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Synthesis of 21,31,51-trideoxyuridine-51-methylphosphonic acid and its diphosphate derivative. Study of the interaction with HIV-1reverse transcriptase

MPG-Autoren
http://pubman.mpdl.mpg.de/cone/persons/resource/persons94973

Rittinger,  Katrin
Emeritus Group Biophysics, Max Planck Institute for Medical Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons196902

Divita,  Gilles
Emeritus Group Biophysics, Max Planck Institute for Medical Research, Max Planck Society;

http://pubman.mpdl.mpg.de/cone/persons/resource/persons93142

Goody,  R.S
Emeritus Group Biophysics, Max Planck Institute for Medical Research, Max Planck Society;

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Zitation

Benzaria, S., Maury, G., Gosselin, G., Rittinger, K., Divita, G., Goody, R., et al. (1994). Synthesis of 21,31,51-trideoxyuridine-51-methylphosphonic acid and its diphosphate derivative. Study of the interaction with HIV-1reverse transcriptase. Antiviral Chemistry & Chemotherapy, 5(4), 221-228. doi:10.1177/095632029400500403.


Zitierlink: http://hdl.handle.net/11858/00-001M-0000-002A-F1D5-5
Zusammenfassung
2′,3′,5′-Trideoxyuridine-5′-methylphosphonate, [8], was synthesized from ddU. The 5′,6′ carbon-carbon bond was formed by condensing the 5′-aldehyde of ddU and a Wittig reagent. The binding interaction of the diphosphate derivative [10] of the phosphonate [8] with HIV-1 reverse transcriptase (RT) was studied using methods based primarily on fluorescence spectroscopy. From the quenching of intrinsic tryptophan fluorescence of RT during its titration against [10], a dissociation constant of 24 μm was calculated at 25°C. In the presence of a DNA/DNA template/primer of defined sequence and RT, [10] and a fluorescent derivative of ddTTP competed for binding to RT without incorporation of ddU-5′-methylphosphonate. In the presence of a 0.5 mm concentration of [10], the RT activity measured with Poly(rA)/(dT)15 and [3H] dTTP was lowered to 65%. All our observations are consistent with suppression of the catalysis of bond formation between the OH at the primer 3′-end and α-P of [10] after formation of the complex between RT, template/primer and [10].