15648-73-4

Basic information

• Product Name: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-{[{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate (non-preferred name)
• CAS NO: 15648-73-4
• Molecular Formula: C₁₉H₂₆N₈O₁₄P₂
• Molecular Weight: 652.4025
• Mol File: 15648-73-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 1082.2°C at 760 mmHg
• Flash Point: 608.3°C
• Density: 2.34g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.903
• CAS DataBase Reference: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-{[{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-{[{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate (non-preferred name)(15648-73-4)
• EPA Substance Registry System: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-{[{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}-4-hydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate (non-preferred name)(15648-73-4)

Safety Data

• Hazardous Substances Data: 15648-73-4(Hazardous Substances Data)

Upstream product

• 88867-00-9 methyl (N⁴-benzoyl-2'-O-t-butyldimethylsilyl)cytidylyl (3'-> 5') (N⁶,O^2',O^3'-tribenzoyl)adenosine 
• 90907-24-7 2'-O-t-butyldimethylsilylcytidylyl (3'-> 5') adenosine 5'-monophosphate 

Downstream Products

• 88854-01-7 N⁴-(N-acetyl-D,L-phenylalanyl) cytidylyl (3'->5') adenosine 5'-phosphate 
• 2922-94-3 cytidine 3',5'-bis(monophosphate) 
• 58-61-7 adenosine 

Relevant articles and documents

Facile synthesis of N -acyl-aminoacyl-pCpA for preparation of mischarged fully ribo tRNA

Chemical synthesis of N-acyl-aminoacyl-pdCpA and its ligation to tRNAminus CA is widely used for the preparation of unnatural aminoacyl-tRNA substrates for ribosomal translation. However, the presence of the unnatural deoxyribose can decrease incorporation yield in translation and there is no straightforward method for chemical synthesis of the natural ribo version. Here, we show that pCpA is surprisingly stable to treatment with strong organic bases provided that anhydrous conditions are used. This allowed development of a facile method for chemical aminoacylation of pCpA. Preparative synthesis of pCpA was also simplified by using t-butyl-dithiomethyl protecting group methodology, and a more reliable pCpA postpurification treatment method was developed. Such aminoacyl-pCpA analogues ligated to tRNAminus CA transcripts are highly active in a purified translation system, demonstrating utility of our synthetic method.