173978-68-2

Usage

Uses

Used in Pharmaceutical Industry:
Cytidine, 2'-deoxy-N-(phenylacetyl)is used as a precursor in the synthesis of various pharmaceutical compounds for its unique structural properties that can be utilized in drug development.
Used in Biomedical Research:
This chemical is used as a research tool in biomedical research to study its potential applications and therapeutic properties, contributing to the advancement of medical knowledge and treatment options.
Used in Drug Development:
Cytidine, 2'-deoxy-N-(phenylacetyl)is employed in drug development for its potential therapeutic properties, with ongoing research aimed at understanding its full potential and how it can be applied to treat various conditions.

Upstream product

• 51432-42-9 4-Amino-1-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 
• 55628-82-5 1-(Phenylacetyl)imidazole 
• 102434-71-9 2'-deoxy-3',5'-di-O-1,1,3,3-(tetraisopropyldisiloxane-1,3-diyl)cytidine 
• 103-82-2 phenylacetic acid 
• 1555-80-2 phenylacetic anhydride 
• 951-77-9 2'-Deoxycytidine 
• 51432-39-4 N⁴,O^3'_,O5'-tris-trimethylsilanyl-2'-deoxy-cytidine 
• 103-80-0 phenylacetyl chloride 
• 30516-21-3 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-phenylethan-1-one 

Downstream Products

• 182688-59-1 Methyl-phosphonic acid mono-[(2R,3S,5R)-3-hydroxy-5-(2-oxo-4-phenylacetylamino-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester 
• 190192-16-6 5'-O-Dimethoxytrityl-4-N-phenylacetyl-2'-deoxycytidine 
• 190192-17-7 Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-oxo-4-phenylacetylamino-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester 
• 221351-11-7 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid γ-allyl ester-methoxyethyl ester 
• 221351-10-6 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-glutamic acid-γ-allyl ester methyl ester 
• 197727-37-0 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-valyl-L-phenylalanine-methoxyethoxyethyl ester 
• 197727-35-8 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-serine-L-glutamic acid γ-allyl ester-methoxyethoxyethyl ester 
• 197727-36-9 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-seryl-L-phenylalanine-methoxyethoxyethyl ester 
• 197727-30-3 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-serine 
• 197727-27-8 N-Allyloxycarbonyl-O-(3'-O-acetyl-6-N-phenylacetyl-2'-deoxycytidine-allyl-phosphato)-L-serine methyl ester 
• 203986-33-8 3'-O-Acetyl-5'-O-dimethoxytrityl-4-N-phenylacetyl-2'-deoxycytidine 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of nucleopeptides

Nucleoproteins, in which the hydroxy group of a serine, a threonine, or a tyrosine, is linked through a phosphodiester group to the 3′- or 5′-end of DNA or RNA, play decisive roles in important biological processes. They may even have a major part in the process of viral replication by nucleoprotein-primed elongation of the oligonucleotide strand. For the study of the biological phenomena, in which nucleoproteins are involved, nucleopeptides with the characteristic linkage between the peptide chain and the oligonucleotide of their parent nucleoproteins may serve as powerful tools. However, the synthesis of these compounds is complicated by their pronounced acid- and base-lability, as well as their multifunctionality. As a result, protecting groups, which can be removed under the mildest conditions, are required. For the construction of such peptide conjugates using a flexible building block strategy, a combination of enzyme-labile and chemical protecting groups was developed. The C-terminal blocking function can be removed selectively from fully protected nucleoamino acid methyl, 2-methoxyethyl (ME), and methoxyethoxyethyl (MEE) esters by saponification of the esters. After elongation of the peptide chain with amino acid or peptide methyl, ME, MEE, and choline esters, the C-terminal ester blocking group can again be removed easily. The methyl, ME, and MEE esters are cleaved off with lipase, and the choline ester group is selectively attacked by butyrylcholine esterase. The nucleoamino acids and peptides formed may be fully deprotected. To this end, the enzyme-labile N-phenylacetyl (PhAc) group, which was employed to mask the amino functions of the nucleobases, was removed. The O-acetate in the deoxyribose was saponified, and the allyl protecting groups present were cleaved by Pd0-mediated allyl transfer. By combination of these techniques, a nucleopeptide was produced, which represents the characteristic linkage region of the nucleoprotein of adenovions 2. The conditions, under which the enzymatic deprotections proceed, are so mild that no undesired side reaction is observed, that is no depurination or β elimination of the nucleosides occurs. In addition, the specificity of the biocatalysts ensures that the peptide bonds and the other protecting groups present are not attacked either.

An enzymatic protecting group strategy for the synthesis of nucleopeptides

Enzymatic protecting group techniques are used for the selective synthesis of acid- and base labile multifunctional nucleopeptides under mild conditions.

Chemoenzymatic synthesis of nucleopeptides

Acid- and base-labile multifunctional nucleopeptides have been selectively constructed under mild conditions by means of enzymatic protecting group techniques.

Nucleosides, nucleotides and oligonucleotides containing enzymatically cleavable protecting groups

Process for the production of oligonucleotides of formula II, in which the exocyclic amino groups of the bases adenine, guanine, cytosine, 7-deazaadenine and 7-deazaguanine carry N-phenylacetyl groups, are used for oligonucleotide synthesis, wherein in a first step a starting nucleotide is bound to a solid carrier, subsequently the desired oligonucleotide is synthesized by stepwise coupling with appropriately activated further monomeric nucleotide building blocks of the general formula I with the above-mentioned meanings, if desired, trivalent phosphorus is oxidized to pentavalent phosphorus during and after the synthesis, the oligonucleotide is cleaved from the carrier and the 5' protecting groups are cleaved off. The phenylacetyl functional groups that protect exocyclic NH2 groups of the bases can be cleaved off in a mild way with penicillin amidohydrolase (EC 3.5.1.11).

Chemoenzymic synthesis of P(α)-methyl deoxynucleoside triphosphates

5'-O-(methylphosphonyl)-N-(phenylacetyl)-2'-deoxycytidine, deoxyadenosine and deoxyguanosine were pyrophosphorylated and the resulting N-protected P(α)-methyl nucleoside triphosphates were deblocked by treatment with penicillin amidase at pH 7.8, 25°C to give P(α)-methyl nucleoside triphosphates.

A simple method for N-acylation of adenosine and cytidine nucleosides using carboxylic acids activated in-situ with carbonyldiimidazole

Carboxylic acids are activated with 1,1'-carbonyldiimidazole in acetonitrile to form N-acylimidazoles which are then treated with per-trimethylsilyl ethers of nucleosides adenosine or cytidine at ambient temperature to generate exclusively N-acylated-Aden