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Synthesis of nucleosides information


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.[1]

  1. ^ Vorbrüggen, H.; Ruh-Polenz, C. Org. React. 1999, 55, 1. doi:10.1002/0471264180.or055.01

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Synthesis of nucleosides

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presence of a Lewis acid, is the most common method for forming nucleosides in this manner. Nucleosides are typically synthesized through the coupling of a nucleophilic...

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Nucleoside

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Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group. A nucleoside consists simply of a nucleobase (also termed...

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Nucleoside triphosphate

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infections. Nucleoside analogues are nucleosides that are structurally similar (analogous) to the nucleosides used in DNA and RNA synthesis. Once these...

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Nucleotide

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showed how pyrimidine nucleosides can be synthesized from small molecules and ribose, driven solely by wet-dry cycles. Purine nucleosides can be synthesized...

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Carbocyclic nucleoside

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approaches used in the synthesis of carbocyclic nucleosides. Linear approaches to chiral carbocyclic nucleosides 2 rely on the construction of the heterocyclic...

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Oligonucleotide synthesis

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(1997). "Ultrafast Cleavage and Deprotection of Oligonucleotides Synthesis and Use of CAc Derivatives". Nucleosides & Nucleotides. 16 (7): 1589–1598. doi:10...

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Purine

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purine bases are guanine (G) and adenine (A) which form corresponding nucleosides-deoxyribonucleosides (deoxyguanosine and deoxyadenosine) with deoxyribose...

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Methylthiouracil

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1002/jlac.18862360102. Vorbrüggen H, Ruh-Pohlenz C (April 2004). "Synthesis of nucleosides". Organic reactions. 55: 1–630. doi:10.1002/0471264180.or055.01...

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Nucleoside phosphoramidite

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Nucleoside phosphoramidites are derivatives of natural or synthetic nucleosides. They are used to synthesize oligonucleotides, relatively short fragments...

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Dimethoxytrityl

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group widely used for protection of the 5'-hydroxy group in nucleosides, particularly in oligonucleotide synthesis. It is usually bound to a molecule...

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Pyrimidine

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showed how pyrimidine nucleosides can be synthesized from small molecules and ribose, driven solely by wet-dry cycles. Purine nucleosides can be synthesized...

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Purine metabolism

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step to purine synthesis because PRPP is also used in pyrimidine synthesis and salvage pathways. The first committed step is the reaction of PRPP, glutamine...

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RNA world

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2018). "Glycosylation of a model proto-RNA nucleobase with non-ribose sugars: implications for the prebiotic synthesis of nucleosides". Organic & Biomolecular...

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Guanosine triphosphate

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Guanosine-5'-triphosphate (GTP) is a purine nucleoside triphosphate. It is one of the building blocks needed for the synthesis of RNA during the transcription process...

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Charlie Gard case

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different gene (TK2), which also impairs the synthesis of nucleosides in mitochondria causing a less severe form of MDDS.: 20  The hospital's ethics committee...

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Vidarabine

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against herpes simplex and varicella zoster viruses. In the 1950s two nucleosides were isolated from the Caribbean sponge Tethya crypta: spongothymidine...

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Nucleic acid metabolism

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Pyrimidine nucleosides include cytidine, uridine, and thymidine. The synthesis of any pyrimidine nucleotide begins with the formation of uridine. This...

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Xanthosine phosphorylase

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and the synthesis of nucleotides, making it a member of the purine nucleoside phosphorylase group. This protein can degrade all purine nucleosides (including...

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Acetonitrile

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used in oligonucleotide synthesis from nucleoside phosphoramidites. Industrially, it is used as a solvent for the manufacture of pharmaceuticals and photographic...

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Nucleotide salvage

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nucleosides that are formed during degradation of RNA and DNA. This is important in some organs because some tissues cannot undergo de novo synthesis...

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Boranophosphate

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phosphoramidite stage in the synthesis of nucleosides. The P-BH3 bond is sufficiently robust to survive deprotection methods to allow formation of the triphosphate...

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Nucleobase

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that form nucleosides, which, in turn, are components of nucleotides, with all of these monomers constituting the basic building blocks of nucleic acids...

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Pyrimidine metabolism

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organic synthesis. De Novo biosynthesis of a pyrimidine is catalyzed by three gene products CAD, DHODH and UMPS. The first three enzymes of the process...

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Salvage enzyme

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for the manufacture of DNA. They catalyze the phosphorylation of nucleosides to nucleoside - 5'-phosphates, that are further phosphorylated to triphosphates...

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