Disaccharide nucleosides

Abstract

Structural features and biological properties of naturalStructural features and biological properties of natural disaccharide nucleosides and related compounds are considered. disaccharide nucleosides and related compounds are considered. The main methods for the synthesis of these compounds are The main methods for the synthesis of these compounds are described and their advantages and disadvantages are discussed. described and their advantages and disadvantages are discussed. These methods include condensations of a protected disaccharide These methods include condensations of a protected disaccharide with a heterocyclic base or of a protected nucleoside with an with a heterocyclic base or of a protected nucleoside with an activated monosaccharide. The bibliography includes 172 refer-activated monosaccharide. The bibliography includes 172 references ences. .

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

“…We have also investigated the isomerization of 1 in the presence of tin tetrachloride, which is widely used in glycosylation reactions. [28][29][30] From Table 2 it can be seen that only in the case of uridine derivative 1a a substantial amount of 2a and decomposition products were formed and the isomerization is faster at room temperature (entries 11-13). These results confirmed the above mentioned instability of uridine derivative 1a in the presence of this catalyst.…”

2-Position Base-Modified Analogues of Adenophostin A as High-Affinity Agonists of the d-myo-Inositol Trisphosphate Receptor: In Vitro Evaluation and Molecular Modeling

“…12 We 13 and others 14 have used this strategy successfully for the synthesis of various AdA analogues via Vorbrüggen condensation of an appropriate disaccharide with silylated nucleobase. However, Vorbrüggen condensation of guanine (or its derivatives) with acylated sugars is known 15 to form a mixture of N-7 and N-9 regioisomers, even under thermodynamic control, and hence is not suitable for synthetic purposes.…”

Poly(ADP-ribose): From chemical synthesis to drug design

“…9,10 Subsequent enzymatic dephosphorylation of compound 1 by alkaline phosphatase led to corresponding disaccharide nucleoside 3. 8,9,11 Compounds 2 and 4 represent the core motif of PAR branching. The common feature of compounds 1-4 is the presence of a(1 ?…”

“…To date about a hundred disaccharide nucleosides and related derivatives have been isolated from various natural sources. 2,8,11,33,34 Natural disaccharide nucleosides can be divided into three main groups according to their structure. In the first group additional ribofuranosyl residue is attached via O-glycosidic bond to adenosine or guanosine.…”

“…Native PAR molecules consist of more than 200-300 monomeric units, in which linear segments of 20-50 units alternate with branched motifs. 1,2,8 The chemical structure of PAR was determined by regiospecific enzymatic hydrolysis of the pyrophosphate bonds by snake venom phosphodiesterase with formation of disaccharide nucleotide 1 and trisaccharide nucleotide 2. Their structures were determined by NMR spectroscopy.…”