CAS 14486-22-7

2',3'-Anhydroadenosine

Description:

2',3'-Anhydroadenosine is a nucleoside analog derived from adenosine, characterized by the absence of the hydroxyl group at the 2' and 3' positions of the ribose sugar. This structural modification imparts unique biochemical properties, making it an important compound in various biochemical and pharmacological studies. The compound is known for its role in cellular signaling and metabolism, particularly in the context of purine metabolism. It can influence cellular processes such as apoptosis and has been investigated for its potential therapeutic applications, including antiviral and anticancer activities. The compound is typically soluble in polar solvents, and its stability can be affected by environmental conditions such as pH and temperature. Additionally, 2',3'-Anhydroadenosine can serve as a substrate for specific enzymes, which can further elucidate its biological functions. Overall, its unique structural features and biological relevance make it a significant subject of research in the fields of biochemistry and medicinal chemistry.

Formula: C₁₀H₁₂N₂O₅

InChI: InChI=1/C10H12N2O5/c1-4-2-12(10(15)11-8(4)14)9-7-6(17-7)5(3-13)16-9/h2,5-7,9,13H,3H2,1H3,(H,11,14,15)/t5-,6?,7?,9-/m1/s1

SMILES: Cc1cn([C@H]2C3C([C@@H](CO)O2)O3)c(=O)nc1O

Synonyms:

• 1-[(1R,4R,5R)-4-(hydroxymethyl)-3,6-dioxabicyclo[3.1.0]hex-2-yl]-5-met hyl-pyrimidine-2,4-dione
• 1-(2,3-Anhydro-beta-D-lyxofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
• 2',3'-Anhydro-5-Methyluridine
• 1-(2,3-anhydro-beta-D-glycero-pentofuranosyl)-5-methylpyrimidine-2,4(1H,3H)-dione

2',3'-Anhydrothymidine

CAS: 14486-22-7

2',3'-Anhydrothymidine is a nucleoside analogue that has been shown to inhibit HIV-1 transcriptase and polymerase by binding to the enzyme's active site. It also inhibits DNA synthesis in human cells and inhibits the growth of E. coli. 2',3'-Anhydrothymidine is a prodrug that can be taken up by cells, where it is converted into an epoxide, which then binds to the enzyme's active site. This prevents the enzyme from catalyzing reactions and terminating DNA synthesis at the correct point during transcription. 2',3'-Anhydrothymidine may also have immunodeficiency-related benefits due to its ability to bind more tightly to dsDNA than natural nucleotides, causing termination of RNA synthesis at the wrong point.

Formula: C₁₀H₁₂N₂O₅

Purity: Min. 95%

Molecular weight: 240.21 g/mol

Ref: 3D-NA165900