-
Biochemistry Dec 1982The cancer chemotherapeutic drug cis-diamminedichloroplatinum (II) (cis-DDP) was reacted with deoxyribonucleosides, and the products were separated by high-pressure...
The cancer chemotherapeutic drug cis-diamminedichloroplatinum (II) (cis-DDP) was reacted with deoxyribonucleosides, and the products were separated by high-pressure liquid chromatography and characterized by 1H nuclear magnetic resonance. Monofunctional platination occurred at N(3) of cytidine, N(7) of guanosine, N(1) of adenosine, and N(7) of adenosine. Bifunctional platination occurred with guanosine N(7) to N(7), adenosine N(7) to N(7), and adenosine N(1) to N(7). In addition, mixed bifunctional products N(7) of guanosine-N(1) of adenosine and N(7) of guanosine-N(7) of adenosine were obtained. No bifunctional adducts were obtained that contained cytidine, presumably due to steric hindrance as trans-DDP did cross-link two cytidine residues. Similarly, no adenosine N(1) to N(1) was detected with cis-DDP. The only other products detected were obtained at high levels of cis-DDP and probably represented polymeric forms in which platinum chelates to itself.
Topics: Chromatography, High Pressure Liquid; Cisplatin; Deoxyribonucleosides
PubMed: 6891601
DOI: 10.1021/bi00269a018 -
Bioscience, Biotechnology, and... Apr 20032-Deoxyribose 5-phosphate was produced from acetaldehyde and dihydroxyacetone phosphate via D-glyceraldehyde 3-phosphate by Klebsiella pneumoniae B-4-4 through...
2-Deoxyribose 5-phosphate was produced from acetaldehyde and dihydroxyacetone phosphate via D-glyceraldehyde 3-phosphate by Klebsiella pneumoniae B-4-4 through deoxyriboaldolase- and triosephosphate isomerase-catalyzing reactions. Under the optimum conditions, 98.7 mM 2-deoxyribose 5-phosphate was produced from 200 mM acetaldehyde and 117 mM dihydroxyacetone phosphate in 2 h with a molar yield of 84%. The 2-deoxyriobse 5-phosphate produced was directly transformed to 2'-deoxyribonucleoside by phosphopentomutase- and nucleoside phosphorylase-catalyzing reactions.
Topics: Acetaldehyde; Deoxyribonucleosides; Klebsiella pneumoniae; Pentosyltransferases; Phosphotransferases; Ribosemonophosphates; Sugar Phosphates; Trioses
PubMed: 12784646
DOI: 10.1271/bbb.67.933 -
Nucleic Acids Research Mar 198513C-enriched deoxyribonucleosides have been isolated from the DNA of Algal cells grown in an atmosphere of 90% 13C-labelled carbon dioxide. The 13C enriched DNA was...
13C-enriched deoxyribonucleosides have been isolated from the DNA of Algal cells grown in an atmosphere of 90% 13C-labelled carbon dioxide. The 13C enriched DNA was quantitatively hydrolysed with DNase I, snake venom phosphodiesterase I and alkaline phosphatase of intestinal mucosa. The resulting deoxyribonucleosides were separated by preparative reversed-phase high pressure liquid chromatography in 60 minutes with detection by ultraviolet absorption at 254 nm. The final products were obtained in milligram quantities in high purity and in high yield. The 1H resonances of the base and sugar protons of these deoxyribonucleosides appear as well resolved multiplets in the 600 MHz NMR spectrum, due to the extensive 1H-13C couplings. Similarly, the 13C resonances of these deoxyribonucleosides appear as multiplets in the 75.5 MHz 13C NMR spectrum, due to 13C-13C couplings. The 1H-13C and 13C-13C coupling constants were also measured and tabulated. The isotopic enrichment of 13C these deoxyribonucleosides was obtained by integration of the 1H and/or 13C NMR spectra. It was found that the enrichment varied from carbon to carbon and species to species in the range of 70-89%, suggesting differential uptake and assimilation of 90% 13CO2 during metabolism pathways. This protocol provides experimentally useful quantities of 13C-enriched deoxyribonucleosides, which may be incorporated into site-specifically labeled oligonucleotides by chemical synthesis.
