151006-30-3

Usage

InChI:InChI=1/C10H16N5O6P/c11-10-13-8-7(9(17)14-10)12-4-15(8)5-21-6(3-16)1-2-22(18,19)20/h4,6,16H,1-3,5H2,(H2,18,19,20)(H3,11,13,14,17)/t6-/m1/s1

Upstream product

• 150943-39-8 (R)-2-((2-acetamido-1,6-dihydro-6-oxo-7H-purin-7-yl)methoxy)-4-chlorobutyl benzoate 
• 150943-37-6 (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane 
• 150943-38-7 (R)-4-chloro-2-(methoxymethoxy)butyl benzoate 
• 3056-33-5 2,9-diacetylguanine 
• 266344-94-9 (R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutylphosphonic acid monophosphate 
• 156721-88-9 (R)-diethyl <3-((2-acetamido-1,6-dihydro-6-oxo-7H-purin-7-yl)methoxy)-4-(benzoyloxy)butyl>phosphonate 

Relevant academic research and scientific papers

Phosphorylation of ganciclovir phosphonate by cellular GMP kinase determines the stereoselectivity of anti-human cytomegalovirus activity

A racemic mixture of ganciclovir phosphonate was resolved by stereoselective phosphorylation using GMP kinase. The R-enantiomer of ganciclovir phosphonate was active against human cytomegalovirus but the S- enantiomer was less active. We show that enantiomeric selectivity of antiviral activity for ganciclovir phosphonate was conferred by stereoselective phosphorylations by mammalian enzymes, not by stereoslective inhibition of DNA polymerase from human cytomegalovirus.

An enantiospecific synthesis of the human cytomegalovirus antiviral agent [(R)-3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4- hydroxybutyl]phosphonic acid

The racemic isosteric phosphonate of ganciclovir monophosphate (BW2482U89, SR3745, [3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4- hydroxybutyl]phosphonic acid, 1) has potent and selective in vitro activity against human cytomegalovirus. An enant