33422-70-7

Basic information

• Product Name: Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate
• Synonyms: [9-(tri-O-acetyl-β-D-ribofuranosyl)-9H-purin-6-yl]-carbamic acid ethyl ester;Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-ethoxycarbonylamino-purin-9-yl)-tetrahydro-furan-3-yl ester;O2',O3',O5'-triacetyl-N6-ethoxycarbonyl-adenosine;N6-(ethoxycarbonyl)-2',3',5'-tri-O-acetyladenosine
• CAS NO: 33422-70-7
• Molecular Formula: C19H23N5O9
• Molecular Weight: 465.42
• Mol File: 33422-70-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate(33422-70-7)
• EPA Substance Registry System: Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate(33422-70-7)

Safety Data

• Hazardous Substances Data: 33422-70-7(Hazardous Substances Data)

Usage

Description

Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate is a modified nucleoside derivative that plays a crucial role in various biological processes. It is an intermediate in the synthesis of N6-(N-Threonylcarbonyl)adenosine (T405560), an essential modified nucleoside found in tRNA responsible for ANN codons in all three domains of life. Additionally, it serves as a biological marker in neoplastic diseases, making it a significant compound in the field of biochemistry and molecular biology.

Uses

Used in Pharmaceutical Industry:
Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate is used as an intermediate in the synthesis of N6-(N-Threonylcarbonyl)adenosine (T405560) for its role in the formation of tRNA and its involvement in protein synthesis. This application is crucial for understanding the molecular mechanisms underlying various biological processes and the development of novel therapeutic strategies.
Used in Diagnostics:
Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate is used as a biological marker in the detection and monitoring of neoplastic diseases. Its presence in tRNA and its association with ANN codons make it a valuable tool for researchers and clinicians in identifying and characterizing cancerous cells, thereby aiding in the development of targeted therapies and personalized treatment plans.
Used in Research and Development:
Adenosine, N-(ethoxycarbonyl)-, 2',3',5'-triacetate is used as a key compound in research and development efforts aimed at understanding the molecular basis of various diseases and the development of novel therapeutic agents. Its role in tRNA synthesis and its potential as a biological marker make it an important target for further investigation and exploration in the fields of molecular biology, genetics, and pharmacology.

Upstream product

• 96394-56-8 N⁶-(1-ethoxy-2-chloroethylidene)-2',3',5'-tri-O-acetyladenosine 
• 58-61-7 adenosine 
• 541-41-3 chloroformic acid ethyl ester 
• 7387-57-7 triacetyladenosine 
• 96394-53-5 8-ethoxy-3-(2',3',5'-tri-O-acetylribofuranosyl)imidazo<2,1-i>purine 

Downstream Products

• 24719-82-2 N⁶-threonylcarbamoyladenosine 
• 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 
• 292054-00-3 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 
• 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 

Relevant articles and documents

Stability studies on the newly discovered cyclic form of tRNA N 6-threonylcarbamoyladenosine (ct6A)

A cyclic form of N6-threonylcarbamoyladenosine bearing an oxazolone moiety (ct6A) was discovered very recently at the position 37 in several tRNA sequences. Our study on the synthesized 5′,3′, 2′-O-acetylated derivative of ct6A confirmed high stability of the modified nucleoside under physiological conditions (PBS buffer, pH 7.4) and revealed remarkable stability of the oxazolone ring in acidic (100 mM HCl, pH 1) and basic (0.1 mM NaOH, pH 10) conditions. This feature may allow for the post-synthetic conversion of t6A into ct6A in assembled oligoribonucleotides.

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.