199593-09-4

Basic information

• Product Name: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• Synonyms: 2’-O-Methyl-rC(N-Ac)Phosphoramidite;5'-O-DMT-2'-O-Me-rC(N-Ac)-3'-CEDPA;N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite;2'-OMe-Ac-C Phosphoramidite;N4-Acetyl-5'-O-DMT-2'-O-methylcytidine 3'-CE phosphoramidite;DMT-2′O-Methyl-rC(ac) Phosphoramidite;2'-O-Methyl-N4-Acetyl-5'-O-DMT-Cytidine-3'-CE-Phosphoramidite;5'-DMT-2'-OMe-rC(N-Ac) Phosphoramidite
• CAS NO: 199593-09-4
• Molecular Formula: C₄₂H₅₂N₅O₉P
• Molecular Weight: 801.873
• EINECS: 2017-001-1
• Mol File: 199593-09-4.mol
• Article Data: 1

Chemical Properties

• Appearance: white to off-white/
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.18±0.20(Predicted)
• CAS DataBase Reference: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(199593-09-4)
• EPA Substance Registry System: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite(199593-09-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 199593-09-4(Hazardous Substances Data)

Usage

Description

N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite, also known as 2''-OMe-Ac-C Phosphoramidite, is a nucleotide derivative with a unique chemical structure. It is characterized by the presence of an N-acetyl group, a 4,4-dimethoxytrityl group, a 2'-O-methylcytidine moiety, and a 3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite group. N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite plays a crucial role in the field of molecular biology and biotechnology, particularly in the synthesis of specific types of oligonucleotides.

Uses

Used in Molecular Biology and Biotechnology:
N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is used as a key building block in the solid-phase synthesis of phosphorothioate oligonucleotides. These oligonucleotides are essential for various applications, including the development of novel therapeutics, the study of gene expression, and the investigation of molecular interactions.
Used in the Synthesis of Phosphorothioate Oligonucleotides:
In the field of molecular biology, N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is employed as a crucial component in the synthesis of phosphorothioate oligonucleotides. These modified nucleic acids exhibit increased stability and resistance to degradation, making them ideal for use in various research and therapeutic applications.
Used in In Situ Capping:
N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-methylcytidine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite is also utilized for in situ capping of phosphorothioate oligonucleotides. This process involves the use of sulfurization byproducts to cap the oligonucleotides, which helps to improve their overall stability and performance in various applications.

Upstream product

• 124482-92-4 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine 
• 199593-08-3 N-(1-((2R,3R,4R,5R)-5-((bis(4-Methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxy-3-methoxytetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)acetamide 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 85335-73-5 N₄-acetyl-3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)cytidine 
• 3768-18-1 N-acetylcytidine 
• 113886-71-8 N⁴-acetyl-2'-O-methyl cytidine 
• 199593-14-1 N-[2-Oxo-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1,2-dihydro-pyrimidin-4-yl]-acetamide 

Downstream Products

• 138906-72-6 5'-O-dimethoxytritil-2'-O-methylcytidine-3'-O-(2-cianoethyl-N,N-diisopropylphosphoramidite) 

Relevant articles and documents

Ultrafast cleavage and deprotection of oligonucleotides synthesis and use of C(Ac) derivatives

We have investigated the use of alkylamines as fast cleavage and deprotection reagents for the solid phase synthesis of oligonucleotides and found methylamine/ammonium hydroxide (or methylamine) as an efficient reagent. The transamination side product formed with the commonly used dC(b2) has been eliminated by the use of dC(Ac) phosphoramidite. This system has successfully been used in the synthesis of oligonucleotides and oligonucleoside phosphorothioates. DMT dC(Ac) hydrogen phosphonate and DMT ribo C(Ac)-2'-OMe phosphoramidite also have been prepared and used in the synthesis of oligonucleotides.