155933-78-1

Basic information

• Product Name: C₇₃H₇₈N₇O₁₀PSi₂
• Synonyms: C₇₃H₇₈N₇O₁₀PSi₂
• CAS NO: 155933-78-1
• Molecular Weight: 1300.61
• Mol File: 155933-78-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₇₃H₇₈N₇O₁₀PSi₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₇₃H₇₈N₇O₁₀PSi₂(155933-78-1)
• EPA Substance Registry System: C₇₃H₇₈N₇O₁₀PSi₂(155933-78-1)

Safety Data

• Hazardous Substances Data: 155933-78-1(Hazardous Substances Data)

Upstream product

• 104992-55-4 N⁶-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) 
• 155933-77-0 <8-<(tert-butyldiphenylsilyl)oxy>quinolyl>methanol 

Relevant articles and documents

One- and two-metal ion catalysis of the hydrolysis of adenosine 3'-alkyl phosphate esters. Models for one- and two-metal ion catalysis of RNA hydrolysis

Adenosine 3'-O(PO2-)OCH2R phosphate esters have been synthesized with R = 8-hydroxyquinol-2-yl (1a) and 8-(hydroxyquinolyl)-2-methylene (1b). The adenosine 3'-O(PO2-)OCH2R structure has the essential features of an RNA dinucleotide. Equilibrium binding studies with metal ions Mg2+, Zn2+, Cu2+, and La3+ have been carried out with 1a, 1b, HOCH2R (7a and 7b), and 8-hydroxyquinoline (8), and equilibrium constants (K(as)) have been determined for the formation of 1:1 (L)M(n+) complexes. The hydrolysis of 1a and 1b as well as (1a)M(n+) and (1b)M(n+) species are first order in HO-. The rate enhancement for hydrolysis of 1a by complexation with metal ions is as follows: ~105 with Zn2+, ~103 with Mg2+, ~105 with Cu2+, and ~109 with La3+. Molecular modeling indicates that metal ions ligated to the 8-hydroxyquinoline moiety in the complexes (1a)M(n+) and (1b)M(n+) catalyze 1a and 1b hydrolysis by interacting as Lewis acid catalysts with the negatively charged oxygen atom of the phosphate group. In the instance of La3+ complexes, the ligated metal ion is within an interactive distance with both the negative phosphate oxygen and the leaving oxygen. This bimodal assistance by La3+ to the displacement reaction at phosphorus by the 2'-hydroxyl anion results in remarkable rate accelerations for the hydrolysis of (1a)La3+ and (1b)La3+ complexes. The complexes (1a)M(n+) and (1b)M(n+) are themselves hydrolyzed by metal ion catalysis in a reaction that is first order in HO-, an observation consistent with a transition state composition of [(1a,b)M(n+)][M(n+)][HO-]. We assume the kinetic equivalent [(1a,b)M(n+)][M(n+)OH] to represent the reacting species. In this catalysis the M(n+)OH is proposed to play the role of general base to deprotonate the 2'-OH while the metal in the complexes (1a,b)M(n+) is coordinated to a negative oxygen of the -(PO2-)- moiety. This double metal ion catalysis mimics a mechanism proposed for the ribozyme self-cleavage of RNA.