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N3289 Sigma-Aldrich

N2-Ethyl-2′-deoxyguanosine

≥98% (HPLC), solid

Synonym: N2-Et-dG

  • CAS Number 101803-03-6

  • Empirical Formula (Hill Notation) C12H17N5O4

  • Molecular Weight 295.29

  •  MDL number MFCD01631004

  •  PubChem Substance ID 329818605

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, DNA-RNA Transcription Regulators,
Quality Level   100
assay   ≥98% (HPLC)
form   solid
color   white to off-white
solubility   H2O: >5 mg/mL
storage temp.   2-8°C
SMILES string   CCNC1=Nc2c(ncn2[C@H]3C[C@H](O)[C@@H](CO)O3)C(=O)N1
InChI   1S/C12H17N5O4/c1-2-13-12-15-10-9(11(20)16-12)14-5-17(10)8-3-6(19)7(4-18)21-8/h5-8,18-19H,2-4H2,1H3,(H2,13,15,16,20)/t6-,7+,8+/m0/s1
InChI key   VOKQFDULHQUWAV-XLPZGREQSA-N

Description

General description

N2-Et-dG, an adduct between DNA and the first metabolite of ethanol (acetaldehyde), strongly blocks transcription by RNA polymerases (RNAPs), including mammalian RNAPII and yeast RNAPII, E. coli RNAP, as well as T7 RNAP. All three of the multisubunit RNAPs incorporate a single rNTP residue opposite the N2-Et-dG lesion. The mammalian RNAPII exclusively incorporates cytidine monophosphate (CMP) opposite the N2-Et-dG lesion. The accessory transcription factor TFIIS does not usually act as a lesion bypass factor; instead, it stimulates the polymerase to remove the CMP incorporated opposite the lesion by mammalian RNAPII. N2-Et-dG reduces CTP incorporation by ~1500 fold.

Packaging

5, 25 mg in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGI
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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