InChI key
MPXDAIBTYWGBSL-UHFFFAOYSA-N
InChI
1S/C7H6F2/c1-5-2-3-6(8)4-7(5)9/h2-4H,1H3
SMILES string
Cc1ccc(F)cc1F
assay
99%
form
liquid
refractive index
n20/D 1.449 (lit.)
bp
113-117 °C (lit.)
density
1.12 g/mL at 25 °C (lit.)
General description
2,4-Difluorotoluene was synthesized as a nucleotide analog and was incorporated into DNA and undergoes replication by DNA polymerase enzymes.
Application
2,4-Difluorotoluene was used in the synthesis of new hydrophobic isosteres of pyrimidines and purine nucleosides.
K M Guckian et al.
Nature structural biology, 5(11), 954-959 (1998-11-10)
A nonpolar aromatic nucleoside derivative based on 2,4-difluorotoluene (F), a non-hydrogen bonding shape analog of thymidine, was recently shown to be replicated against adenine with high efficiency and fidelity. This led to the suggestion that geometric matching, potentially even in
M Meyer et al.
Journal of biomolecular structure & dynamics, 15(3), 619-624 (1998-01-24)
Recent experiments have shown that difluorotoluene (F), a nonpolar isostere for thymine (T), codes efficiently and specifically for adenine (A) in DNA replication. F has almost the same shape as thymine but it is unable to form conventional hydrogen bonds
Wenonah A Vercoutere et al.
Nucleic acids research, 31(4), 1311-1318 (2003-02-13)
Nanoscale alpha-hemolysin pores can be used to analyze individual DNA or RNA molecules. Serial examination of hundreds to thousands of molecules per minute is possible using ionic current impedance as the measured property. In a recent report, we showed that
D Liu et al.
Chemistry & biology, 4(12), 919-926 (1998-03-07)
The nonpolar nucleoside of difluorotoluene (F) was previously found to behave similarly to thymidine in single-site deoxynucleoside triphosphate (dNTP) insertion experiments with the Klenow fragment (KF) of DNA polymerase I. Further study was needed, first to see whether F-A base
Shuangluo Xia et al.
Journal of the American Chemical Society, 133(26), 10003-10005 (2011-06-15)
Results obtained using 2,4-difluorotoluene nucleobase (dF) as a nonpolar thymine isostere by Kool and colleagues challenged the Watson-Crick dogma that hydrogen bonds between complementary bases are an absolute requirement for accurate DNA replication. Here, we report crystal structure of an
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