CAS 104086-76-2

2′,3′-Dideoxycytidine 5′-monophosphate

Description:

2′,3′-Dideoxycytidine 5′-monophosphate (ddCMP) is a nucleotide analog that plays a significant role in molecular biology and pharmacology, particularly in the study of antiviral agents. It is a derivative of cytidine, where the hydroxyl groups at the 2' and 3' positions of the ribose sugar are replaced with hydrogen atoms, rendering it a dideoxynucleotide. This modification impedes the ability of DNA polymerases to incorporate ddCMP into DNA strands, thus inhibiting viral replication. ddCMP is typically used in research settings to investigate mechanisms of nucleic acid synthesis and to develop antiviral therapies, especially against retroviruses like HIV. The compound is soluble in water and exhibits stability under physiological conditions, although it is sensitive to hydrolysis. Its structure includes a phosphate group attached to the 5' carbon of the ribose, which is crucial for its function as a nucleotide. Overall, ddCMP serves as a valuable tool in both basic and applied research in biochemistry and molecular biology.

Formula: C₉H₁₄N₃O₆P

InChI: InChI=1S/C9H14N3O6P/c10-7-3-4-12(9(13)11-7)8-2-1-6(18-8)5-17-19(14,15)16/h3-4,6,8H,1-2,5H2,(H2,10,11,13)(H2,14,15,16)/t6-,8+/m0/s1

InChI key: InChIKey=RAJMXAZJKUGYGW-POYBYMJQSA-N

SMILES: O=C1N([C@@H]2O[C@H](COP(=O)(O)O)CC2)C=CC(N)=N1

Synonyms:

• 2',3'-Dideoxy-5'-Cytidylicaci
• 2',3'-Dideoxycytidine monophosphate
• 2′,3′-Dideoxy-5′-cytidylic acid
• 2′,3′-Dideoxycytidine 5′-monophosphate
• 2′,3′-Dideoxycytidine monophosphate
• 5'-Cytidylic acid, 2',3'-dideoxy-
• 5′-Cytidylic acid, 2′,3′-dideoxy-
• Cytidine-5'-Monophosphate Monohydrate
• Zalcitabine monophosphate
• [(2S,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate

((2S,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate

CAS: 104086-76-2

Formula: C₉H₁₄N₃O₆P

Color and Shape: Solid

Molecular weight: 291.1977

Ref: IN-DA008R8N

2',3'-Dideoxycytidine 5'-monophosphate

CAS: 104086-76-2

Dideoxycytidine 5'-monophosphate (DDCMP) is a molecule that inhibits HIV infection by inhibiting the synthesis of DNA. It binds to the dna template strand, preventing the addition of new nucleotides and thus blocking the progression of HIV infection. DDCMP has been shown to be potent in vitro and in vivo in clinical studies. In cell culture, DDCMP has been shown to inhibit DNA duplexes, leading to a decrease in lymphocytic leukemia cells activated by T-cell receptor stimulation. Structural biology studies have revealed that DDCMP inhibits HIV-1 reverse transcriptase through binding at the M2 subunit of the enzyme's active site.

Formula: C₉H₁₄N₃O₆P

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 291.2 g/mol

Ref: 3D-ND170662