Cas no 31966-52-6 (8-Azidoadenosine 3':5'-Cyclic Monophosphate)
8-Azidoadenosine 3':5'-Cyclic Monophosphate Chemical and Physical Properties
Names and Identifiers
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- Adenosine, 8-azido-,cyclic 3',5'-(hydrogen phosphate) (8CI,9CI)
- 8-AZIDOADENOSINE 3':5'-CYCLIC MONOPHOSPHATE
- 8-AZIDOADENOSINE-3'5'-CYCLIC -MONOPHOSPHATE
- 8-Azidoadenosine 3',5'-cyclic monophosphosphate free acid
- 8-AZIDOADENOSINE 3':5'-CYCLICMONOPHOSPHA TE FREE AC
- 8-AZIDOADENOSINE-3',5'-CYCLIC MONOPHOSPHATE SODIUM SALT
- 8-N3-CAMP SODIUM SALT
- CHEMBL3272800
- 6-(6-Amino-8-azido-9H-purin-9-yl)-2,7-dihydroxytetrahydro-2H,4H-2lambda~5~-furo[3,2-d][1,3,2]dioxaphosphinin-2-one
- 8-Azido-cAMP
- 8-Azidoadenosine 3',5'-monophosphate
- 8-N3-cAMP
- 8-Azidoadenosine-3',5'-monophosphate
- HY-134321
- (4aR,6R,7R,7aS)-6-(6-amino-8-azidopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
- 8-Azidoadenosine cyclic 3',5'-(hydrogen phosphate)
- DTXSID70953852
- 31966-52-6
- 8-AZIDOADENOSINE-3',5'-cyclic-MONOPHOSPHATE
- MFCD00057127
- SCHEMBL14167816
- Adenosine, 8-azido-, cyclic 3',5'-(hydrogen phosphate)
- 8-Azido-cyclic AMP
- DA-49999
- 8-Azidoadenosine 3':5'-Cyclic Monophosphate
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- Inchi： 1S/C10H11N8O6P/c11-7-4-8(14-2-13-7)18(10(15-4)16-17-12)9-5(19)6-3(23-9)1-22-25(20,21)24-6/h2-3,5-6,9,19H,1H2,(H,20,21)(H2,11,13,14)/t3-,5-,6-,9-/m1/s1
- InChI Key： KTMLKBFMGWQTEK-UUOKFMHZSA-N
- SMILES： P1(=O)(O)OC[C@@H]2[C@H]([C@H]([C@H](N3C(N=[N+]=[N-])=NC4C(N)=NC=NC3=4)O2)O)O1
Computed Properties
- Exact Mass: 370.05400
- Monoisotopic Mass: 370.05391710g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 3
- Hydrogen Bond Acceptor Count: 12
- Heavy Atom Count: 25
- Rotatable Bond Count: 2
- Complexity: 635
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 4
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 1
- XLogP3: -1.3
- Topological Polar Surface Area: 169?2
Experimental Properties
- PSA: 214.40000
- LogP: 0.15836
8-Azidoadenosine 3':5'-Cyclic Monophosphate Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| TRC | A822003-1mg |
8-Azidoadenosine 3':5'-Cyclic Monophosphate |
31966-52-6 | 1mg |
$ 230.00 | 2023-04-19 | ||
| TRC | A822003-2.5mg |
8-Azidoadenosine 3':5'-Cyclic Monophosphate |
31966-52-6 | 2.5mg |
$ 448.00 | 2023-04-19 | ||
| TRC | A822003-10mg |
8-Azidoadenosine 3':5'-Cyclic Monophosphate |
31966-52-6 | 10mg |
$ 661.00 | 2023-04-19 | ||
| SHENG KE LU SI SHENG WU JI SHU | sc-221123-1mg |
8-Azidoadenosine 3':5'-cyclic monophosphate, |
31966-52-6 | ≥95% | 1mg |
￥1579.00 | 2023-09-05 | |
| SHENG KE LU SI SHENG WU JI SHU | sc-221123-1 mg |
8-Azidoadenosine 3':5'-cyclic monophosphate, |
31966-52-6 | ≥95% | 1mg |
￥1,579.00 | 2023-07-11 |
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8-Azidoadenosine 3':5'-Cyclic Monophosphate Related Literature
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Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
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Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
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Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu Yan RSC Adv., 2013,3, 14960-14962
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A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569
Related Categories
- Solvents and Organic Chemicals Organic Compounds Nucleosides, nucleotides, and analogues Purine nucleotides 3',5'-cyclic purine nucleotides
- Solvents and Organic Chemicals Organic Compounds Nucleosides, nucleotides, and analogues Purine nucleotides Cyclic purine nucleotides 3',5'-cyclic purine nucleotides
Additional information on 8-Azidoadenosine 3':5'-Cyclic Monophosphate
8-Azidoadenosine 3':5'-Cyclic Monophosphate: A Comprehensive Overview
8-Azidoadenosine 3':5'-Cyclic Monophosphate (CAS No. 31966-52-6) is a unique nucleotide analog that has garnered significant attention in the fields of biochemistry, pharmacology, and molecular biology. This compound is a derivative of adenosine monophosphate (AMP), with a key structural modification involving the introduction of an azide group at the 8-position of the adenine ring. This modification imparts distinct chemical and biological properties to the molecule, making it a valuable tool in various research and therapeutic applications.