Topics: Carbon Isotopes; Chromatography, High Pressure Liquid; Deoxyribonucleosides; Eukaryota; Magnetic Resonance Spectroscopy
PubMed: 4000954
DOI: 10.1093/nar/13.6.2097 -
European Journal of Biochemistry Jan 1982In order to obtain basic knowledge of the salvage pathways for DNA synthesis, the ability of Brevibacterium ammoniagenes ATCC 6872 and Micrococcus luteus ATCC 15932 for...
In order to obtain basic knowledge of the salvage pathways for DNA synthesis, the ability of Brevibacterium ammoniagenes ATCC 6872 and Micrococcus luteus ATCC 15932 for incorporation of nucleobases and nucleosides was investigated. Only adenine and uracil are incorporated by B. ammoniagenes, whereas M. luteus additionally can utilize deoxyadenosine and, less efficiently, thymidine. In M. luteus, the demonstration of deoxyadenosine kinase and thymidine kinase explains the incorporation data. Uptake of thymidine is of short duration because of rapid breakdown of exogenously supplied thymidine to thymine. At a 540-fold excess pyrimidine deoxyribonucleosides inhibit 14C incorporation from thymidine nearly totally and purine deoxyribonucleosides cut by half the uptake rate, probably by interfering with transport of thymidine. However, as no cessation of thymidine incorporation occurs at these concentrations of purine deoxyribonucleosides, incorporation is finally enhanced. During the initial period of this reduced uptake considerable protection of thymidine from breakdown to thymine is provided by deoxyguanosine, but not by deoxyadenosine. At a 108-fold excess there is actually no inhibition of thymidine uptake by deoxyguanosine and only an insignificant impairment by deoxyadenosine resulting in an ultimate enhancement of 14C incorporation up to 20% of the exogenously supplied thymidine. As there is no salvage pathway for thymidine in B. ammoniagenes due to the absence of thymidine kinase, labelling with adenine and hydrolyzing of the 'contaminated' RNA fraction with 1 M KOH is recommended for measurements of overall DNA synthesis in this strain.
Topics: Brevibacterium; DNA, Bacterial; Deoxyribonucleosides; Micrococcus; Phosphotransferases; Phosphotransferases (Alcohol Group Acceptor); Thymidine Kinase
PubMed: 6277626
DOI: 10.1111/j.1432-1033.1982.tb05795.x -
Mikrochimica Acta Oct 2022A novel strategy is reported to access high-performance nanozymes via the self-coordination of ferrocyanides ([Fe(CN)]) onto the surface of the CuBiS (CBS) nanorods....
A novel strategy is reported to access high-performance nanozymes via the self-coordination of ferrocyanides ([Fe(CN)]) onto the surface of the CuBiS (CBS) nanorods. Notably, the in situ formed nanozymes had high catalytic activity, good stability, low cost, and easy mass production. The formed nanozyme catalyzed the oxidation of the typical chromogenic substrate of 3,3',5,5'-tetramethylbenzidine (TMB) with a distinctive absorption peak at 652 nm, accompanied by a blue color development. Moreover, the attachment of deoxyribonucleoside 5'-monophosphates (dNMP) beforehand onto the surface of CBS prevented coordination of ferrocyanides and resulted in the tunable formation of the nanozyme, thereby enabling the construction of an exquisite biosensing platform. Taking the aptasensing of chloramphenicol (CAP) as an example, the engineered nanozyme allowed the construction of a homogenous, label-free, and high-performance bioassay in terms of its convenience and high sensitivity. Under the optimal conditions, changes in the absorption intensity at 652 nm for the oxidized TMB provides a good linear correlation with the logarithm of CAP concentrations in the range 0.1 pM to 100 nM, and the limit of detection was 0.033 pM (calculated from 3σ/s). Considering a vast number of bioreactions can be connected to dNMP production, we expect the engineerable nanozyme as a universal signal transduction scaffold for versatile applications in bioassays. Through the attachment of deoxyribonucleoside 5'-monophosphate (dNMP) on the surface of CBS to regulate the generation of self-coordinated nanozyme CBS/BiHCF, a homogeneous, label-free, and high-performance universal aptasensing platform was constructed.
