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F9128

Sigma-Aldrich

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride

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Synonym(s):
Adenosine-5′-(4-fluorosulfonylbenzoate) hydrochloride, FSBA
Empirical Formula (Hill Notation):
C17H16FN5O7S · HCl
CAS Number:
Molecular Weight:
489.86
Beilstein:
8178939
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

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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This Item
A5638D8013A9501
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

assay

≥95% (TLC)

assay

≥95%

assay

≥95% (HPLC)

assay

≥98.5% (HPLC)

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

methanol: 50 mg/mL, clear, colorless

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

solubility

H2O: 50 mg/mL

solubility

H2O: 10 mg/mL, clear, colorless (pH of aqueous solution is approx. 3.0. The sodium salt (A6885) is about 20× more soluble.)

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

Signal Word

Danger

Hazard Statements

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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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)
E J Mueller et al.
Biochemistry, 38(31), 9831-9839 (1999-08-06)
Aminoimidazole ribonucleotide (AIR) synthetase (PurM) catalyzes the conversion of formylglycinamide ribonucleotide (FGAM) and ATP to AIR, ADP, and P(i), the fifth step in de novo purine biosynthesis. The ATP binding domain of the E. coli enzyme has been investigated using
Purification and some properties of Saccharomyces cerevisiae meiosis-specific protein kinase Ime2
Hui CM, et al.
Protein Expression and Purification, 26(3), 416-424 (2002)
Alberto Guevara-Flores et al.
Molecular and biochemical parasitology, 162(2), 123-133 (2008-09-04)
The tegumental membrane of Taenia crassiceps cysticerci contains an ATP-diphosphohydrolase (EC 3.6.1.5) which hydrolyzes purine and pyrimidine nucleoside 5'-di- and 5'-triphosphates at an optimum pH of 8.5. It is Mg(2+)-dependent and insensitive to classical ATPase and phosphatase inhibitors. In solubilized

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