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F9128

Sigma-Aldrich

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride

Synonym(s):

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

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25 MG
€619.00
100 MG
€1,900.00
500 MG
€7,490.00

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25 MG
€619.00
100 MG
€1,900.00
500 MG
€7,490.00

About This Item

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

€619.00

Please contact Customer Service for Availability

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).[1]

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.[2]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000342108
0000342108
SLBX0795
SLBS7663
SLBN9061V

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P Borowski et al.
Biological chemistry, 380(4), 403-412 (1999-06-04)
A detergent extract isolated from the enriched fraction of integral membrane proteins of Jurkat cells showed an enhanced tyrosine phosphate level when phosphorylated in the presence of phorbol 12-myristate 13-acetate (TPA) and phorbol 12,13-dibutyrate (PDBu). The enhanced tyrosine phosphorylation was
Kenichi A Tanaka et al.
Platelets, 15(5), 325-332 (2004-09-17)
The use of clopidogrel (Plavix), an inhibitor of adenosine diphosphate (ADP)-induced platelet aggregation, has been proven to reduce ischemic events in cardiovascular patients, but little information is available for optimal monitoring of platelet function in patients receiving the drug preoperatively.
Eric Faudry et al.
The Journal of biological chemistry, 279(19), 19607-19613 (2004-02-27)
Apyrases are nucleoside triphosphate-diphosphohydrolases (EC 3.6.1.5) present in a variety of organisms. The apyrase activity found in the saliva of hematophagous insects is correlated with the prevention of ADP-induced platelet aggregation of the host during blood sucking. Purification of apyrase
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
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
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