2'-Deoxy-2'-fluoroadenosine - CAS 64183-27-3
Catalog: |
BB032393 |
Product Name: |
2'-Deoxy-2'-fluoroadenosine |
CAS: |
64183-27-3 |
Synonyms: |
2'-Fluoro Adenosine; 2'-Fluoro-2'-deoxyadenosine; (2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol; 9-(2-Fluoro-2-deoxy-beta-D-ribofuranosyl)-purin-6-amine; 9-(2-Deoxy-2-fluoro-beta-D-ribofuranosyl)adenine; 6-Amino-9-(2-deoxy-2-fluoro-beta-D-ribofuranosyl)-9H-purine; 2'-F-dA |
IUPAC Name: | (2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol |
Description: | 2'-Deoxy-2'-fluoroadenosine is a modified nucleoside where a fluorine atom is substituted at the 2' position of the ribose sugar in adenosine. This modification enhances the stability and alters the biochemical properties of the nucleoside. It is used in studying nucleotide metabolism, enzymatic reactions involving nucleosides, and exploring nucleic acid-protein interactions. |
Molecular Weight: | 269.23 |
Molecular Formula: | C10H12FN5O3 |
Canonical SMILES: | C1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CO)O)F |
InChI: | InChI=1S/C10H12FN5O3/c11-5-7(18)4(1-17)19-10(5)16-3-15-6-8(12)13-2-14-9(6)16/h2-5,7,10,17-18H,1H2,(H2,12,13,14)/t4-,5-,7-,10-/m1/s1 |
InChI Key: | ZGYYPTJWJBEXBC-QYYRPYCUSA-N |
Boiling Point: | 628.6±65.0 °C (Predicted) |
Melting Point: | 228-231 °C |
Purity: | ≥95% |
Density: | 2.01±0.1 g/cm3 (Predicted) |
Solubility: | Soluble in Acetonitrile (Slightly), Methanol (Slightly, Heated) |
Appearance: | White to off-white solid |
Storage: | Store at -20 °C under inert atmosphere |
MDL: | MFCD09750859 |
LogP: | -0.42160 |
GHS Hazard Statement: | H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
Precautionary Statement: | P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501 |
Signal Word: | Warning |
Publication Number | Title | Priority Date |
WO-2021203043-A2 | Targeted inhibition using engineered oligonucleotides | 20200402 |
CN-111534493-A | Purine nucleoside phosphorylase mutant, gene and application | 20200401 |
WO-2021178209-A1 | Aptamers and use thereof | 20200303 |
WO-2021152146-A1 | Process for the production of closed linear dna | 20200131 |
WO-2021152147-A1 | Closed linear dna with modified nucleotides | 20200131 |
PMID | Publication Date | Title | Journal |
22579483 | 20120615 | S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine | Bioorganic & medicinal chemistry letters |
20532912 | 20100901 | Susceptibility in vitro of clinically metronidazole-resistant Trichomonas vaginalis to nitazoxanide, toyocamycin, and 2-fluoro-2'-deoxyadenosine | Parasitology research |
19388075 | 20090501 | Structure of a mutant human purine nucleoside phosphorylase with the prodrug, 2-fluoro-2'-deoxyadenosine and the cytotoxic drug, 2-fluoroadenine | Protein science : a publication of the Protein Society |
18026095 | 20080101 | Unnatural substrates reveal the importance of 8-oxoguanine for in vivo mismatch repair by MutY | Nature chemical biology |
16245934 | 20051101 | Insight into the roles of tyrosine 82 and glycine 253 in the Escherichia coli adenine glycosylase MutY | Biochemistry |
Complexity: | 338 |
Compound Is Canonicalized: | Yes |
Covalently-Bonded Unit Count: | 1 |
Defined Atom Stereocenter Count: | 4 |
Defined Bond Stereocenter Count: | 0 |
Exact Mass: | 269.09241742 |
Formal Charge: | 0 |
Heavy Atom Count: | 19 |
Hydrogen Bond Acceptor Count: | 8 |
Hydrogen Bond Donor Count: | 3 |
Isotope Atom Count: | 0 |
Monoisotopic Mass: | 269.09241742 |
Rotatable Bond Count: | 2 |
Topological Polar Surface Area: | 119 Å2 |
Undefined Atom Stereocenter Count: | 0 |
Undefined Bond Stereocenter Count: | 0 |
XLogP3: | 0 |
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