16667-60-0

Basic information

• Product Name: Uridine, 3'-benzoate
• CAS NO: 16667-60-0
• Molecular Formula: C16H16N2O7
• Molecular Weight: 348.312
• Mol File: 16667-60-0.mol

Chemical Properties

• CAS DataBase Reference: Uridine, 3'-benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 3'-benzoate(16667-60-0)
• EPA Substance Registry System: Uridine, 3'-benzoate(16667-60-0)

Safety Data

• Hazardous Substances Data: 16667-60-0(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 42822-78-6 2,3’-O-dibutylstannyleneuridine 
• 16667-59-7 2’,3’-methoxybenzylideneuridine 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 58-96-8 uridine 

Downstream Products

• 115142-19-3 4-nitrophenyl 2',5',-di-O-tetrahydropyranyluridine-3'-phosphate 
• 115142-06-8 uridine 3'-(p-nitrophenyl phosphate) 
• 96041-77-9 5'-O-(4,4'-dimethoxytrityl)-3'-O-benzoyluridine 

Relevant articles and documents

The Mechanism of Cleavage of RNA Phosphodiesters by a Gold Nanoparticle Nanozyme

The cleavage of uridine 3’-phosphodiesters bearing alcohols with pKa ranging from 7.14 to 14.5 catalyzed by AuNPs functionalized with 1,4,7-triazacyclononane-Zn(II) complexes has been studied to unravel the source of catalysis by these nanosystems (nanozymes). The results have been compared with those obtained with two Zn(II) dinuclear catalysts for which the mechanism is fairly understood. Binding to the Zn(II) ions by the substrate and the uracil of uridine was observed. The latter leads to inhibition of the process and formation of less productive binding complexes than in the absence of the nucleobase. The nanozyme operates with these substrates mostly via a nucleophilic mechanism with little stabilization of the pentacoordinated phosphorane and moderate assistance in leaving group departure. This is attributed to a decrease of binding strength of the substrate to the catalytic site in reaching the transition state due to an unfavorable binding mode with the uracil. The nanozyme favors substrates with better leaving groups than the less acidic ones.

Lanthanide catalyzed cyclization of uridine 3′-p-nitrophenyl phosphate

Steady state kinetics and 15N isotope effects have been used to study the cyclization reaction of uridine 3′-p-nitrophenyl phosphate. The cyclization reaction is catalyzed by transition metal ions and lanthanides, as are substitution reactions of many phosphate esters. Kinetic analysis reveals that the erbium-catalyzed cyclization reaction involves the concerted deprotonation of the 2′-OH group and departure of the leaving group. The transition state is very late, with a very large degree of bond cleavage to the leaving group, which could be due to a large degree of polarization of the P-O bonds by erbium.

A universal adapter for chemical synthesis of DNA or RNA on any single type of solid support

Use of a novel nucleotide adapter, 2'(3')-O-dimethoxytrityl-3'(2')-O-benzoyluridine-5'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) eliminates the need to have eight separate solid supports for synthesis of all possible oligoribo- and oligodeoxyribonucleotides.