91702-60-2

Basic information

• Product Name: Acyclovir EP Impurity M
• Synonyms: Acyclovir EP Impurity M
• CAS NO: 91702-60-2
• Molecular Formula: C₁₂H₁₅N₅O₅
• Molecular Weight: 309.278
• Mol File: 91702-60-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acyclovir EP Impurity M(CAS DataBase Reference)
• NIST Chemistry Reference: Acyclovir EP Impurity M(91702-60-2)
• EPA Substance Registry System: Acyclovir EP Impurity M(91702-60-2)

Safety Data

• Hazardous Substances Data: 91702-60-2(Hazardous Substances Data)

Usage

Uses

An impurity of Acyclovir. Aciclovir EP Impurity M

Upstream product

• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 59278-00-1 2-acetoxyethyl acetoxymethyl ether 
• 108-24-7 acetic anhydride 
• 109-86-4 2-methoxy-ethanol 
• 3056-33-5 2,9-diacetylguanine 
• 646-06-0 1,3-DIOXOLANE 
• 118-00-3 G 
• 30747-22-9 N²-acetyl-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)guanine 
• 30747-23-0 Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 
• 102728-65-4 Acetic acid 2-(2-oxo-propoxy)-ethyl ester 

Downstream Products

• 75128-73-3 2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one 
• 91702-61-3 7-(2-Hydroxyethoxymethyl)guanine 

Relevant articles and documents

Engineering a selective small-molecule substrate binding site into a deoxyribozyme

A small goal: An RNA ligase deoxyribozyme is engineered to accept a small-molecule NTP substrate in a multiple-turnover fashion. Selective binding is enforced by hydrogen bonding, and structural preorganization within the NTP itself is important for its efficient utilization as a substrate. This study points the way toward a broader use of small-molecule substrates with nucleic acid enzymes. (Figure Presented)

Regioselective synthesis of acyclovir and its various prodrugs

High-yield regioselective synthesis of 9-[(2-hydroxyethoxy)methyl]guanine (Acyclovir 1, Scheme 1) was achieved from guanine via trisilylated guanine. N2-acylacyclovir 9a-9b were prepared from N2, O-diacylacyclovir (4, 8b-8d) using regioselective deacylation procedure. N2-Acylacyclovir 11 and 13 were prepared via protection of primary hydroxyl groups. Three amino acid esters of acyclovir were synthesized as water-soluble prodrugs, which form protonated cations in pH 7.4 phosphate buffer. Two water-soluble ester prodrugs with free carboxylic acids, which form anionic species in pH 7.4 phosphate buffer, were also synthesized.

Regioselectivity and mechanism of transpurination reactions in the guanine nucleosides series

The transpurination reaction of the fully acetylated derivatives of guanosine and its 7-β-D-ribofuranosyl regioisomer with 2-acetoxyethyl acetoxymethyl ether has been studied using high performance liquid chromatography (HPLC). The regioselectivity of glycosyl exchange observed in the early stages of the reaction suggests that the unsubstituted nitrogen atoms of the imidazole portion (N7 and N9) are, exclusively, sites of direct glycosylation in the case of guanine derivatives. The results lead to the conclusion that the mechanism of the glycosylation reaction of guanine is different to that of adenine.