Cas no 59587-07-4 (2-Azido Adenosine)

2-Azido Adenosine is a modified nucleoside derivative where an azido group is introduced at the 2-position of the adenosine scaffold. This functionalization imparts unique reactivity, making it a valuable intermediate in bioorthogonal chemistry, particularly for click chemistry applications such as Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The azido group enables selective conjugation with alkynes, facilitating the labeling or crosslinking of biomolecules. Its structural similarity to adenosine allows for incorporation into nucleic acid probes or metabolic studies. The compound is particularly useful in chemical biology for investigating nucleotide-protein interactions or designing targeted therapeutics. Careful handling is advised due to the potential instability of the azido moiety under certain conditions.
2-Azido Adenosine structure
2-Azido Adenosine structure
Product Name:2-Azido Adenosine
CAS No:59587-07-4
MF:C10H12N8O4
MW:308.253479957581
CID:377481
PubChem ID:510978
Update Time:2025-05-19

2-Azido Adenosine Chemical and Physical Properties

Names and Identifiers

    • Adenosine, 2-azido-
    • 2-Azido Adenosine
    • (2R,3R,4S,5R)-2-(6-amino-2-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    • 2-Azido-adenosin
    • 2-Azido-adenosine
    • 2-Azido-D-adenosine
    • Adenosine,2-azido
    • NSC 36905;
    • AKOS030240741
    • 2-(6-amino-2-azidopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
    • (2R,3R,4S,5R)-2-(6-amino-2-azido-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
    • NSC 36905
    • SCHEMBL16781783
    • DTXSID60208247
    • 59587-07-4
    • (4S,2R,3R,5R)-2-[6-Amino-2-(diazoazamvinyl)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
    • 2-Azidoadenosine
    • Inchi: 1S/C10H12N8O4/c11-7-4-8(15-10(14-7)16-17-12)18(2-13-4)9-6(21)5(20)3(1-19)22-9/h2-3,5-6,9,19-21H,1H2,(H2,11,14,15)/t3-,5-,6-,9-/m1/s1
    • InChI Key: BSZZPOARGMTJKQ-UUOKFMHZSA-N
    • SMILES: O1[C@H](CO)[C@H]([C@H]([C@@H]1N1C=NC2C(N)=NC(N=[N+]=[N-])=NC1=2)O)O

Computed Properties

  • Exact Mass: 308.09800
  • Monoisotopic Mass: 308.098151
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 22
  • Rotatable Bond Count: 3
  • Complexity: 462
  • 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: 0.2
  • Topological Polar Surface Area: 154

Experimental Properties

  • Color/Form: Gray white to gray solid
  • Melting Point: 170-172°C
  • Solubility: DMSO (Slightly), Methanol (Very Slightly)
  • PSA: 189.29000
  • LogP: -1.00424

2-Azido Adenosine Security Information

  • Storage Condition:-20°C Freezer

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2-Azido Adenosine Suppliers

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(CAS:59587-07-4)2-AzidoAdenosine
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Quantity:10g
Purity:97%
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Additional information on 2-Azido Adenosine

Introduction to 2-Azido Adenosine (CAS No: 59587-07-4)

2-Azido Adenosine, with the chemical identifier CAS No: 59587-07-4, is a specialized nucleoside derivative that has garnered significant attention in the field of biochemical research and pharmaceutical development. This compound belongs to the adenosine family, characterized by the presence of an azido functional group at the 2-position of the ribose sugar. The azido group introduces unique reactivity, making 2-Azido Adenosine a valuable tool in synthetic biology and medicinal chemistry.

The structure of 2-Azido Adenosine consists of a purine base (adenine) linked to a ribose sugar, with the azido (-N?) substituent attached to the 2' carbon atom. This modification imparts distinct chemical properties, enabling its use in various biochemical transformations. The compound's reactivity is primarily due to the electron-withdrawing nature of the azido group, which facilitates nucleophilic substitution reactions. These properties have been leveraged in the development of novel therapeutic agents and in studying enzyme mechanisms involving nucleoside metabolism.

In recent years, 2-Azido Adenosine has been explored as a key intermediate in the synthesis of modified nucleosides with potential therapeutic applications. For instance, researchers have utilized this compound to develop analogs that exhibit enhanced stability or altered biological activity compared to natural adenosine derivatives. Such modifications are crucial for creating drugs with improved pharmacokinetic profiles or targeted mechanisms of action.

One notable area of research involving 2-Azido Adenosine is its role in modulating adenosine receptor signaling. Adenosine receptors (A?, A?A, A?B, and A?) are G-protein coupled receptors (GPCRs) that play critical roles in various physiological processes, including neurotransmission, inflammation, and cardiovascular function. By synthesizing derivatives of 2-Azido Adenosine, scientists aim to develop selective agonists or antagonists that can modulate these receptors for therapeutic benefit. For example, A?A receptor agonists have shown promise in treating neurological disorders such as Parkinson's disease and stroke.

Moreover, 2-Azido Adenosine has been employed in studies focused on enzymatic degradation pathways. The azido group can serve as a handle for probing enzymatic activity by undergoing specific chemical reactions upon cleavage. This approach has been instrumental in understanding how enzymes like adenosine deaminase or nucleoside kinases interact with nucleoside substrates. Such insights are vital for designing inhibitors or activators that can regulate metabolic pathways relevant to diseases like cancer or genetic disorders.

Recent advancements in click chemistry have also highlighted the utility of 2-Azido Adenosine. The azido group is highly compatible with copper-catalyzed azide-alkyne cycloaddition (CuAAC), a widely used method for constructing biaryl compounds or conjugating biomolecules. Researchers have utilized this property to create novel nucleoside-based probes for imaging applications or to link adenosine derivatives with other bioactive molecules. These innovations underscore the versatility of 2-Azido Adenosine as a building block in synthetic biology.

The pharmaceutical industry has taken notice of 2-Azido Adenosine due to its potential as a scaffold for drug discovery. By leveraging its unique reactivity, chemists can generate libraries of modified nucleosides for high-throughput screening against disease targets. Several preclinical studies have demonstrated the efficacy of 2-Azido Adenosine-derived compounds in models of inflammation, neurodegeneration, and metabolic disorders. These findings position CAS No: 59587-07-4 as a promising candidate for further development into clinical therapies.

In conclusion, 2-Azido Adenosine represents a fascinating compound with broad applications in biochemical research and drug development. Its structural features and reactivity make it an invaluable tool for synthetic chemists and biologists alike. As research continues to uncover new ways to utilize this derivative, its significance in advancing therapeutic strategies is likely to grow further. The ongoing exploration of CAS No: 59587-07-4 underscores its potential as a cornerstone in future medical innovations.

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(CAS:59587-07-4)2-AzidoAdenosine
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Purity:97%
Quantity:10g
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