Direct synthesis of 5'-nucleotides using glycosylation reaction

Gulyaeva, Irina V.; Efimtseva, Ekaterina V.; Rodionov, Andrei A.; Ermolinsky, Boris S.; Mikhailov, Sergey N.

doi:10.1135/css200205312

Cited by 2 publications

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“…According to massspectrometry only one p-nitrophenylethyl group was cleaved using 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) or even stronger bases. It was shown previously that the deprotection of NPE triester derivatives of 5 -nucleotides with 0.5 M DBU in pyridine was incomplete after 5 days [101].…”

Section: Oligonucleotides Containing Disac-charide Nucleosidesmentioning

confidence: 98%

Disaccharide Nucleosides and their Incorporation into Oligonucleotides

Efimtseva¹,

Kulikova²,

Mikhailov³

2007

COC

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The review summarizes structural features, biological activity and synthetic methods of disaccharide nucleosides. In the first part the structures of natural disaccharide nucleosides are presented. The consequent part deals with general methods of synthesis of these compounds -formation of new N-and O-glycosidic bonds. Recent achievements in the preparation of disaccharide nucleosides from natural nucleosides are discussed. The last part is devoted to the synthesis and properties of oligonucleotides containing disaccharide nucleosides.Disaccharide nucleosides belong to an important group of natural compounds forming poly(ADP-ribose) and found in tRNA, antibiotics, and other physiologically active compounds. To date about a hundred disaccharide nucleoside and related derivatives have been isolated from various natural sources. These compounds contain an extra carbohydrate residue linked to one of the nucleoside hydroxyl groups via an O-glycosidic bond. The presence of a disaccharide residue and a heterocyclic base makes their properties similar to those of carbohydrates and nucleosides. These compounds manifest a broad spectrum of biological (including antibacterial, fungicidal, herbicidal, antitumour and antiviral) activities. The review by Lerner [1] published in 1991 provides a detailed description of the structures of disaccharide nucleoside antibiotics and the approaches to their synthesis. Some of the published data on the synthesis of complex nucleoside antibiotics were summarized by Knapp [2]. Since that time, many new publications devoted to this problem have appeared in the current literature. In our recent publiccations physicochemical properties [3], structure and general synthetic approaches to the synthesis [4] of disaccharide nucleosides were reviewed. Here we describe structural peculiarities of disaccharide nucleosides and summarize our recent data on their synthesis and incorporation into oligonucleotides (ONs). NATURAL DISACCHARIDE NUCLEOSIDESThe structures of disaccharide nucleosides are extremely diverse [5,6] and their elucidation is a rather complicated task. In addition to a heterocyclic base and two mono-saccharide residues, these compounds contain various functional substituents, such as acyl and alkyl groups as well as phosphate and sulfate residues, fatty acids, amino acids, peptides and additional sugars. Their degradation by acid and alkaline hydrolysis or methanolysis, periodate oxidation and subsequent reduction yields fragments the structures of which can be established by physicochemical methods. At present, the structures of many complex antibiotics are determined mainly by NMR spectroscopy and mass spectrometry.According to their structure natural disaccharide nucleosides may be divided into three main groups. Disaccharide nucleosides belonging to the first two groups contain natural purine nucleoside. In the first group additional ribofuranosyl residue is attached via O-glycosidic bond to the adenosine or guanosine. Most of these derivatives were found in biopolymers. 2 (3 )-O-...

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Section: Oligonucleotides Containing Disac-charide Nucleosidesmentioning

confidence: 98%

Disaccharide Nucleosides and their Incorporation into Oligonucleotides

Efimtseva¹,

Kulikova²,

Mikhailov³

2007

COC

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“…According to mass spectrometry, only one npe group was cleaved with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or even stronger bases. It was shown previously that the deprotection of some triester derivatives of 5'-nucleotides with 0.5m DBU in pyridine was incomplete after five days [27]. overall yields.…”

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confidence: 97%

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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Direct synthesis of 5'-nucleotides using glycosylation reaction

Cited by 2 publications

References 0 publications

Disaccharide Nucleosides and their Incorporation into Oligonucleotides

Disaccharide Nucleosides and their Incorporation into Oligonucleotides

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

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