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Synthesis of nucleosides involves the coupling of a nucleophilic, heterocyclic base with an electrophilic sugar. The silyl-Hilbert-Johnson (or Vorbrüggen) reaction, which employs silylated heterocyclic bases and electrophilic sugar derivatives in the presence of a Lewis acid, is the most common method for forming nucleosides in this manner.
Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group. A nucleoside consists simply of a nucleobase (also termed a nitrogenous base) and a five-carbon sugar ( ribose or 2'-deoxyribose) whereas a nucleotide is composed of a nucleobase, a five-carbon sugar, and one or more phosphate groups.
Nucleoside analogues are nucleosides that are structurally similar (analogous) to the nucleosides used in DNA and RNA synthesis. [41] Once these nucleoside analogues enter a cell, they can become phosphorylated by a viral enzyme.
Use in artificial nucleotide synthesis [ edit ] 1- O -Acetyl-2,3,5-tri- O -benzoyl-β- D -ribofuranose is further reacted with trimethylsilyl trifluoromethanesulfonate (TMSOTf) under the silyl-Hilbert–Johnson reaction and deprotected by an acid or base to form a pure artificial nucleotide.
Nucleotide salvage pathways are used to recover bases and nucleosides that are formed during degradation of RNA and DNA. This is important in some organs because some tissues cannot undergo de novo synthesis. The salvaged products can then be converted back into nucleotides.
Oligonucleotide synthesis is the chemical synthesis of relatively short fragments of nucleic acids with defined chemical structure ().The technique is extremely useful in current laboratory practice because it provides a rapid and inexpensive access to custom-made oligonucleotides of the desired sequence.
Pyrimidine nucleosides include cytidine, uridine, and thymidine. [4] The synthesis of any pyrimidine nucleotide begins with the formation of uridine. This reaction requires aspartate, glutamine, bicarbonate, and 2 ATP molecules (to provide energy), as well as PRPP which provides ribose-monophosphate. Unlike in purine synthesis, the sugar ...
To avoid undesired side reactions, reactive hydroxy and exocyclic amino groups present in natural or synthetic nucleosides are appropriately protected. As long as a nucleoside analog contains at least one hydroxy group, the use of the appropriate protecting strategy allows one to convert that to the respective phosphoramidite and to incorporate ...