2-Ethynyl Adenosine

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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.


Chemical Structure

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2-Ethynyl Adenosine
CAS# 99044-57-2

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

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 291.267 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.