23567-96-6

Basic information

• Product Name: 8-BROMOADENOSINE 5'-MONOPHOSPHATE
• Synonyms: 8-BROMOADENOSINE 5'-MONOPHOSPHATE;8-bromoadenosine 5'-monophosphate*free acid;8-Bromoadenosine 5'-(dihydrogen phosphate);Adenosine, 8-bromo-, 5'-(dihydrogen phosphate);8-Br-AMP
• CAS NO: 23567-96-6
• Molecular Formula: C₁₀H₁₃BrN₅O₇P
• Molecular Weight: 426.12
• Product Categories: Biochemicals and Reagents;Nucleosides, Nucleotides, Oligonucleotides;Nucleotide Analogs
• Mol File: 23567-96-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 834.8°Cat760mmHg
• Flash Point: 458.7°C
• Appearance: /
• Density: 2.62g/cm³
• Storage Temp.: −20°C
• CAS DataBase Reference: 8-BROMOADENOSINE 5'-MONOPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-BROMOADENOSINE 5'-MONOPHOSPHATE(23567-96-6)
• EPA Substance Registry System: 8-BROMOADENOSINE 5'-MONOPHOSPHATE(23567-96-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23567-96-6(Hazardous Substances Data)

Usage

Description

8-BROMOADENOSINE 5'-MONOPHOSPHATE, also known as 8-Br-AMP, is a chemical compound and an analogue of 5'-AMP (adenosine 5'-monophosphate). It is characterized by the presence of a bromine atom at the 8th position of the adenine base, which distinguishes it from the naturally occurring 5'-AMP. This modification provides unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical and Biochemical Research:
8-BROMOADENOSINE 5'-MONOPHOSPHATE is used as a research tool for receptor mapping studies, allowing scientists to investigate the interactions between adenosine receptors and their ligands. This helps in understanding the role of adenosine receptors in various physiological processes and their potential as therapeutic targets.
Used in Synthesis of Modified Nucleotides:
8-BROMOADENOSINE 5'-MONOPHOSPHATE serves as a starting structure for the synthesis of 8-modified 5'-AMP derivatives. These modified nucleotides can be used in the development of new drugs, particularly in the field of antiviral and anticancer therapies, as they may exhibit altered binding properties and enhanced activity compared to the native nucleotides.
Used in Polymer Synthesis:
8-BROMOADENOSINE 5'-MONOPHOSPHATE is also used in the synthesis of poly-8-bromoriboadenylic acid, a modified nucleic acid polymer. This polymer may have potential applications in the development of novel materials with specific properties, such as improved stability or altered interactions with other biomolecules.

Upstream product

• 2946-39-6 8-bromoadenosine 
• 61-19-8 5'-adenosine monophosphate 

Downstream Products

• 1018828-91-5 8-phenyl-adenosine 5'-monophosphate morpholidate 
• 1018828-98-2 8-phenyl NAD 
• 1352621-63-6 C₂₆H₃₆N₇O₉P 
• 1352621-54-5 8-(3-(Boc-aminomethyl)phenyl) NAD 
• 1352621-58-9 8-(3-(Boc-aminomethyl)phenyl)adenosine 5'-monophosphate 
• 1018828-70-0 8-(phenyl)adenosine 5'-monophosphate 
• 25030-04-0 8-oxyadenosine 5'-monophosphate 
• 78711-08-7 8-(benzylamino)inosine 5'-phosphate 
• 84877-20-3 p5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A) 
• 100899-86-3 p5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A) 
• 84311-64-8 p5'(br⁸A)2'p5'(br⁸A)2'p5'(br⁸A) 
• 78710-98-2 8-benzylamine-adenosine-5-monophosphate 
• 78710-88-0 Phosphoric acid mono-{(2R,3S,4R,5R)-5-[6-amino-8-(4-chloro-benzylsulfanyl)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl} ester 
• 78710-84-6 8-(4-chlorophenylthio)adenosine-5’-O-monophosphate 

Relevant articles and documents

Studies of nucleosides and nucleotides. XXXIX. Synthesis of 8-substituted purine nucleotides by the direct replacement reactions.

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Variable-Temperature NMR Spectroscopy, Conformational Analysis, and Thermodynamic Parameters of Cyclic Adenosine 5′-Diphosphate Ribose Agonists and Antagonists

Cyclic adenosine 5′-diphosphate ribose (cADPR) is a ubiquitous Ca2+-releasing second messenger. Knowledge of its conformational landscape is an essential tool for unraveling the structure-activity relationship (SAR) in cADPR. Variable-temperature 1H NMR spectroscopy, in conjunction with PSEUROT and population analyses, allowed us to determine the conformations and thermodynamic parameters of the furanose rings, γ-bonds (C4′-C5′), and β-bonds (C5′-O5′) in the cADPR analogues 2′-deoxy-cADPR, 7-deaza-cADPR, and 8-bromo-cADPR. A significant finding was that, although the analogues are similar to each other and to cADPR itself in terms of overall conformation and population (ΔG°), there were subtle yet important differences in some of thermodynamic properties (ΔH°, ΔS°) associated with each of the conformational equilibria. These differences prompted us to propose a model for cADPR in which the interactions between the A2′-N3, A5″-N3, and H2-R5′ atoms serve to fine-tune the N-glycosidic torsion angles (χ).

Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: A C2′ endo/syn "southern" ribose conformation underlies activity at the sea urchin cADPR receptor

Novel 8-substituted base and sugar-modified analogues of the Ca 2+ mobilizing second messenger cyclic adenosine 5′-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by 1H NMR spectroscopy revealed that a C2′ endo/syn conformation of the "southern" ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor.