58-61-7Relevant articles and documents
Escherichia coli Bl21: A useful biocatalyst for the synthesis purine nucleosides
Rogert,Martinez,Porro,Lewkowicz,Iribarren
, p. 535 - 536 (2000)
E. coli BL21 cells were able to synthesize several purine nucleosides from pyrimidine ones. Kinetics and yields of this reaction showed a strong dependence on pH, temperature, reagent concentrations and weight of wet cell paste. Yields over 90% were reached in the synthesis of adenosine.
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Carter
, p. 1466,1469 (1950)
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SYNTHESIS OF 2'-5',3'-5' LINKED TRIADENYLATES
Hayakawa, Y.,Nobori, T.,Noyori, R.,Imai, J.
, p. 2623 - 2626 (1987)
2'-5',3'-5' Linked triadenylates have been synthesized by direct bisadenylylation of adenosine 2' and 3' hydroxyls with an adenosine 5'-phosphorochloridite followed by oxidation.
Efficient cleavage of adenylyl(3'-5')adenosine by triethylenetetraminecobalt(III)
Matsumoto,Komiyama
, p. 1050 - 1051 (1990)
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Gulland,Holiday
, p. 765,766,768 (1936)
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Simultaneous High-Resolution Detection of Bioenergetic Molecules using Biomimetic-Receptor Nanopore
Su, Zhuoqun,Wei, Yongfeng,Kang, Xiao-Feng
, p. 15255 - 15259 (2019)
A novel artificial receptor, heptakis-[6-deoxy-6-(2-hydroxy-3-trimethylammonion-propyl) amino]-beta-cyclomaltoheptaose, with similar functions of mitochondrial ADP/ATP carrier protein, was synthesized and harbored in the engineered α-HL (M113R)7 nanopore, forming a single-molecule biosensor for sensing bioenergetic molecules and their transformations. The strategy significantly elevates both selectivity and signal-to-noise, which enables simultaneous recognition and detection of ATP, ADP, and AMP by real-time single-molecule measurement.
New nucleoside-based polymeric supports for the solid phase synthesis of ribose-modified nucleoside analogues
De Napoli, Lorenzo,Di Fabio, Giovanni,D'Onofrio, Jennifer,Montesarchio, Daniela
, p. 1975 - 1979 (2004)
New solid supports, linking protected pyrimidine and purine nucleoside derivatives through the nucleobase, have been prepared. The support, incorporating a suitable derivative of 2′-azido, 2′-deoxyuridine, allowed the simple and efficient solid-phase synthesis of ribose-modified nucleoside and nucleic acid analogues, particularly of aminoacyl derivatives of 2′-deoxy, 2′-amino-uridine, following methodologies well established in peptide and oligonucleotide chemistry.
Utilization of real-time electrospray ionization mass spectrometry to gain further insight into the course of nucleotide degradation by intestinal alkaline phosphatase
Kaufmann, Christine M.,Grassmann, Johanna,Treutter, Dieter,Letzel, Thomas
, p. 869 - 878 (2014)
RATIONALE Related with its ability to degrade nucleotides, intestinal alkaline phosphatase (iAP) is an important participant in intestinal pH regulation and inflammatory processes. However, its activity has been investigated mainly by using artificial non-nucleotide substrates to enable the utilization of conventional colorimetric methods. To capture the degradation of the physiological nucleotide substrate of the enzyme along with arising intermediates and the final product, the enzymatic assay was adapted to mass spectrometric detection. Therewith, the drawbacks associated with colorimetric methods could be overcome. METHODS Enzymatic activity was comparatively investigated with a conventional colorimetric malachite green method and a single quadrupole mass spectrometer with an electrospray ionization source using the physiological nucleotide substrates ATP, ADP or AMP and three different pH-values in either methodological approach. By this means the enzymatic activity was assessed on the one hand by detecting the phosphate release spectrometrically at defined time points of enzymatic reaction or on the other by continuous monitoring with mass spectrometric detection. RESULTS Adaption of the enzymatic assay to mass spectrometric detection disclosed the entire course of all reaction components - substrate, intermediates and product - resulting from the degradation of substrate, thereby pointing out a stepwise removal of phosphate groups. By calculating enzymatic substrate conversion rates a distinctively slower degradation of AMP compared to ADP or ATP was revealed together with the finding of a substrate competition between ATP and ADP at alkaline pH. CONCLUSIONS The comparison of colorimetric and mass spectrometric methods to elucidate enzyme kinetics and specificity clearly underlines the advantages of mass spectrometric detection for the investigation of complex multi-component enzymatic assays. The entire course of enzymatic substrate degradation was revealed with different nucleotide substrates, thus allowing a specific monitoring of intestinal alkaline phosphatase activity. Copyright 2014 John Wiley & Sons, Ltd. Copyright
Hydrolysis of an RNA dinucleoside monophosphate by neomycin B
Kirk, Sarah R.,Tor, Yitzhak
, p. 147 - 148 (1998)
Neomycin B is shown to accelerate the phosphodiester hydrolysis of adenylyl(3′-5′)adenosine (ApA) more effectively than a simple unstructured diamine.
