2-Ethynyl Adenosine

• CAT Number: I012887
• CAS Number: 99044-57-2
• Molecular Formula: C12H13N5O4
• Molecular Weight: 291.267
• Purity: 95%
• Storage: -20 °C
• Analysis method: HPLC
• IUPAC Name: (2R,3R,4S,5R)-2-(6-amino-2-ethynylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• InChI: 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
• InChIKey: ILZDIASZHUIPSA-JJNLEZRASA-N
• SMILES: C#CC1=NC2=C(C(=N1)N)N=CN2C3C(C(C(O3)CO)O)O

2-Ethynyl-labeled adenosine (2-EA) can be used to measure de novo mRNA poly(A) tail synthesis in proliferating cells. 2-EA is cell permeable and incorporates into nascent mRNA transcripts both transcriptionally by RNA polymerase I,II and III and posttranscriptionally by poly(A) polymerase instead of their natural analolg adenosine.
The resulting ethynyl-functionalized RNA can subsequently be detected via Cu(I)-catalyzed click chemistry that offers the choice to introduce a Biotin group (via Azides of Biotin) for subsequent purification tasks or a fluorescent group (via Azides of fluorescent dyes) for subsequent microscopic imaging.