2'-Deoxy-2'-fluoroadenosine - CAS 64183-27-3

Name: 2'-Deoxy-2'-fluoroadenosine
Brand: BOC Sciences
Rating: 5 (1 reviews)

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

Technical Data

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