H-Bond activated glycosylation of nucleobases: Implications for prebiotic nucleoside synthesis
Singh, Palwinder,Singh, Amrinder,Kaur, Jagroop,Holzer, Wolfgang
, p. 3158 - 3161 (2014)
Glycosylation of nucleobases is achieved by heating metal free aqueous solution of nucleobase and sugar. It seems that abstraction of N 9/N1 H by C1′-OH promotes N 9/N1(nucleobase)-C1′ (sug
Prebiotic stereoselective synthesis of purine and noncanonical pyrimidine nucleotide from nucleobases and phosphorylated carbohydrates
Kim, Hyo-Joong,Benner, Steven A.
, p. 11315 - 11320 (2017)
According to a current RNA first model for the origin of life, RNA emerged in some form on early Earth to become the first biopolymer to support Darwinism here. Threose nucleic acid (TNA) and other polyelectrolytes are also considered as the possible first Darwinian biopolymer(s). This model is being developed by research pursuing a Discontinuous Synthesis Model (DSM) for the formation of RNA and/or TNA from precursor molecules that might have been available on early Earth from prebiotic reactions, with the goal of making the model less discontinuous. In general, this is done by examining the reactivity of isolated products from proposed steps that generate those products, with increasing complexity of the reaction mixtures in the proposed mineralogical environments. Here, we report that adenine, diaminopurine, and hypoxanthine nucleoside phosphates and a noncanonical pyrimidine nucleoside (zebularine) phosphate can be formed from the direct coupling reaction of cyclic carbohydrate phosphates with the free nucleobases. The reaction is stereoselective, giving only the β-anomer of the nucleotides within detectable limits. For purines, the coupling is also regioselective, giving the N-9 nucleotide for adenine as a major product. In the DSM, phosphorylated carbohydrates are presumed to have been available via reactions explored previously [Krishnamurthy R, Guntha S, Eschenmoser A (2000) Angew Chem Int Ed 39:2281-2285], while nucleobases are presumed to have been available from hydrogen cyanide and other nitrogenous species formed in Earth's primitive atmosphere.
S-adenosyl-L-methionine:Hydroxide adenosyltransferase: A SAM enzyme
Deng, Hai,Botting, Catherine H.,Hamilton, John T. G.,Russell, Rupert J. M.,O'Hagan, David
, p. 5357 - 5361 (2008)
(Chemical Equation Presented) Not so DUF: A DUF62 enzyme from the archaeon Pyrococcus horikoshii OT3 converts S-adenosyl-L-methionine (SAM) into adenosine through the nucleophilic attack of a hydroxide ion derived from water (see picture of the active site). The highly conserved nature of Asp68, Arg75, and His127 throughout the DUF62 protein superfamily suggests the wide-spread distribution of this novel catalytic activity in microorganisms. DUF = domain of unknown function.
Prebiotic Photochemical Coproduction of Purine Ribo- And Deoxyribonucleosides
Xu, Jianfeng,Green, Nicholas J.,Russell, David A.,Liu, Ziwei,Sutherland, John D.
supporting information, p. 14482 - 14486 (2021/09/18)
The hypothesis that life on Earth may have started with a heterogeneous nucleic acid genetic system including both RNA and DNA has attracted broad interest. The recent finding that two RNA subunits (cytidine, C, and uridine, U) and two DNA subunits (deoxyadenosine, dA, and deoxyinosine, dI) can be coproduced in the same reaction network, compatible with a consistent geological scenario, supports this theory. However, a prebiotically plausible synthesis of the missing units (purine ribonucleosides and pyrimidine deoxyribonucleosides) in a unified reaction network remains elusive. Herein, we disclose a strictly stereoselective and furanosyl-selective synthesis of purine ribonucleosides (adenosine, A, and inosine, I) and purine deoxynucleosides (dA and dI), alongside one another, via a key photochemical reaction of thioanhydroadenosine with sulfite in alkaline solution (pH 8-10). Mechanistic studies suggest an unexpected recombination of sulfite and nucleoside alkyl radicals underpins the formation of the ribo C2′-O bond. The coproduction of A, I, dA, and dI from a common intermediate, and under conditions likely to have prevailed in at least some primordial locales, is suggestive of the potential coexistence of RNA and DNA building blocks at the dawn of life.
Meteorite-catalyzed intermoleculartrans-glycosylation produces nucleosides under proton beam irradiation
Bizzarri, Bruno Mattia,Fanelli, Angelica,Kapralov, Michail,Krasavin, Eugene,Saladino, Raffaele
, p. 19258 - 19264 (2021/06/03)
Di-glycosylated adenines act as glycosyl donors in the intermoleculartrans-glycosylation of pyrimidine nucleobases under proton beam irradiation conditions. Formamide and chondrite meteorite NWA 1465 increased the yield and the selectivity of the reaction
