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B3131

Sigma-Aldrich

8-Bromoadenosine 5′-monophosphate

≥98%

Synonym(s):

8-Br-AMP

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About This Item

Empirical Formula (Hill Notation):
C10H13BrN5O7P
CAS Number:
23567-96-6
Molecular Weight:
426.12
MDL number:
MFCD00056945
UNSPSC Code:
41106305
PubChem Substance ID:
24891684
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

Assay

≥98%

form

powder

solubility

water: 100 mg/mL, clear, colorless

storage temp.

−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)

InChI key

DNPIJKNXFSPNNY-UHFFFAOYSA-N

Related Categories

Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
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
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
Gijs Teklenburg et al.
PloS one, 7(3), e32701-e32701 (2012-03-14)
Female mammals inactivate one of their two X-chromosomes to compensate for the difference in gene-dosage with males that have just one X-chromosome. X-chromosome inactivation is initiated by the expression of the non-coding RNA Xist, which coats the X-chromosome in cis
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