The azide group in 8-Azidoadenosine 3':5'-Cyclic Monophosphate plays a pivotal role in its functionality. Azides are known for their ability to undergo click chemistry reactions, particularly the Huisgen cycloaddition reaction, which enables the formation of stable triazole linkages. This property has made 8-Azidoadenosine 3':5'-Cyclic Monophosphate a valuable substrate for bioconjugation studies, allowing researchers to attach various molecules, such as fluorophores, enzymes, or other biomolecules, to the adenine ring with high precision. Such conjugates are widely used in imaging studies, drug delivery systems, and biosensor development.
Recent advancements in click chemistry have further expanded the utility of 8-Azidoadenosine 3':5'-Cyclic Monophosphate. For instance, its use in click-to-release systems has enabled the controlled delivery of bioactive molecules in response to specific stimuli. This innovation holds promise for targeted drug delivery and personalized medicine, where precise control over drug release is critical. Additionally, the compound's ability to participate in inverse electron-demand Diels-Alder reactions has opened new avenues for creating complex biomolecular architectures.
In the realm of molecular biology, 8-Azidoadenosine 3':5'-Cyclic Monophosphate has been employed as a probe for studying nucleotide metabolism and signaling pathways. Its structural similarity to natural nucleotides allows it to be incorporated into biological systems without significantly disrupting normal cellular processes. This feature makes it an ideal tool for investigating the role of adenosine signaling in various physiological and pathological conditions.
One of the most exciting developments involving 8-Azidoadenosine 3':5'-Cyclic Monophosphate is its application in CRISPR-Cas9 genome editing systems. Researchers have utilized its azide functionality to create clickable guides for Cas9 proteins, enabling precise targeting and editing of specific genomic loci. This approach has significantly enhanced the efficiency and specificity of CRISPR-based editing, paving the way for novel therapeutic strategies in genetic disorders.
Moreover, 8-Azidoadenosine 3':5'-Cyclic Monophosphate has found applications in drug discovery efforts targeting adenosine receptors. These receptors are involved in numerous physiological processes, including neurotransmission, immune regulation, and cardiovascular function. By designing azide-containing analogs that selectively bind to adenosine receptors, researchers can develop potential leads for treating conditions such as asthma, inflammation, and cardiovascular diseases.
The synthesis of 8-Azidoadenosine 3':5'-Cyclic Monophosphate typically involves multi-step chemical transformations starting from adenosine or its derivatives. The introduction of the azide group is often achieved through nucleophilic substitution or coupling reactions under mild conditions to preserve the integrity of the nucleotide structure. The resulting compound is then purified using chromatographic techniques to ensure high purity levels required for biological studies.
In terms of stability and storage, 8-Azidoadenosine 3':5'-Cyclic Monophosphate should be handled with care due to its sensitivity to light and oxidative conditions. Proper storage under inert atmospheres or at low temperatures is essential to maintain its chemical integrity and biological activity.
Looking ahead, ongoing research continues to uncover new applications for 8-Azidoadenosine 3':5'-Cyclic Monophosphate across diverse scientific disciplines. Its unique combination of chemical reactivity and biological compatibility positions it as a versatile tool for advancing our understanding of molecular mechanisms and developing innovative therapeutic interventions.
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