535087
2-Fluoroadenine
96%
Synonym(s):
2-Fluoro-7(9)H-purin-6-ylamine
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About This Item
Empirical Formula (Hill Notation):
C5H4FN5
CAS Number:
Molecular Weight:
153.12
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
assay
96%
mp
>350 °C (lit.)
functional group
fluoro
SMILES string
Nc1[nH]c(F)nc2ncnc12
InChI
1S/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)
InChI key
WKMPTBDYDNUJLF-UHFFFAOYSA-N
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Lincoln G Scott et al.
Journal of the American Chemical Society, 126(38), 11776-11777 (2004-09-24)
The production of isotopically labeled RNA remains critical to current NMR structural studies. One approach to obtain simple NMR spectra is to label with a nucleus that is not naturally occurring in RNA. Fluorine-19 can serve as a sensitive site-specific
V I Avramis et al.
Biochemical and biophysical research communications, 113(1), 35-43 (1983-05-31)
Murine P388 cells incubated in vitro with the anticancer drug arabinosyl 2-fluoroadenine accumulate its 5'-triphosphate, F-araATP, as the major phosphorylated metabolite. A new chromatographically separate metabolite that accumulated to levels 10% of that of F-araATP was identified as 2-fluoro-ATP, by
Sepideh Afshar et al.
Protein science : a publication of the Protein Society, 18(5), 1107-1114 (2009-04-24)
A double mutant of human purine nucleoside phosphorylase (hDM) with the amino acid mutations Glu201Gln:Asn243Asp cleaves adenosine-based prodrugs to their corresponding cytotoxic drugs. When fused to an anti-tumor targeting component, hDM is targeted to tumor cells, where it effectively catalyzes
Song Ye et al.
Nucleosides, nucleotides & nucleic acids, 22(10), 1899-1905 (2003-11-12)
A convenient synthesis of 2'-deoxy-2-fluoroadenosine from commercially available 2-fluoroadenine is described. The coupling reaction of silylated 2-fluoroadenine with phenyl 3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-1-thio-D-erythro-pentofuranoside gave the corresponding 2-fluoro-2'-deoxyadenosine derivative (alpha/beta = 1:1) in good yield. The alpha- and beta-anomers were separated by chromatography, and
X Y Wang et al.
Gene therapy, 11(21), 1559-1567 (2004-09-03)
Gene-directed enzyme prodrug therapy (GDEPT) based on the Escherichia coli enzyme, purine nucleoside phosphorylase (PNP), provides a novel strategy for treating slowly growing tumors like prostate cancer (CaP). PNP converts systemically administered prodrug, fludarabine phosphate, to a toxic metabolite, 2-fluoroadenine
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