Topics: Benzidines; Chloramphenicol; Chromogenic Compounds; Deoxyribonucleosides; Ferrocyanides; Nanotubes
PubMed: 36251095
DOI: 10.1007/s00604-022-05524-x -
Nucleic Acids Research Sep 2019A new approach to single-molecule DNA sequencing in which dNTPs, released by pyrophosphorolysis from the strand to be sequenced, are captured in microdroplets and read...
A new approach to single-molecule DNA sequencing in which dNTPs, released by pyrophosphorolysis from the strand to be sequenced, are captured in microdroplets and read directly could have substantial advantages over current sequence-by-synthesis methods; however, there is no existing method sensitive enough to detect a single nucleotide in a microdroplet. We have developed a method for dNTP detection based on an enzymatic two-stage reaction which produces a robust fluorescent signal that is easy to detect and process. By taking advantage of the inherent specificity of DNA polymerases and ligases, coupled with volume restriction in microdroplets, this method allows us to simultaneously detect the presence of and distinguish between, the four natural dNTPs at the single-molecule level, with negligible cross-talk.
Topics: DNA-Directed DNA Polymerase; Deoxyribonucleosides; Deoxyribonucleotides; High-Throughput Nucleotide Sequencing; Limit of Detection; Microscopy, Fluorescence; Oligodeoxyribonucleotides; Sensitivity and Specificity; Sequence Analysis, DNA
PubMed: 31318971
DOI: 10.1093/nar/gkz611 -
Organic Letters Jul 2018The synthesis and characterization of a universal and fluorescent nucleoside, 4-cyanoindole-2'-deoxyribonucleoside (4CIN), and its incorporation into DNA is described....
The synthesis and characterization of a universal and fluorescent nucleoside, 4-cyanoindole-2'-deoxyribonucleoside (4CIN), and its incorporation into DNA is described. 4CIN is a highly efficient fluorophore with quantum yields >0.90 in water. When incorporated into duplex DNA, 4CIN pairs equivalently with native nucleobases and has uniquely high quantum yields ranging from 0.15 to 0.31 depending on sequence and hybridization contexts, surpassing that of 2-aminopurine, the prototypical nucleoside fluorophore. 4CIN constitutes a new isomorphic nucleoside for diverse applications.
Topics: DNA; Deoxyribonucleosides; Fluorescent Dyes; Indoles; Isomerism; Light; Nitriles; Nucleic Acid Hybridization
PubMed: 29989830
DOI: 10.1021/acs.orglett.8b01746 -
Methods in Molecular Biology (Clifton,... 2000
Topics: Boronic Acids; Chromatography, Affinity; Deoxyribonucleosides; Glycoproteins; Ribonucleosides
PubMed: 10857091
DOI: 10.1007/978-1-60327-261-2_12 -
Organic Letters Jul 2012A general, green, and efficient Brønsted acid-catalyzed glycosylation serves as a key step in the one-flow, multistep syntheses of several important...
A general, green, and efficient Brønsted acid-catalyzed glycosylation serves as a key step in the one-flow, multistep syntheses of several important 5'-deoxyribonucleoside pharmaceuticals.
Topics: Acetonitriles; Catalysis; Deoxyribonucleosides; Glycosylation; Mesylates; Molecular Structure; Pyridinium Compounds
PubMed: 22694250
DOI: 10.1021/ol301324g -
Organic & Biomolecular Chemistry Jul 20132-Bromo-6-chloro- and 6-bromo-2-chloropyridin-3-yl deoxyribonucleosides were prepared by the Heck coupling of bromo-chloro-iodopyridines with TBS-protected deoxyribose...
2-Bromo-6-chloro- and 6-bromo-2-chloropyridin-3-yl deoxyribonucleosides were prepared by the Heck coupling of bromo-chloro-iodopyridines with TBS-protected deoxyribose glycal. Some of their Pd-catalyzed cross-coupling reactions proceeded chemoselectively at the position of the bromine, whereas nucleophilic substitutions were unselective and gave mixtures of products. The mono-substituted intermediates were used for another coupling or nucleophilic substitution giving rise to a small library of title 2,6-disubstituted pyridine C-deoxyribonucleosides. The title nucleosides did not exert antiviral or cytostatic effects.
Topics: Chemistry Techniques, Synthetic; Deoxyribonucleosides; Pyridines; Substrate Specificity
PubMed: 23760109
DOI: 10.1039/c3ob40774h