the presence of SnCl 4 for 16 h at 08 gave disaccharides 2b and 2c in good yields.…”

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confidence: 99%

“…Only for the ribopyranosyl derivative 2d is J(1'',2'') 2.3 Hz. The assignments of the protons and C-atoms in the 1 H-and 13 C-NMR spectra were made in analogy with related disaccharide nucleosides [8] [16].…”

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Oligonucleotides Containing Disaccharide Nucleosides

Efimtseva

Bobkov

Mikhailov

et al. 2001

HCA

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Disaccharide nucleosides with 2'-O-(d-arabinofuranosyl), 2'-O-(l-arabinofuranosyl), 2'-O-(d-ribopyranosyl), 2'-O-(d-erythrofuranosyl), and 2'-O-(5-azido-5-deoxy-d-ribofuranosyl) substituents were synthesized. These modified nucleosides were incorporated into oligonucleotides (see Table). Single substitution resulted in a DT m of 0.5 to À 1.48 for DNA/RNA and a DT m of À 0.8 to À 4.78 for DNA/DNA duplexes. These disaccharide nucleosides can be well accommodated in RNA/DNA duplexes, and the presence of a NH 2 ÀC(5'') group has a beneficial effect on duplex stability.

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Oligonucleotides Containing Disaccharide Nucleosides

Efimtseva

Bobkov

Mikhailov

et al. 2001

HCA

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“…Tetraisopropyldisiloxane-1,3-diyl (TIPDS) group developed by Markiewicz 1,2 is widely used for simultaneous protection of 3′,5′-hydroxyl groups in ribonucleosides and subsequent manipulation with 2'-OH group of ribonucleosides: deoxygenation, 3,4 oxidation, 5 alkylation, [6][7][8][9][10] glycosylation, [11][12][13][14][15][16] protection, 17-21 preparation of 2'-amino-2'-deoxynuclesides, 22,23 and so on. This group may be considered as one of the most popular and useful protecting group in the field of nucleoside chemistry.…”

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Effective isomerization of 3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl)nucleosides in the presence of trimethylsilyl trifluoromethanesulfonate

Kulikova¹,

Muradova²,

Mikhailov³

2008

Arkivoc

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Trimethylsilyl trifluoromethanesulfonate catalyze effective isomerization of 3′,5′-O-(tetraisopropyldisiloxane-1,3-diyl)nucleosides (1) in 1,2-dicloroethane at 0°C into 2′,3′-O-(tetraisopropyldisiloxane-1,3-diyl)-derivatives (2), which can be obtained in 55-90% yields. On the other hand nucleosides 1 were found to be stable in the presence of tin tetrachloride. Only in the case of uridine derivative 1a a substantial amount of isomerization product 2a was formed.

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“…Most of the chemical shifts and coupling constants may be calculated directly from NMR spectra. In some cases, comparison with the published spectra of disaccharide nucleosides [25] [32], and double-resonance, 1 H, 13 C-correlation and COSY spectra were used for the assignment. The chemical incorporation of the phosphorylated disaccharide was tested on the Tloop sequence of yeast initiator tRNA Met [14] [33] (A in Fig.…”

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Synthesis of RNA ContainingO-β-D-Ribofuranosyl-(1″2′)-adenosine-5″-phosphate and 1-Methyladenosine, Minor Components of tRNA

Mikhailov

Efimtseva

Rodionov

et al. 2005

C&B

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tRNA is best known for its function as amino acid carrier in the translation process, using the anticodon loop in the recognition process with mRNA. However, the impact of tRNA on cell function is much wider, and mutations in tRNA can lead to a broad range of diseases. Although the cloverleaf structure of tRNA is wellknown based on X-ray-diffraction studies, little is known about the dynamics of this fold, the way structural dynamics of tRNA is influenced by the modified nucleotides present in tRNA, and their influence on the recognition of tRNA by synthetases, ribosomes, and other biomolecules. One of the reasons for this is the lack of good synthetic methods to incorporate modified nucleotides in tRNA so that larger amounts become available for NMR studies. Except of 2'-O-methylated nucleosides, only one other sugar-modified nucleoside is present in tRNA, i.e., 2'-O-b-d-ribofuranosyl nucleosides. The T loop of tRNA often contains charged modified nucleosides, of which 1-methyladenosine and phosphorylated disaccharide nucleosides are striking examples. A protecting-group strategy was developed to introduce 1-methyladenosine and 5''-O-phoshorylated 2'-O-(b-dribofuranosyl)-b-d-ribofuranosyladenine in the same RNA fragment. The phosphorylation of the disaccharide nucleoside was performed after the assembly of the RNA on solid support. The modified RNA was characterized by mass-spectrometry analysis from the RNase T1 digestion fragments. The successful synthesis of this T loop of the tRNA of Schizosaccharomyces pombe initiator tRNA Met will be followed by its structural analysis by NMR and by studies on the influence of these modified nucleotides on dynamic interactions within the complete tRNA.

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An Efficient Synthesis and Physico-Chemical Properties OF 2'-O-d-Ribofuranosylnuleosides, Minor tRNA Components

Abstract: A high yield preparation of 9-(2-O-~-~-ribofbranosyl-~-~-ribofUranosyl)adenine, guanine-and the pyrimidine analogs (cytosine, thymine and uracil base moiety) has been achieved, and the conformational properties of the ring systems were investigated using NMR spectroscopy and X-ray.

Cited by 42 publications

References 4 publications

Oligonucleotides Containing Disaccharide Nucleosides

Oligonucleotides Containing Disaccharide Nucleosides

Effective isomerization of 3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl)nucleosides in the presence of trimethylsilyl trifluoromethanesulfonate

Synthesis of RNA ContainingO-β-D-Ribofuranosyl-(1″2′)-adenosine-5″-phosphate and 1-Methyladenosine, Minor Components of tRNA

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