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B3131

Sigma-Aldrich

8-Bromoadenosine 5′-monophosphate

≥98%

Synonym(e):

8-Br-AMP

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About This Item

Empirische Formel (Hill-System):
C10H13BrN5O7P
CAS-Nummer:
23567-96-6
Molekulargewicht:
426.12
MDL-Nummer:
MFCD00056945
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24891684
NACRES:
NA.51

Biologische Quelle

synthetic (organic)

Qualitätsniveau

200

Assay

≥98%

Form

powder

Löslichkeit

water: 100 mg/mL, clear, colorless

Lagertemp.

−20°C

SMILES String

Nc1ncnc2n(C3OC(COP(O)(O)=O)C(O)C3O)c(Br)nc12

InChI

1S/C10H13BrN5O7P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,13,14)(H2,19,20,21)

InChIKey

DNPIJKNXFSPNNY-UHFFFAOYSA-N

Verwandte Kategorien

Anwendung

8-Bromoadenosine 5′′-monophosphate (8-Br-AMP) is an analogue of 5′-AMP useful for receptor mapping studies; as a starting structure for 8-modified 5′-AMP derivatives and for synthesis of poly-8-bromoriboadenylic acid.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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K Lesiak et al.
Biochemical and biophysical research communications, 126(2), 917-921 (1985-01-31)
When added to extracts of mouse L cells containing ATP and an energy regenerating system, the 5'-diphosphate of 2-5A core, pp5'A2'p5'A2'p5'A, as well as a bromoadenylate analog, pp5' (br8A)2'p5'(br8A)2'p5'(br8A), can be phosphorylated to the corresponding 5'-triphosphate, ppp5'A2'p5'A2'p5'A and ppp5'(br8A)2'p5'(br8A)2'p5(br8A), respectively.
Rongkuan Hu et al.
PloS one, 8(8), e73527-e73527 (2013-08-24)
This study is the first to demonstrate that shizukaol D, a natural compound isolated from Chloranthusjaponicus, can activate AMP- activated protein kinase (AMPK), a key sensor and regulator of intracellular energy metabolism, leading to a decrease in triglyceride and cholesterol
J O Folayan et al.
Journal of biochemistry, 96(4), 1297-1301 (1984-10-01)
Poly-8-bromoriboadenylic acid was synthesized by the bromination of adenosine-5'-monophosphate to yield 8-bromoadenosine-5'-monophosphate which on conversion to the 5'-diphosphate form was polymerized by polynucleotide phosphorylase (PNPase). The polymer formed a 1:1 hybrid with polyribouridylic acid and the hybrid was found to
Guido Michels et al.
PloS one, 3(1), e1511-e1511 (2008-01-31)
Hyperpolarization-activated, cyclic nucleotide sensitive (HCN) channels underlie the pacemaker current I(f), which plays an essential role in spontaneous cardiac activity. HCN channel subunits (HCN1-4) are believed to be modulated by additional regulatory proteins, which still have to be identified. Using
E N Kanaya et al.
Biochemistry, 23(18), 4219-4225 (1984-08-28)
Introduction of the bulky 8-bromo substituent into adenine residues of polynucleotides has strikingly different consequences in the deoxy- and ribopolynucleotide series. Poly(r8BrA) was found in earlier studies to form a very stable double-helical self-structure but not to undergo interaction with
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