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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:
41106305
PubChem Substance ID:
24884201
NACRES:
NA.22

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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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
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
Luděk Eyer et al.
Antimicrobial agents and chemotherapy, 65(2) (2020-11-25)
Emerging flaviviruses are causative agents of severe and life-threatening diseases, against which no approved therapies are available. Among the nucleoside analogues, which represent a promising group of potentially therapeutic compounds, fluorine-substituted nucleosides are characterized by unique structural and functional properties.
Z H Chen et al.
Molecular pharmacology, 52(5), 903-911 (1997-11-14)
5'-Deoxy-5'-methylthioadenosine phosphorylase (MTAP) is involved in the salvage of adenine and methylthio moieties of 5'-deoxy-5'-methylthioadenosine, a byproduct of polyamine synthesis, to adenine nucleotides and methionine, respectively. The gene encoding MTAP, MTAP, is frequently codeleted along with the tumor suppressor gene
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