114748-58-2

Basic information

• Product Name: 5-TFA-ap-2',3'-Dideoxycytidine
• Synonyms: 5-TFA-ap-2',3'-Dideoxycytidine;2',3'-Dideoxy-5-[3-[(trifluoroacetyl)amino]-1-propyn-1-yl]-cytidine
• CAS NO: 114748-58-2
• Molecular Formula: C14H15F3N4O4
• Molecular Weight: 360.2885096
• Mol File: 114748-58-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-TFA-ap-2',3'-Dideoxycytidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-TFA-ap-2',3'-Dideoxycytidine(114748-58-2)
• EPA Substance Registry System: 5-TFA-ap-2',3'-Dideoxycytidine(114748-58-2)

Safety Data

• Hazardous Substances Data: 114748-58-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-TFA-ap-2',3'-Dideoxycytidine is used as a potential antiviral agent for combating viral infections, particularly against Human Immunodeficiency Virus (HIV) and hepatitis B virus. Its unique structure and mechanism of action make it a promising candidate in the development of new antiviral drugs that offer improved efficacy and reduced toxicity compared to existing treatments.
Used in Antiviral Drug Development:
5-TFA-ap-2',3'-Dideoxycytidine serves as a key component in the research and development of novel antiviral medications. Its ability to terminate viral DNA synthesis positions it as a valuable asset in creating drugs that can effectively manage and treat viral diseases while minimizing side effects and toxicity concerns.

Upstream product

• 14719-21-2 trifluoroacetyl-propargyl amine 
• 114748-57-1 1-((S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-5-iodo-3,4-dihydro-1H-pyrimidin-2-one 
• 114748-57-1 5-iodo-2',3'-dideoxycytidine 

Relevant articles and documents

Palladium-Catalyzed Synthesis of Alkynylamino Nucleosides. A Universal Linker for Nucleic Acid

A method for attaching alkynylamino "linkers" to nucleosides and nucleotides is described.Protected or unprotected alkynylamines are coupled to iodonucleosides in dimethylformamide using a 1:2 mol ratio of tetrakis(triphenylphosphine)palladium(0) and copper(I) iodide, a catalyst system superior to the standard system using palladium(II) species.The resulting alkynylamino nucleosides are useful for enzymatic or chemical labeling of all four bases of DNA.

Alkynylamino-nucleotides

Alkynylamino-nucleotides and labeled alkynylaminonucleotides useful, for example, as chain terminating substrates for DNA sequencing are provided along with several key intermediates and processes for their preparation. For some applications, longer, hydrophilic linkers are provided.

Method of gene mapping

The method described characterizes each DNA segment to be mapped by cleaving it to produce DNA fragments which are then end labeled with a reporter(s) specific to the end nucleotides of each fragment. The labeled fragments are again cleaved to produce short fragments which are separated according to size. The short fragments are analyzed as to report identify and size which is indicative of the character of each fragment. By derivatizing the cleaved ends of the primary cleaved fragments, the labeling may be delayed until the second cleavage. Prior to the labeling the derivatized fragments, all underivatized fragments are removed, the derivatized fragments being immobilized.

Alkynylamino-nucleotides

Alkynylamino-nucleotides and labeled alkynylamino-nucleotides useful, for example, as chain terminating substrates for DNA sequencing are provided along with several key intermediates and processes for their preparation.

Solvent, not palladium oxidation state, is the primary determinant for successful coupling of terminal alkynes with iodo-nucleosides

Coupling of iodo-nucleosides with terminal alkynes such as 3-(acylamino)propynes, whose initial products readily undergo secondary cyclization reactions, can be effected smoothly by the standard catalysis with (Ph3P)2PdCl2