CAS 51034-68-5

2′-Azido-2′-deoxycytidine

Description:

2′-Azido-2′-deoxycytidine, commonly referred to as AZT or zidovudine, is a nucleoside analog with significant relevance in antiviral therapy, particularly for the treatment of HIV/AIDS. It is characterized by the presence of an azido group at the 2′ position of the deoxyribose sugar, which distinguishes it from the natural nucleoside cytidine. This modification impedes the reverse transcriptase enzyme, thereby inhibiting viral replication. AZT is typically administered in its phosphate form, which is active in cellular metabolism. The compound exhibits a relatively low toxicity profile in human cells, although it can lead to side effects such as bone marrow suppression and gastrointestinal disturbances. Its mechanism of action involves incorporation into viral DNA, leading to chain termination during DNA synthesis. AZT is often used in combination with other antiretroviral agents to enhance therapeutic efficacy and reduce the risk of resistance development. The compound is soluble in water and has a moderate stability profile under physiological conditions, making it suitable for clinical use.

Formula: C₉H₁₂N₆O₄

InChI: InChI=1S/C9H12N6O4/c10-5-1-2-15(9(18)12-5)8-6(13-14-11)7(17)4(3-16)19-8/h1-2,4,6-8,16-17H,3H2,(H2,10,12,18)/t4-,6-,7-,8-/m1/s1

InChI key: InChIKey=FEOYKPQEERVCAV-XVFCMESISA-N

SMILES: N(=[N+]=[N-])[C@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C(=O)N=C(N)C=C2

Synonyms:

• 2'-Azidocytidine
• 2′-Deoxy-2′-azidocytidine
• 4-amino-1-(2-azido-2-deoxypentofuranosyl)pyrimidin-2(1H)-one
• Cytidine, 2'-azido-2'-deoxy-
• NSC 678532
• 2′-Azido-2′-deoxycytidine
• 2'-Azido-2'-deoxycytidine

2'-Azido-2'-deoxycytidine

CAS: 51034-68-5

2'-Azido-2'-deoxycytidine

Purity: ≥98%

Molecular weight: 268.23g/mol

Ref: 54-BUP21128

2''-Azido-2''-deoxycytidine

CAS: 51034-68-5

Formula: C₉H₁₂N₆O₄

Purity: (HPLC) ≥ 95.0%

Color and Shape: White to light yellow powder

Molecular weight: 268.2

Ref: 7W-GN2452

2'-Azido-2'-deoxycytidine

CAS: 51034-68-5

2'-Azido-2'-deoxycytidine is a nucleoside analogue and azido-modified cytidine that can undergo click chemistry reactions with alkyne, DBCO, or BCN groups.

Formula: C₉H₁₂N₆O₄

Purity: 98.47%

Color and Shape: Solid

Molecular weight: 268.23

Ref: TM-TNU0230

2'-Azido-2'-deoxycytidine

CAS: 51034-68-5

2'-Azido-2'-deoxycytidine is a nucleoside analog derived from cytidine, in which the 2'-hydroxyl group of the ribose is replaced by an azido group (–N₃), while the cytosine base and remaining sugar structure are preserved. This substitution imparts the molecule with bioorthogonal reactivity, enabling its use in chemical biology applications such as nucleic acid labeling via azide-alkyne "click" chemistry. The azido group also sterically and electronically alters sugar conformation and enzymatic recognition, which can affect its incorporation into DNA or RNA by polymerases. Consequently, 2'-azido-2'-deoxycytidine is a useful research tool.

Formula: C₉H₁₂N₆O₄

Purity: Min. 95 Area-%

Color and Shape: Slightly Yellow Powder

Molecular weight: 268.2 g/mol

Ref: 3D-NA05412

2'-Azido-2'-deoxycytidine

Controlled Product

CAS: 51034-68-5

Formula: C₉H₁₂N₆O₄

Color and Shape: Neat

Molecular weight: 268.229

Ref: TR-A884580