22837-44-1

Basic information

• Product Name: 2'-Deoxy-L-guanosine
• Synonyms: 2-AMino-9-((2R,4R,5S)-4-hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one;2-Amino-9-(2-deoxy-beta-L-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one;9-(2-Deoxy-beta-L-erythro-pentofuranosyl)guanine;L-2'-deoxyguanosine
• CAS NO: 22837-44-1
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 266.256
• EINECS: 500-100-4
• Mol File: 22837-44-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 2.08±0.1 g/cm3(Predicted)
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: 2'-Deoxy-L-guanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Deoxy-L-guanosine(22837-44-1)
• EPA Substance Registry System: 2'-Deoxy-L-guanosine(22837-44-1)

Safety Data

• Hazardous Substances Data: 22837-44-1(Hazardous Substances Data)

Usage

Description

2'-Deoxy-L-guanosine is a nucleoside that shows antibiotic properties by inhibiting protein synthesis, leading to cell death. This is done by binding to the ribose phosphate backbone of DNA, phosphorylating it, and preventing the base pairing of adenosine with thymine. 2'-Deoxy-L-guanosine shows a high level of resistance against bacteria and is effective in the treatment of gram-positive bacteria.

Upstream product

• 31615-99-3 3',5'-dibenzoyl-2'-deoxy-β-L-uridine 
• 21047-87-0 N²-palmytoylguanine 
• 144224-72-6 3',5'-di-O-benzoyl-2'-deoxy-β-L-N²-palmitoylguanosine 

Downstream Products

• 1312300-90-5 C₃₇H₄₃N₅O₆Si 
• 1312300-83-6 C₃₇H₄₅N₅O₆Si 
• 141771-80-4 N-(9-{(2S,4R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide 
• 5614-64-2 8-oxo-7,8-dihydroguanine 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 

Relevant articles and documents

L-thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth

We have demonstrated that herpes simplex 1 (HSV1) thymidine kinase (TK) shows no stereospecificity for D- and L-β-nucleosides. In vitro, L enantiomers are not recognized by human TK, but function as specific substrates for the viral enzyme in the order: L-thymidine (L-T) >> 2'-deoxy- L-guanosine (L-dG) > 2'-deoxy-L-uridine (L-dU) > 2'-deoxy-L-cytidine (L-dC) > 2'-deoxy-L-adenosine (L-dA). HSV1 TK phosphorylates both thymidine enantiomers to their corresponding monophosphates with identical efficiency and the K(i) of L-T (2 μM) is almost identical to the K(m) for the natural substrate D-T (2.8 μM). The L enantiomer reduces the incorporation of exogenous [3H]T into cellular DNA in HeLa TK-/HSV1 TK+ but not in wild-type HeLa cells, without affecting RNA, protein synthesis, cell growth, and viability. L-T markedly reduces HSV1 multiplication in HeLa cells. Our observations could lead to the development of a novel class of antiviral drugs characterized by low toxicity.