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F9128

Sigma-Aldrich

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride

Synonym(s):

Adenosine-5′-(4-fluorosulfonylbenzoate) hydrochloride, FSBA

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About This Item

Empirical Formula (Hill Notation):
C17H16FN5O7S · HCl
CAS Number:
78859-42-4
Molecular Weight:
489.86
Beilstein/REAXYS Number:
8178939
MDL number:
MFCD00043258
UNSPSC Code:
41106305
PubChem Substance ID:
24894988
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

assay

≥95% (TLC)

form

powder

solubility

methanol: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

Cl[H].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COC(=O)c4ccc(cc4)S(F)(=O)=O)[C@@H](O)[C@H]3O

InChI

1S/C17H16FN5O7S.ClH/c18-31(27,28)9-3-1-8(2-4-9)17(26)29-5-10-12(24)13(25)16(30-10)23-7-22-11-14(19)20-6-21-15(11)23;/h1-4,6-7,10,12-13,16,24-25H,5H2,(H2,19,20,21);1H/t10-,12-,13-,16-;/m1./s1

InChI key

ZUHVYHQVJYIHPN-KHXPSBENSA-N

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Application

5′-(4-Fluorosulfonylbenzoyl)adenosine (FSBA) is an ATP analog used to study the mechanism of action of wortmannin. FSBA has been used to study vesicular transport in intestinal cells such as Caco-2, and to covalently modify residues in the nucleotide-binding domains (NBDs) of various ATPases, kinases, and other proteins.
5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride has been used to incubate with Ime2 (inducer of meiosis 2) to determine the sensitivity of Ime2 to the adenosine triphosphate (ATP) analog 5′-fluorosulfonylbenzoyladenosine (FSBA).

Biochem/physiol Actions

5′-(4-Fluorosulfonylbenzoyl)adenosine helps to recognize adenosine triphosphate (ATP)-binding sites in kinases due to its reaction with nucleophilic amino acids happening within these motifs.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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C Oudot et al.
European journal of biochemistry, 258(2), 579-585 (1999-01-05)
The ATPase activity of Escherichia coli isocitrate dehydrogenase kinase/phosphatase was rapidly lost after prior incubation with the ATP analogue 5'-[p-(fluorosulfonyl)benzoyl]adenosine (FSBA). This inactivation was prevented by the presence of either 5 mM ATP or 5 mM ADP plus Mg2+, while
Regalla Kumarswamy et al.
The international journal of biochemistry & cell biology, 41(6), 1430-1440 (2009-01-17)
Role of cytochrome-c in insect cell apoptosis is highly controversial, with many earlier reports suggesting lack of involvement of mitochondrial factors in Drosophila while more recent studies have indicated otherwise, thus warranting more in-depth studies of insect cell apoptosis. In
Selective Ion Tracing and MS n Analysis of Peptide Digests from FSBA-Treated Kinases for the Analysis of Protein ATP-Binding Sites
Renzone G, et al.
Journal of Proteome Research, 5(8), 2019-2024 (2006)
Xavier Hanoulle et al.
Journal of proteome research, 5(12), 3438-3445 (2006-12-02)
Adenine nucleotides are small, abundant molecules that bind numerous proteins involved in pivotal cellular processes. These nucleotides are co-factors or substrates for enzymes, regulators of protein function, or structural binding motifs. The identification of nucleotide-binding sites on a proteome-wide scale
Dinesh Manvar et al.
Biochemistry, 52(2), 432-444 (2012-12-28)
We have used an ATP analogue 5'-[p-(fluorosulfonyl)benzoyl]adenosine (FSBA) to modify HCV replicase in order to identify the ATP binding site in the enzyme. FSBA inactivates HCV replicase activity in a concentration-dependent manner with a binding stoichiometry of 2 moles of
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