292054-00-3

Basic information

• Product Name: 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester
• CAS NO: 292054-00-3
• Molecular Weight: 1043.49
• Mol File: 292054-00-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester(292054-00-3)
• EPA Substance Registry System: 5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester(292054-00-3)

Safety Data

• Hazardous Substances Data: 292054-00-3(Hazardous Substances Data)

Upstream product

• 58-61-7 adenosine 
• 7387-57-7 triacetyladenosine 
• 33422-70-7 ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 292053-99-7 5'-O-(4,4'-dimethoxytrityl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 
• 56893-27-7 2-(3-(9-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)ureido)-3-hydroxybutanoic acid 
• 292053-97-5 (2,3,5-tri-O-acetyl-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl])-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 
• 292053-96-4 C₂₇H₄₀N₆SiO₁₁SiC₆H₁₄ 
• 292053-91-9 N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 
• 292053-90-8 (2,3,5-tri-O-acetyl-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl])-O-tert-butyldimethylsilyl-L-threonine 

Downstream Products

• 292053-98-6 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester 

Relevant articles and documents

Synthesis and characterization of the native anticodon domain of E. coli tRNA(Lys): Simultaneous incorporation of modified nucleosides mnm5s2U, t6A, and pseudouridine using phosphoramidite chemistry

The anticodon domain of E. coli tRNA(Lys) contains the hypermodified nucleosides mnm5s2U and t6A at positions 34 and 37, respectively, along with a more common ψ at position 39. The combination of these three nucleotides represents one of the most extensively modified RNA domains in nature. 2-Cyanoethyl diisopropylphosphoramidites of the hypermodified nucleosides mnm5s2U and t6A were each synthesized with protecting groups suitable for automated RNA oligonucleotide synthesis. The 17 nucleotide anticodon stem-loop of E. coli tRNA(Lys) was then assembled from these synthons using phosphoramidite coupling chemistry. Coupling efficiencies for the two hypermodified nucleosides and for pseudouridine phosphoramidite were all greater than 98%. A mild deprotection scheme was developed to accommodate the highly functionalized RNA. High coupling yields, mild deprotection, and efficient HPLC purification allowed us to obtain 1.8 mg of purified RNA from a 1 μmol scale RNA synthesis. Our efficient synthetic protocol will allow for biophysical investigation of this rather unique tRNA species wherein nucleoside modification has been shown to play a role in codon-anticodon recognition, tRNA aminoacyl synthetase recognition, and programmed ribosomal frameshifting. The human analogue, tRNA(Lys,3), is the specific tRNA primer for HIV-1 reverse transcriptase and has a similar modification pattern.