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F9128

Sigma-Aldrich

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C17H16FN5O7S · HCl
Numéro CAS:
78859-42-4
Poids moléculaire :
489.86
Numéro Beilstein :
8178939
Numéro MDL:
MFCD00043258
Code UNSPSC :
41106305
ID de substance PubChem :
24894988
Nomenclature NACRES :
NA.51

Source biologique

synthetic (organic)

Pureté

≥95% (TLC)

Forme

powder

Solubilité

methanol: 50 mg/mL, clear, colorless

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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).

Actions biochimiques/physiologiques

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.

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Eye Dam. 1 - Skin Corr. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

Sanjay S Khandekar et al.
Journal of biomolecular screening, 10(5), 447-455 (2005-08-12)
The currently approved kinase inhibitors for therapeutic uses and a number of kinase inhibitors that are undergoing clinical trials are directed toward the adenosine triphosphate (ATP) binding site of protein kinases. The 5'-fluorosulfonylbenzoyl 5'-adenosine (FSBA) is an ATP-affinity reagent that
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
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
Giovanni Renzone et al.
Proteins, 67(1), 189-197 (2007-01-24)
Sso7d from the extreme thermophilic crenarchaeon Sulfolobus solfataricus is a multifunctional protein in in vitro assays, whose in vivo role is still puzzling. Crystals of Sso7d in complex with DNA elucidated the protein surface involved in the binding to the
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