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Guide Mass Spectrometry of Nucleosides and Nucleic Acids

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For Instructors Request Inspection Copy. Next, the contributors examine mass spectrometric application in the study of cyclic nucleotides in biochemical signal transduction. They analyze urinary modified nucleosides and explore DNA adducts. The book reviews recent progress in the direct MS characterization of noncovalent nucleic acid-protein complexes, explores the interaction and ionization of guanidine-derived compounds with highly acidic biomolecules, and examines quantitative identification of nucleic acids via signature digestion products detected using mass spectrometry.

The exciting developments in mass spectrometry technology have fueled incredible advances in our understanding of nucleic acids and their complexes. The contributions presented in this volume capture the range of these advances, helping to inspire new findings a Table of Contents Overview of Recent Developments in the Mass Spectrometry of Nucleic Acid and Constituents. Mass Spectrometric Analysis of Deoxyinosines. Tandem Mass Spectrometry of Nucleic Acids.

Structure Of Nucleic Acids - Structure Of DNA - Structure Of RNA - DNA Structure And RNA Structure

We provide complimentary e-inspection copies of primary textbooks to instructors considering our books for course adoption. Most VitalSource eBooks are available in a reflowable EPUB format which allows you to resize text to suit you and enables other accessibility features. Where the content of the eBook requires a specific layout, or contains maths or other special characters, the eBook will be available in PDF PBK format, which cannot be reflowed. The six amino acids selected for this study arginine, glutamic acid, threonine, methionine, phenylalanine and tryptophan have different side chains, with different chemical natures and functional groups.

When the results were compared with the data obtained from the reaction of only P-ribose and adenine, changes in the isomeric distribution of AMP were observed in all the reactions, except in the case of tryptophan, which might be attributed to conformational limitations due to the presence of tryptophan's indole-based side chain. However, a clear difference was observed in the EIC of adenosine only for the reactions including phenylalanine and threonine.

Our results show that glycosidic bonds can be simultaneously formed with three different nucleobases in a one-pot dehydration reaction under acidic conditions. The observed nucleobase exchange implies a dynamic equilibrium in the dehydration reaction, where bonds are broken and formed towards the enrichment of the most thermodynamically stable products. Glycosidic bond formation between P-ribose and the nucleobase is found to preferentially occur at the primary amine sites of the nucleobase where available , leading to non-canonical nucleobases forming as major products.


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However, reactivity at secondary amine sites also occurs, leading to a distribution of isomeric products. Furthermore, while the reaction of ribose is most likely to occur through the anomeric position, glycosidic bond formation at other positions is also possible, further increasing the number of possible isomeric products.

Canonical structures might have only appeared later as a result of further evolution building on these more abundant species. Addition of amino acids was found to significantly alter the relative intensity and distribution of product isomers, and we suggest that this is partially through competition for reactive amine sites on the nucleobase, though amino acid adducts do not account for all the changes observed.

Detection and Quantification of Modified Nucleotides in RNA Using Thin-Layer Chromatography

Since the conformation of the nucleobases in a nucleic acid is critical for hydrogen bonding and base pairing, future work will investigate how this selectivity may be tuned using different amino acids or reactive species, in order to promote specific nucleobase isomers. Glass reaction vessels were placed in the corresponding Drysyn hotplate inserts. Lids with three integrated holes were placed on each vial which facilitated the evaporation during the drying step see Supplementary Fig.

Then, 1. The previously published version of this Article contained errors in Fig. In Fig. Ruiz-Mirazo, K. Prebiotic systems chemistry: new perspectives for the origins of life. Rentergent, J. Time course analysis of enzyme-catalyzed DNA polymerization. Biochemistry 55 , — Kafri, M. The cost of protein production.

Cell Rep. