3'‐Fluoro‐2',3'‐dideoxyribonucleoside 5'‐triphosphates: terminators of DNA synthesis

Chidgeavadze, Zurab G.; Scamrov, Andrei V.; Beabealashvilli, Robert Sh.; Kvasyuk, Е. I.; Зайцева, Г. С.; Mikhailopulo, Igor A.; Kowollik, G.; Langen, P.

doi:10.1016/0014-5793(85)80792-4

Cited by 24 publications

(15 citation statements)

References 10 publications

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“…The data in Fig. 3 natural bases (2,16,18,27), were confirmed here for a series of deoxycytidine derivatives modified in the base moiety and/or in the sugar moiety (Table 1). However, NH2Met dCTP and N3MetdCTP had no inhibitory effects on either cellular DNA polymerase, so N3MetdCTP displayed the highest selectivity of all the tested compounds.…”

supporting

confidence: 74%

Comparative inhibition of hepatitis B virus DNA polymerase and cellular DNA polymerases by triphosphates of sugar-modified 5-methyldeoxycytidines and of other nucleoside analogs

Matthes

Reimer

Janta-Lipinski

et al. 1991

Antimicrob Agents Chemother

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Of a series of 14 nucleoside 5'-triphosphates, those of 2',3'-dideoxy-3'-fluoro-5-methylcytidine, 3'-azido-2',3'-dideoxy-5-methylcytidine, 2',3'-dideoxy-3'-fluoroguanosine, 2',3'-didehydro-2',3'-dideoxy-5-methylcytidine, 2',3'-dideoxy-3'-fluoro-5-ethylcytidine, and 2',3'-dideoxy-3'-fluoroadenosine emerged as the most potent inhibitors of hepatitis B virus DNA polymerase (50% inhibitory dose, 0.03 to 0.35 microM). In contrast, cellular DNA polymerases proved to be resistant to (alpha) or partially affected by (beta) these analogs. These compounds are among the most effective and selective inhibitors of endogenous hepatitis B virus DNA polymerase recognized to date.

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supporting

confidence: 74%

Comparative inhibition of hepatitis B virus DNA polymerase and cellular DNA polymerases by triphosphates of sugar-modified 5-methyldeoxycytidines and of other nucleoside analogs

Matthes

Reimer

Janta-Lipinski

et al. 1991

Antimicrob Agents Chemother

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“…The chemical structures of compounds [1] - [8] are shown in Figure 2. Compounds [1]- [4], [6], [8] were prepared according to the general scheme: The 5'-hydroxyl was protected with a tert-butyldiphenylsilyl (TBDPS) group, and the specific addition of the 3'-protecting Figure 2. Chemical structures of the 3'-modified-nucleotides.…”

Section: Organic Synthesesmentioning

confidence: 99%

“…2 '-Deoxy-3 '-O-tetrahydropyranyladenosine [4]. 2'-Deoxy-5'-tertbutyldiphenylsilyladenosine [9] (2.90 g, 5.92 mmol), dihydropyran (4.89 g, 59.2 mmol, 10 equiv.)…”

Section: Organic Synthesesmentioning

confidence: 99%

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Termination of DNA synthesis by novel 3'-modifieddeoxyribonucleoside 5'-triphosphates

Metzker¹,

Raghavachari

Richards³

et al. 1994

Nucl Acids Res

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Eight 3'-modified-dNTPs were synthesized and tested in two different DNA template assays for incorporation activity. From this enzymatic screen, two 3'-O-methyl-dNTPs were shown to terminate DNA syntheses mediated by a number of polymerases and may be used as alternative terminators in Sanger sequencing. 3'-O-(2-Nitrobenzyl)-dATP is a UV sensitive nucleotide and was shown to be incorporated by several thermostable DNA polymerases. Base specific termination and efficient photolytic removal of the 3'-protecting group was demonstrated. Following deprotection, DNA synthesis was reinitiated by the incorporation of natural nucleotides into DNA. The identification of this labile terminator and the demonstration of a one cycle stop-start DNA synthesis are initial steps in the development of a novel sequencing strategy.

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“…track 6). In the case of DNA polymerase I KF, the effect of dddTTP was compared with that of dTTP(3'-F) [11]; dTTP(3'-F) is known to be one of the strongest termination substrates for the system with DNA polymerase I KF [12]. From tracks 12 and 14,15 it FEBS is clear that both compounds terminate DNA synthesis but the effect of dddTTP is stronger.…”

Section: Data Polymerase I Kf From E Coli Amvmentioning

confidence: 99%

Properties of 2′,3′‐dideoxy‐2′,3′‐dehydrothymidine 5′‐triphosphate in terminating DNA synthesis catalyzed by several different DNA polymerases

Dyatkina¹,

Minassian²,

Kukhanova³

et al. 1987

FEBS Letters

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-dehydrothymidine 5'-triphosphate (dddTTP) shows termination substrate properties in the DNA synthesis catalyzed by E. coli DNA polymerase I KF, rat liver DNA polymerase r, reverse transcriptases of avian myeloblastosis virus and Raus sarcoma virus and calf thymus terminal deoxynucleotidyl transferase. This implies that the mononucleotide residue of dddTTP incorporates into 3'-termini of newly synthesized DNA chains. However, dddTTP has no influence on the DNA synthesis catalyzed by calf thymus DNA polymerase ct. In the case of some DNA polymerases dddTTP was one order of magnitude more effective in comparison with the other known termination substrates.

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3'‐Fluoro‐2',3'‐dideoxyribonucleoside 5'‐triphosphates: terminators of DNA synthesis

Cited by 24 publications

References 10 publications

Comparative inhibition of hepatitis B virus DNA polymerase and cellular DNA polymerases by triphosphates of sugar-modified 5-methyldeoxycytidines and of other nucleoside analogs

Comparative inhibition of hepatitis B virus DNA polymerase and cellular DNA polymerases by triphosphates of sugar-modified 5-methyldeoxycytidines and of other nucleoside analogs

Termination of DNA synthesis by novel 3'-modifieddeoxyribonucleoside 5'-triphosphates

Properties of 2′,3′‐dideoxy‐2′,3′‐dehydrothymidine 5′‐triphosphate in terminating DNA synthesis catalyzed by several different DNA polymerases

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