21052-18-6

Usage

Chemical Properties

White Foam

Uses

Protected 2-Thiouridine.

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 141-90-2 2-thiouracil 
• 22596-07-2 2',3',5'-tri-O-benzoyl-2,4-dithiouridine 
• 32865-74-0 4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 67525-66-0 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 

Downstream Products

• 155006-16-9 2-(acetonyl)thio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyrimidinone 
• 155006-17-0 2-(2-oxobutyl)thio-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyrimidinone 
• 52523-26-9 1-(2′,3′,5′-tri-O-benzoyl-β-D-ribofuranosyl)-4-pyrimidone 
• 1280117-35-2 2-ethylthio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)pyrimidine-4-one 
• 1280116-91-7 2-benzylthio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)pyrimidine-4-one 
• 1280116-90-6 2-propylthio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)pyrimidine-4-one 
• 1280116-92-8 2-phenylethylthio-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)pyrimidine-4-one 
• 3878-45-3 triphenylphosphine sulfide 
• 35763-29-2 2-thio UTP 
• 29123-25-9 2-Thio-uridin-5'-phosphat 
• 1748-04-5 tribenzoyl uridine 

Relevant academic research and scientific papers

Synthesis, base pairing and structure studies of geranylated RNA

Natural RNAs utilize extensive chemical modifications to diversify their structures and functions. 2-Thiouridine geranylation is a special hydrophobic tRNA modification that has been discovered very recently in several bacteria, such as Escherichia coli, Enterobacter aerogenes, Pseudomonas aeruginosa and Salmonella Typhimurium. The geranylated residues are located in the first anticodon position of tRNAs specific for lysine, glutamine and glutamic acid. This big hydrophobic terpene functional group affects the codon recognition patterns and reduces frameshifting errors during translation. We aimed to systematically study the structure, function and biosynthesis mechanism of this geranylation pathway, as well as answer the question of why nature uses such a hydrophobic modification in hydrophilic RNA systems. Recently, we have synthesized the deoxy-analog of S-geranyluridine and showed the geranylated T-G pair is much stronger than the geranylated T-A pair and other mismatched pairs in the B-form DNA duplex context, which is consistent with the observation that the geranylated tRNAGluUUC recognizes GAG more efficiently than GAA. In this manuscript we report the synthesis and base pairing specificity studies of geranylated RNA oligos. We also report extensive molecular simulation studies to explore the structural features of the geranyl group in the context of A-form RNA and its effect on codon-anticodon interaction during ribosome binding.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

Structural modifications of UMP, UDP, and UTP leading to subtype-selective agonists for P2Y2, P2Y4, and P2Y6 receptors

A large series of derivatives and analogues of the uracil nucleotides UMP, UDP, and UTP with modifications in various positions of the uracil moiety and/or the phosphate groups were synthesized and evaluated at human P2Y2, P2Y4, and P2Y6 receptors. 2-(Ar)alkylthio substitution of UMP and UDP was best tolerated by the P2Y2 receptor. 2-Phenethylthio-UMP (13e) showed an EC50 value of 1.3 μM at P2Y2 and >70-fold selectivity versus P2Y4 and P2Y 6 receptors. Substitution of the 2-keto group in UMP by NH (13g, iso-CMP) resulted in the first potent and selective P2Y4 agonist (EC50 4.98 μM, >20-fold selective vs P2Y2 and P2Y6). In contrast, replacement of the 2-keto function in UDP by NH yielded a potent P2Y2 agonist (12g, iso-CDP, EC50 = 0.604 μM, >100-fold selective). In an attempt to obtain metabolically stable UTP analogues, β,γ-dichloro- and β,γ-difluoro-methylene-UTP derivatives were synthesized. The triphosphate modifications were much better tolerated by P2Y2, and in some cases also by P2Y6, than by P2Y4 receptors. 4-Thio-β,γ-difluoromethylene-UTP (14g) was a potent P2Y2 agonist with an EC50 value of 0.134 μM and >50-fold selectivity. N3-Phenacyl-β,γ-dichloromethylene- UTP (14b) proved to be a potent P2Y6 receptor agonist (EC 50 0.142 μM) with high selectivity versus P2Y4 (50-fold) and moderate selectivity versus P2Y2 receptors (6-fold).

Synthesis and structure-activity relationships of uracil nucleotide derivatives and analogues as agonists at human P2Y2, P2Y4, and P2Y6 receptors

A series of UTP, UDP, and UMP derivatives and analogues were synthesized and evaluated at the human pyrimidinergic P2Y receptor subtypes P2Y2, P2Y4, and P2Y6 stably expressed in 1321N1 astrocytoma cells. Substituents at N3

Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane

A general and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings are the domain of desulfurization or formation of disulfides.

Synthesis of novel C-2 substituted pyrimidine nucleoside analogs

A series of 2-(2-oxoalkylidene)-4(1H)-pyrimidinone nucleoside analogs were synthesized by the addition of the lithium enolates of methylketones to 2,5'- and 2,2'-anhydrouridines and to 2,5'-anhydrothymidines. Alternatively, 2- thiouridine was alkylated with bromomethyl ketones to yield 2-(2- oxoalkyl)thio-4(1H)-pyrimidinone ribofuranosides in good yields. These intermediates were subsequently transformed into the title compounds via an Eschenmoser sulfur extrusion reaction. The 2-(2-oxoalkylidene)-4-(1H)- pyrimidinone nucleoside analogs exhibit enol proton signals in their 1H nmr spectra indicative of hydrogen bonding between N-3 and keto oxygen. These structures offer functional groups with potential for Watson-Crick hydrogen bonding.

Nucleoside Syntheses, XXV. A New Simplified Nucleoside Synthesis

The several steps of the Friedel-Crafts catalyzed silyl-Hilbert-Johnson nucleoside synthesis - silylation of the heterocyclic base, silylation of the perfluorosulfonic acids or its salts (if SnCl4 is not used as catalyst) and finally the nucleoside synthesis itself - can be combined to a simple one-step/one-pot reaction which generally affords nucleosides in high yields.

Process for the preparation of nucleosides

In a process for preparing a nucleoside by silylating the corresponding nucleoside base and reacting the silylated base with a 1-O-acyl, 1-O-alkyl, or 1-halogen derivative of a blocked monosaccharide or oligosaccharide in the presence of a catalyst, an improvement comprises silylating the base and reacting the sugar derivative in a single step.