68045-42-1

Basic information

• Product Name: Guanosine, 2'-deoxy-, O-methyloxime
• CAS NO: 68045-42-1
• Molecular Formula: C11H16N6O4
• Molecular Weight: 296.286
• Mol File: 68045-42-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Guanosine, 2'-deoxy-, O-methyloxime(CAS DataBase Reference)
• NIST Chemistry Reference: Guanosine, 2'-deoxy-, O-methyloxime(68045-42-1)
• EPA Substance Registry System: Guanosine, 2'-deoxy-, O-methyloxime(68045-42-1)

Safety Data

• Hazardous Substances Data: 68045-42-1(Hazardous Substances Data)

Usage

General Description

Guanosine, 2'-deoxy-, O-methyloxime is a modified form of guanosine, a nucleoside that serves as one of the building blocks for DNA and RNA. The O-methyloxime modification involves the addition of a methyl group to the oxygen atom of the oxime functional group, which alters the chemical and biological properties of guanosine. This modification is often used in the development of nucleoside analogs for drug discovery and chemical biology research. Guanosine, 2'-deoxy-, O-methyloxime has potential applications in the development of new pharmaceuticals and as a tool in studying nucleic acid structure and function.

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 35095-93-3 2-Amino-6-chloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)purine 
• 136986-34-0 2-amino-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranosyl)-6-methoxyaminopurine 

Downstream Products

• 869354-99-4 N'-{9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine 
• 136986-36-2 N'-{9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-[(Z)-methoxyimino]-6,9-dihydro-1H-purin-2-yl}-N,N-dimethyl-formamidine 
• 136986-37-3 9-<2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl>-2-dimethyleneamino-6-methoxyaminopurine 3'-(2-cyanoethyl N,N-di-isopropylphosphoramidite) 

Relevant articles and documents

Synthesis and duplex stability of oligonucleotides containing adenine-guanine analogues

The nucleosides N6-methoxy-2'-deoxyadenosine (dZ) and 2-amino-9-(2-deoxy-β-ribofuranosyl)-6-methoxyaminopurine (dK) have been synthesised and converted into 5'-O-dimethoxytrityl 3'-(2-cyanoethyl N,N-diisopropylphosphoramidites). These monomers have been used in machine DNA synthesis to give a set of heptadecanucleotides containing up to three analogue nucleotides. The melting transitions (T(m) show that the 17-mer duplexes containing Z·T and Z·C base-pairs have closely similar stabilities, as have those containing K·T and K·C pairs. They are less stable than the corresponding fully complementary duplexes, but more stable than those containing mismatched pairs. This, in the case of dZ, is in accord with the amino-imino tautomeric ratio of ~1:4 observed for the nucleoside in methyl sulfoxide. The application of oligomers containing such 'degenerate' bases in oligonucleotide probes and primers is discussed. The nucleosides N6-methoxy-2′-deoxyadenosine (dZ) and 2-amino-9-(2-deoxy-β-ribofuranosyl)-6-methoxyaminopurine (dK) have been synthesised and converted into 5′-O-dimethoxytrityl 3′-(2-cyanoethyl N,N-diisopropylphosphoramidites). These monomers have been used in machine DNA synthesis to give a set of heptadecanucleotides containing up to three analogue nucleotides. The melting transitions (Tm) show that the 17-mer duplexes containing Z·T and Z·C base-pairs have closely similar stabilities, as have those containing K·T and K·C pairs. They are less stable than the corresponding fully complementary duplexes, but more stable than those containing mismatched pairs. This, in the case of dZ, is in accord with the amino-imino tautomeric ratio of approximately 1:4 observed for the nucleoside in methyl sulfoxide. The application of oligomers containing such 'degenerate' bases in oligonucleotide probes and primers is discussed.