Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.1.26.13 extracted from

  • Yanagita, H.; Urano, E.; Matsumoto, K.; Ichikawa, R.; Takaesu, Y.; Ogata, M.; Murakami, T.; Wu, H.; Chiba, J.; Komano, J.; Hoshino, T.
    Structural and biochemical study on the inhibitory activity of derivatives of 5-nitro-furan-2-carboxylic acid for RNase H function of HIV-1 reverse transcriptase (2011), Bioorg. Med. Chem., 19, 816-825.
    View publication on PubMed
Search for more literature for 3.1.26.13

Application

Application Comment Organism
drug development RNase H activity is an attractive target for a new class of antiviral drugs Human immunodeficiency virus 1

Cloned(Commentary)

Cloned (Comment) Organism
cloning a His-tagged p66 or p51 HIV-1 RT DNA fragment into the pQE-9 vector and expression in Escherichia coli strain BL21(DE3)pLys Human immunodeficiency virus 1

Protein Variants

Protein Variants Comment Organism
C280S site-directed mutagenesis Human immunodeficiency virus 1
F160S site-directed mutagenesis Human immunodeficiency virus 1

Inhibitors

Inhibitors Comment Organism Structure
2-(2,3-dihydro-1H-inden-1-ylamino)-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-(2,3-dihydro-1H-inden-2-ylamino)-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-(tert-butylamino)-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-amino-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-oxo-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)ethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-oxo-2-(propan-2-yloxy)ethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-oxo-2-(tetrahydrofuran-2-ylamino)ethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-oxo-2-[(2-phenylpropan-2-yl)amino]ethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[(2-methyl-1-phenylpropan-2-yl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[(2-methylbutan-2-yl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[(4-hydroxybenzyl)(tetrahydrofuran-2-ylmethyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[benzyl(tetrahydrofuran-2-ylmethyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(2-phenylethyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(3-nitrobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(3-oxo-3-phenylpropyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(3-phenylpropyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(4-fluorobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(4-methoxybenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(4-nitrobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(pentafluorobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl(phenyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl[2-(trifluoromethyl)benzyl]amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl[3-(trifluoromethyl)benzyl]amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[tert-butyl[4-(trifluoromethyl)benzyl]amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[[2-(acetyloxy)benzyl](tert-butyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[[4-(acetyloxy)benzyl](tert-butyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
2-[[4-(benzyloxy)benzyl](tert-butyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
3,3-dimethyl-2-oxobutyl 5-nitrofuran-2-carboxylate
-
 Human immunodeficiency virus 1
additional information design, synthesis, and screening of derivatives of 5-nitro-furan-2-carboxylic acid as inhibitors of the RNAse H activity of HIV-1 reverse transcriptase, overview. Modulation of the 5-nitro-furan-2-carboxylic moiety results in a drastic decrease in inhibitory potency. Binding mode of active derivatives, in which three oxygen atoms aligned in a straight form at the nitro-furan moiety are coordinated to two divalent metal ions located at RNase H reaction site. The nitro-furan-carboxylic moiety is one of the critical scaffolds for RNase H inhibition. Cytotoxicity of the synthesized compounds, overview Human immunodeficiency virus 1

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Human immunodeficiency virus 1 HIV-1 reverse transcriptase has two enzymatic functions, DNA polymerase and RNase H activities ?
-
 ?

Organism

Organism UniProt Comment Textmining
Human immunodeficiency virus 1
-
 HIV-1
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged p66 or p51 HIV-1 RT DNA fragment from Escherichia coli strain BL21(DE3)pLys by nickel affinity chromatography, expression of a heterodimer of wild-type or F160S and C280S mutant p66 and p51 using plasmid vector RT69A in Escherichia coli strain Rosetta Human immunodeficiency virus 1

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information HIV-1 reverse transcriptase has two enzymatic functions, DNA polymerase and RNase H activities Human immunodeficiency virus 1 ?
-
 ?

Synonyms

Synonyms Comment Organism
RNase H
-
 Human immunodeficiency virus 1

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Human immunodeficiency virus 1

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
 assay at Human immunodeficiency virus 1

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0009
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(phenyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0042
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-oxo-2-(tetrahydrofuran-2-ylamino)ethyl 5-nitrofuran-2-carboxylate
0.0043
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[(2-methyl-1-phenylpropan-2-yl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0043
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-oxo-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)ethyl 5-nitrofuran-2-carboxylate
0.005
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[(4-hydroxybenzyl)(tetrahydrofuran-2-ylmethyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0055
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-(2,3-dihydro-1H-inden-2-ylamino)-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0058
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[(2-methylbutan-2-yl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0061
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-(2,3-dihydro-1H-inden-1-ylamino)-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0068
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(pentafluorobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0069
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(4-nitrobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0071
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-amino-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0075
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(4-methoxybenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0077
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[benzyl(tetrahydrofuran-2-ylmethyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.008
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl[4-(trifluoromethyl)benzyl]amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0082
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-oxo-2-[(2-phenylpropan-2-yl)amino]ethyl 5-nitrofuran-2-carboxylate
0.0085
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(4-fluorobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0085
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl[3-(trifluoromethyl)benzyl]amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0087
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[[4-(acetyloxy)benzyl](tert-butyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.009
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl[2-(trifluoromethyl)benzyl]amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0098
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(3-nitrobenzyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0128
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[[2-(acetyloxy)benzyl](tert-butyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0132
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-oxo-2-(propan-2-yloxy)ethyl 5-nitrofuran-2-carboxylate
0.0142
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(2-phenylethyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.018
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-(tert-butylamino)-2-oxoethyl 5-nitrofuran-2-carboxylate
0.0219
-
 pH 7.5, 37°C Human immunodeficiency virus 1 3,3-dimethyl-2-oxobutyl 5-nitrofuran-2-carboxylate
0.05
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(3-phenylpropyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.05
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[tert-butyl(3-oxo-3-phenylpropyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate
0.05
-
 pH 7.5, 37°C Human immunodeficiency virus 1 2-[[4-(benzyloxy)benzyl](tert-butyl)amino]-2-oxoethyl 5-nitrofuran-2-carboxylate