434936-88-6

Basic information

• Product Name: 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one
• Synonyms: 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one
• CAS NO: 434936-88-6
• Molecular Weight: 553.615
• Mol File: 434936-88-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one(434936-88-6)
• EPA Substance Registry System: 7-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-β-D-ribofuranosyl}imidazo[1,2-a]pyrazin-8(7H)-one(434936-88-6)

Safety Data

• Hazardous Substances Data: 434936-88-6(Hazardous Substances Data)

Upstream product

• 434936-86-4 7-(3',5'-di-O-acetyl-2'-deoxy-D-ribofuranosyl)imidazo[1,2-a]pyrazin-8(7H)-one 
• 151767-35-0 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 434936-87-5 7-(2'-deoxy-D-ribofuranosyl)imidazo[1,2-a]pyrazin-8(7H)-one 
• 434936-84-2 1-(2,2-diethoxyethyl)-1H-imidazole-2-carboxamide 
• 434936-85-3 Imidazo[1,2-a]pyrazin-8(7H)-one 

Relevant articles and documents

Evaluation of novel third-strand bases for the recognition of a C·G base pair in the parallel DNA triple-helical binding motif

We describe the synthesis and the incorporation into oligonucleotides of the novel nucleoside building blocks 9, 10, and 16, carrying purine-like double H-bond-acceptor bases. These base-modified nucleosides were conceived to recognize selectively a cytosine · guanine (C·G) inversion site within a homopurine · homopyrimidine duplex, when constituent of a DNA third strand designed to bind in the parallel binding motif. While building block 16 turned out to be incompatible with standard oligonucleotide-synthesis conditions, UV/triplex melting experiments with third-strand 15-mers containing β-D-nucleoside 6 (from 9) showed that recognition of the four natural Watson-Crick base pairs follows the order G·C ? C·G > A· T> T·A. The recognition is sequence-context sensitive, and G·C or C·G recognition does not involve protonated species of β-D-nucleoside 6. The data obtained fit (but do not prove) a structural model for C · G recognition via one conventional and one C - H··· O H-bond. The unexpected G · C recognition is best explained by third-strand base intercalation. A comparison of the triplex binding properties of these new bases with those of 4-deoxothymine (5-methylpyrimidine-2(1H)-one, 4HT), previously shown to be C·G selective but energetically weak, is also described.