51549-31-6

Upstream product

• 141479-79-0 3'-O-TBDMS-5'-O-TBDPS-2'-deoxyadenosine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 958-09-8 2'-deoxy-D-adenosine 
• 1233510-51-4 3'-O-(tert-butyldimethylsilyl)-5'-O-(4,4'-dimethoxytrityl)-6-N-[(dimethylamino)methylene]-2'-deoxyadenosine 
• 17331-20-3 5'-O-(4,4'-Dimethoxytrityl)-N⁶-dimethylformamidine-2'-deoxyadenosine 
• 17331-22-5 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-2'-deoxyadenosine 
• 898253-80-0 8-bromo-O₃'-(tert-butyldimethylsilyl)-2'-deoxyadenosine 
• 51549-32-7 3',5'-bis-O-[(tert-butyl)dimethylsilyl]-2'-deoxyadenosine 
• 89947-86-4 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 

Downstream Products

• 1065269-49-9 (E)-3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylprop-2-en-1-one 
• 1233510-66-1 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 
• 1082489-87-9 6-N-[(dimethylamino)methylene]-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite) 
• 1233510-54-7 3'-O-(tert-butyldimethylsilyl)-5'-O-[(4-methoxytrityl)sulfenyl]-2'-deoxyadenosine 
• 94219-36-0 o-chlorophenyl 5'-O-p-methoxytrityl-2'-deoxyguanylyl(3'-5')-3'-O-t-butyldimethylsilyl-2'-deoxyadenosine 
• 94189-91-0 o-chlorophenyl 5'-O-p-methoxytrityl-2'-deoxyadenylyl(3'->5')-3'-O-tert-butyldimethylsilyl-2'-deoxyadenosine 
• 94189-96-5 Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 
• 94189-93-2 o-chlorophenyl 5'-O-t-butyldimethylsilyl-thymidylyl(3'-5')-3'-O-t-butyldimethylsilyl-2'-deoxyadenosine 
• 94189-94-3 Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester 2-chloro-phenyl ester 

Relevant academic research and scientific papers

MODIFIED NUCLEOTIDES FOR SYNTHESIS OF NUCLEIC ACIDS, A KIT CONTAINING SUCH NUCLEOTIDES AND THEIR USE FOR THE PRODUCTION OF SYNTHETIC NUCLEIC ACID SEQUENCES OR GENES

A modified nucleotide, intended for the synthesis of long chain nucleic acids by enzymatic processes, comprising a “natural” nitrogenous base or a natural nitrogenous base analogue, a ribose or deoxyribose carbohydrate, and at least one phosphate group, characterized in that said nucleotide comprises at least one R group, termed the modifier group, carried by said nitrogenous base or analogue and/or by the oxygen in position 3′ of the ribose or deoxyribose molecule, making it possible to block the polymerization of said nucleotide and/or to allow the interaction of said nucleotide with another molecule, such as a protein, during the nucleic acid synthesis, R comprising at least one functional terminal group.

Synthesis of disaccharide nucleosides by the O-glycosylation of natural nucleosides with thioglycoside donors

Disaccharide nucleosides constitute an important group of naturally-occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O-glycosylation of nucleoside acceptors, such as adenosine, guanosine, thy

Synthesis of oligodeoxynucleotides using the oxidatively cleavable 4-methoxytritylthio (MMTrS) group for protection of the 5'-hydroxyl group

We examined the synthesis of oligodeoxynucleotides containing all four nucleobases using the 4-methoxytritylthio (MMTrS) group for protection of the 5'-hydroxyl group. The MMTrS group could be introduced into 3'-O-TBDMS- deoxycytidine, -deoxyadenosine and -deoxyguanosine with the appropriate base protecting groups using strong bases such as n-butyl lithium and lithium hexamethyldisilazide. Because the MMTrS group could be removed by oxidation with an aqueous I2 solution, the oxidation of internucleotidic phosphite intermediates could be performed simultaneously. Thus, the nucleotide chain could be extended in a three-step protocol that comprised coupling, capping and oxidation/deprotection. Oligodeoxynucleotides with 10 and 20 mixed-base sequences could be synthesized using this protocol.

Antibacterial Agents

The invention provides compounds of formula (I) and salts thereof: R1-L-R2—B wherein R1, L, R2, and B have any of the values defined herein, as well as compositions comprising such compounds, and therapeutic methods comprising the administration of such compounds or salts. The compounds block siderophore production in bacteria and are useful as antibacterial agents.

Synthesis and evaluation of 5′-modified 2′-deoxyadenosine analogues as anti-hepatitis C virus agents

In order to study the effect of 5′-modification of 2′-deoxynucleoside on its anti-HCV activity, several analogues were synthesized and evaluated. Among the analogues, a 5′-deoxy-5′-phenacylated analogue exhibited a good anti-HCV activity with an EC50 of 15.1 μM. This compound is expected to operate via a type of mechanism that does not involve a generally known 5′-O-triphosphorylation process.

C5′-adenosinyl radical cyclization. A stereochemical investigation

A variety of substituted 2′-deoxyadenosin-5′-yl radicals 3 were generated under different reaction conditions. Radicals 3 underwent intramolecular cyclization onto the C8-N7 double bond of the adenine moiety leading to aminyl radicals (5′S,8R)-4 and (5′R,8R)-4 and, eventually, to the corresponding cyclonucleosides 5 and 6. The effect of the solvent, the nature of the substituents, and the generation method of radicals 3 on the stereoselectivity of the C5′-radical cyclization have been considered. The observed increase of the (5′S)/(5′R) ratio by increasing the bulkiness of the R1 group is explained in terms of steric repulsion between R1 and the purine moiety which favors the C5′-endo conformation, whereas the effect of the water solvent in promoting the (5′R)-stereoselective cyclization is ascribed to intermolecular hydrogen bonding stabilizing the C5′-exo confomation.

Antitubercular nucleosides that inhibit siderophore biosynthesis: SAR of the glycosyl domain

Tuberculosis is the leading cause of infectious disease mortality in the world by a bacterial pathogen. We previously demonstrated that a bisubstrate inhibitor of the adenylation enzyme MbtA, which is responsible for the second step of mycobactin biosynth

Deoxyribosyl analogues of methionyl and isoleucyl sulfamate adenylates as inhibitors of methionyl-tRNA and isoleucyl-tRNA synthetases

2′-Deoxy, 3′-deoxy, and 2′,3′-dideoxyribosyl surrogates of isoleucyl and methionyl sulfamate adenylates have been investigated to identify the pharmacophoric importance of the ribose group for the inhibition of Escherichia coli methionyl-tRNA (MRS) and isoleucyl-tRNA (IRS) synthetases. Molecular modeling of 2′,3′-dideoxyribosyl Met-NHSO2-AMP (9) with the crystal structure of E. coli MRS revealed that the lack of the two hydroxyl groups on ribose was compensated by the formation of an extra hydrogen bond between the ring oxygen and His24, resulting in a small activity reduction.

1,1,1,3,3,3-Hexafluoro-2-propanol for the Removal of the 4,4'-Dimethoxytrityl Protecting Group from the 5'-Hydroxyl of Acid-Sensitive Nucleosides and Nucleotides

1,1,1,3,3,3-Hexafluoro-2-propanol is introduced as a suitable reagent and solvent for the detritylation of 5'-O-(4,4'-dimethoxytrityl)-nucleosides and -deoxy- nucleosides, especially those that are susceptible to N-glycosyl cleavage under more strongly acidic conditions.