2-Ethynyl Adenosine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 551030

CAS#: 99044-57-2

Description: 2-Ethynyl Adenosine is an adenosine derivative, used to capture newly polyadenylated transcripts. 2-Ethynyl Adenosine is also used as a non-radioactive chemical reporter for protein AMPylation.


Price and Availability

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2-Ethynyl Adenosine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 551030
Name: 2-Ethynyl Adenosine
CAS#: 99044-57-2
Chemical Formula: C12H13N5O4
Exact Mass: 291.0968
Molecular Weight: 291.267
Elemental Analysis: C, 49.48; H, 4.50; N, 24.04; O, 21.97


Synonym: 2-Ethynyl Adenosine; 2 Ethynyl Adenosine; 2-Ethynyl-Adenosine; 2-Ethynyl-Ade

IUPAC/Chemical Name: (2R,3R,4S,5R)-2-(6-Amino-2-ethynylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

InChi Key: ILZDIASZHUIPSA-JJNLEZRASA-N

InChi Code: InChI=1S/C12H13N5O4/c1-2-6-15-10(13)7-11(16-6)17(4-14-7)12-9(20)8(19)5(3-18)21-12/h1,4-5,8-9,12,18-20H,3H2,(H2,13,15,16)/t5-,8-,9-,12-/m1/s1

SMILES Code: O[C@H]1[C@H](N2C=NC3=C(N)N=C(C#C)N=C23)O[C@H](CO)[C@H]1O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Creech C, Kanaujia M, Causey CP. Synthesis and evaluation of 2-ethynyl-adenosine-5'-triphosphate as a chemical reporter for protein AMPylation. Org Biomol Chem. 2015 Aug 21;13(31):8550-5. doi: 10.1039/c5ob01081k. PubMed PMID: 26173047.

2: Tosh DK, Deflorian F, Phan K, Gao ZG, Wan TC, Gizewski E, Auchampach JA, Jacobson KA. Structure-guided design of A(3) adenosine receptor-selective nucleosides: combination of 2-arylethynyl and bicyclo[3.1.0]hexane substitutions. J Med Chem. 2012 May 24;55(10):4847-60. doi: 10.1021/jm300396n. Epub 2012 May 16. PubMed PMID: 22559880; PubMed Central PMCID: PMC3371665.

3: Mathieu R, Baurand A, Schmitt M, Gachet C, Bourguignon JJ. Synthesis and biological activity of 2-alkylated deoxyadenosine bisphosphate derivatives as P2Y(1) receptor antagonists. Bioorg Med Chem. 2004 Apr 1;12(7):1769-79. PubMed PMID: 15028267.