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656402

Sigma-Aldrich

2-Fluoroadenosine

97%

Synonym(s):

2-Fluoro-9-β-D-ribofuranosyladenine

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About This Item

Empirical Formula (Hill Notation):
C10H12FN5O4
CAS Number:
146-78-1
Molecular Weight:
285.23
MDL number:
MFCD00866394
UNSPSC Code:
12352200
PubChem Substance ID:
24884201
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

mp

240 °C (D) (lit.)

SMILES string

Nc1nc(F)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1

InChI key

HBUBKKRHXORPQB-UUOKFMHZSA-N

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

Related Categories

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - 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, Faceshields, Gloves

Certificates of Analysis (COA)

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U K Decking et al.
The American journal of physiology, 266(4 Pt 2), H1596-H1603 (1994-04-01)
Transport and phosphorylation of 2-fluoroadenosine (F-AR) were studied in human erythrocytes and porcine aortic endothelial cells by 19F-nuclear magnetic resonance (NMR) spectroscopy. F-AR (590 microM) added to a human erythrocyte suspension (15% hematocrit) was rapidly incorporated into adenine nucleotides at
M L Deras et al.
Biochemistry, 38(1), 303-310 (1999-01-16)
In contrast to several other glutamine amidotransferases including asparagine synthetase, cytidine 5'-triphosphate (CTP) synthetase, carbamoyl phosphate synthetase, and phosphoribosyl pyrophosphate (PRPP) amidotransferase, guanosine monophosphate synthetase (GMPS) will not utilize hydroxylamine as an alternative nitrogen source. Instead, the enzyme is inhibited
Larissa Romanello et al.
Acta crystallographica. Section D, Biological crystallography, 69(Pt 1), 126-136 (2013-01-01)
In adult schistosomes, the enzyme adenosine kinase (AK) is responsible for the incorporation of some adenosine analogues, such as 2-fluoroadenosine and tubercidin, into the nucleotide pool, but not others. In the present study, the structures of four complexes of Schistosoma
V B Berzin et al.
Bioorganicheskaia khimiia, 35(2), 210-214 (2009-06-20)
The preparative method for the synthesis of 2-fluoroadenosine starting from commercially available guanosine was developed. It included the intermediate formation of 2-amino-6-azido-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine, which was isolated exclusively in the tetrazolo[5,1-i]-form {5-amino-7-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-7H-tetrazolo[5,1-i]purine}. The latter compound was converted by the Schiemann reaction to
Mian M Alauddin et al.
Nuclear medicine and biology, 34(3), 267-272 (2007-03-27)
Many fluorinated analogues of adenosine nucleoside have been synthesized and studied as potential antitumor and antiviral agents. Earlier, we reported radiosynthesis of 2'-deoxy-2'-[(18)F]fluoro-1-beta-D-arabinofuranosyl-adenine ([(18)F]-FAA) and 3'-deoxy-3'-[(18)F]fluoro-1-beta-d-xylofuranosyl-adenine ([(18)F]FXA). Now, we report their in vivo studies including blood clearance, biodistribution and micro-PET
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