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F9128

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride

Name: 5&#8242;-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride
Brand: SIGMA

≥95% (TLC), synthetic (organic), powder

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

NACRES:

NA.51

PubChem Substance ID:

24894988

UNSPSC Code:

41106305

MDL number:

MFCD00043258

Beilstein/REAXYS Number:

8178939

Assay:

≥95% (TLC)

Biological source:

synthetic (organic)

Form:

powder

Solubility:

methanol: 50 mg/mL, clear, colorless

Storage temp.:

−20°C

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Product Name

5′-(4-Fluorosulfonylbenzoyl)adenosine hydrochloride,

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

Application

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).

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.

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

GHS05

signalword

Danger

hcodes

H314

pcodes

P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000548794

0000342108

SLBX0795

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Inactivation of isocitrate dehydrogenase kinase/phosphatase by 5'-[p-(fluorosulfonyl)benzoyl]adenosine is not due to the labeling of the invariant lysine residue found in the protein kinase family.

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

Mitochondrial regulation of insect cell apoptosis: evidence for permeability transition pore-independent cytochrome-c release in the Lepidopteran Sf9 cells.

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)

Synthesis and characterization of 5'-p-fluorosulfonylbenzoyl-2' (or 3')-(biotinyl)adenosine as an activity-based probe for protein kinases.

Steven J Ratcliffe et al.

Journal of biomolecular screening, 12(1), 126-132 (2006-12-15)

Most of the kinase inhibitors that are approved for therapeutic uses or that are undergoing clinical trials are directed toward the adenosine triphosphate (ATP) binding site of protein kinases. 5'-Fluorosulfonylbenzoyl 5'-adenosine (FSBA) is an activitybased probe (ABP) that covalently modifies

A 5'-fluorosulfonylbenzoyladenosine-based method to identify physiological substrates of a Drosophila p21-activated kinase.

Nicolas Menzel et al.

Analytical biochemistry, 368(2), 178-184 (2007-06-29)

Nearly all processes in cells are regulated by the coordinated interplay between reversible protein phosphorylation and dephosphorylation. Therefore, it is a great challenge to identify all phosphorylation substrates of a single protein kinase to understand its integration into intracellular signaling

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Global Trade Item Number

SKU	GTIN
F9128-100MG	04061833048184
F9128-25MG	04061833048191
F9128-500MG	04061833048207

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