180477-26-3

Basic information

• Product Name: 2-amino-8-<5-O--2-deoxy-β-D-erythro-pentofuranosyl>-8H-imidazo<1,2-a><1,3,5>triazin-4-one
• Synonyms: 2-amino-8-<5-O--2-deoxy-β-D-erythro-pentofuranosyl>-8H-imidazo<1,2-a><1,3,5>triazin-4-one
• CAS NO: 180477-26-3
• Molecular Weight: 569.617
• Mol File: 180477-26-3.mol

Chemical Properties

• CAS DataBase Reference: 2-amino-8-<5-O--2-deoxy-β-D-erythro-pentofuranosyl>-8H-imidazo<1,2-a><1,3,5>triazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-8-<5-O--2-deoxy-β-D-erythro-pentofuranosyl>-8H-imidazo<1,2-a><1,3,5>triazin-4-one(180477-26-3)
• EPA Substance Registry System: 2-amino-8-<5-O--2-deoxy-β-D-erythro-pentofuranosyl>-8H-imidazo<1,2-a><1,3,5>triazin-4-one(180477-26-3)

Safety Data

• Hazardous Substances Data: 180477-26-3(Hazardous Substances Data)

Upstream product

• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 110457-87-9 2-amino-8-(2-deoxy-β-D-erythro-pentofuranosyl)-8H-imidazo[1,2-a]-s-triazin-4-one 

Relevant articles and documents

5-Aza-7-deaza-2'-deoxyguanosine: Oligonucleotide duplexes with novel base pairs, parallel chain orientation and protonation sites in the core of a double helix

Oligonucleotides containing 5-aza-7-deaza-2'-deoxyguanosine (1) were synthesized. Solid-phase synthesis was performed with the phosphonate 15 or the phosphoramidite 5. The amino-unprotected phosphonate 4 was also employed. Hybridization studies of oligonucleotides containing 1 resulted in new base pairs leading to duplexes with parallel (ps) or antiparallel (aps) chain orientation. Among those with parallel chains a stable 'purine-purine' base pair was observed between 5-aza-7-deazaguanine and guanine or 7-deazaguanine. Antiparallel stranded duplexes are formed when 5-aza-7-deazaguanine pairs with cytosine. This base pair has only two hydrogen bonds under neutral conditions but is stabilized by a third one in acidic medium. A new base pair is also detected between the base of 1 and isoguanine (neutral medium).

Parallel-stranded duplex DNA formed by a new base pair between guanine and 5-aza-7-deazaguanine

Oligonucleotides containing 5-aza-7-deazaguanine residues have been synthesized. A DNA duplex with parallel strand orientation is assembled by a new base pair between guanine and 5-aza-7-deazaguanine.

Parallel-stranded DNA formed by new base pairs related to the isoguanine-cytosine or isocytosine-guanine motifs

Parallel-stranded (ps) oligonucleotide duplexes containing several new base pairs formed between 7-deazaisoguanine and cytosine, 8-aza-7-deaza- isoguanine and cytosine, and 5-aza-7-deaza guanine and guanine are described. The stability of the ps-hybrids increased if the duplex contains 8-aza-7- deazaisoguanine instead of isoguanine and is decreased by 7-deazaisoguanine incorporation. The purine-purine base pair between 5-aza-7-deazaguanine and guanine was found to be more stable than that of 5-methylisocytosine with guanine.