(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Electric Literature of C13H18O9) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.
Electric Literature of C13H18O9《β-L-Thymidine 5′-triphosphate analogs as DNA polymerase substrates》 was published in 1992. The authors were Van Draanen, Nanine A.;Tucker, S. Craig;Boyd, F. Leslie;Trotter, B. Wesley;Reardon, John E., and the article was included in《Journal of Biological Chemistry》. The author mentioned the following in the article:
β-L-3′-Deoxythymidine 5′-triphosphate (L-ddTTP) and β-L-3′-deoxy-2′,3′-didehydrothymidine 5′-triphosphate (L-d4TTP) were substrates for human immunodeficiency virus (HIV) reverse transcriptase, Escherichia coli DNA polymerase I (Klenow), and Sequenase (modified T7 DNA polymerase). The β-D– and β-L-enantiomers of 5-methyluridine 5′-triphosphate (rTTP) were inhibitors but not substrates of reverse transcriptase. The steady-state Km values for L-ddTTP and L-d4TTP, with all three enzymes, were 12-70-fold larger than the Km values for the corresponding D-enantiomers. The Km value of reverse transcriptase for L-ddTTP was 50-fold larger than that for D-ddTTP because the Kd for L-ddTTP was 5-fold larger than that for D-ddTTP, and the first-order rate constant for incorporation of L-ddTMP into the template-primer was 10% that of the D-enantiomer. The D– and L-enantiomers had kcat values with reverse transcriptase and Sequenase that were similar to kcat for the natural substrate, thymidine 5′-triphosphate (dTTP). Thus, the rate determining step appeared to be dissociation of the enzyme-chain-terminated template-primer complex. In contrast, kcat values for the L-enantiomers with Klenow were only 0.1% that of dTTP, and the kcat values for the D-enantiomers were 15% the kcat for dTTP. The reduced kcat values were due to a change in rate-determining step from dissociation of the Klenow-chain-terminated template-primer complex to an earlier step in the reaction mechanism, presumably catalysis. Thus, these DNA polymerases did not stereospecifically recognize D-nucleoside 5′-triphosphate analogs as substrates. The virucidal activity of some nucleoside analogs against HIV is discussed on the basis of the above results. The experimental procedure involved many compounds, such as (2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate (cas: 144490-03-9) .
(2R,3S,4S,5S)-5-(Acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate(cas:144490-03-9 Electric Literature of C13H18O9) is an isomer of 1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose (T283100) which is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem