263709-06-4

Basic information

• Product Name: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate
• Synonyms: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate
• CAS NO: 263709-06-4
• Molecular Weight: 801.883
• Mol File: 263709-06-4.mol

Chemical Properties

• CAS DataBase Reference: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate(263709-06-4)
• EPA Substance Registry System: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate(263709-06-4)

Safety Data

• Hazardous Substances Data: 263709-06-4(Hazardous Substances Data)

Upstream product

• 64898-58-4 2',3',5'-tri-O-acetyl-N⁶-(phenoxycarbonyl)adenosine 
• 263709-00-8 O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 263709-04-2 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-isocyanato-purin-9-yl)-tetrahydro-furan-3-yl ester 

Downstream Products

• 263709-12-2 2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine 
• 263709-10-0 N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine 
• 263709-08-6 N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 

Relevant articles and documents

Synthesis of the anticodon hairpin (t)RNA(f)(Met) containing N-{[9-(β- D-ribofuranosyl)-9H-purin-6-yl]carbamoyl}-l-threonine (= N6-{{[(1S,2R)-1- carboxy-2-hydroxypropyl]amino}carbonyl}adenosine, t6A)

As part of our studies on the structure of yeast 1RNA(f)(Met), we investigated the incorporation of N-{[9-(β-D-ribofuranosyl)-9H-purin-6- yl]carbamoyl}-L-threonine (t6A) in the loop of a RNA 17-mer hairpin. The carboxylic function of the L-threonine moiety of t6A was protected with a 2- (4-nitrophenyl)ethyl group, and a (tert-butyl)dimethylsilyl group was used for the protection of its secondary OH group. The 2'-OH function of the standard ribonucleotide building blocks was protected with a [(triisopropylsilyl)oxy]methyl group. Removal of the base-labile protecting groups of the final RNA with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and then with MeNH2 was done under carefully controlled conditions to prevent hydrolysis of the carbamate function, leading to loss of the L-threonine moiety.

Chemical synthesis of an RNA sequence containing 2-thiocytidine (s 2C): The DY647 labelled anticodon stem and loop sequence of Staphylococcus aureus tRNAArg (s2C32, mnm 5U34, t6A

Incorporation of 2-thiocytidine (s2C) into a DY647 labelled 17-mer RNA sequence corresponding to the anticodon stem loop of Staphylococcus aureus tRNAArg has been achieved by phosphoramidite chemistry. Key to the success was the use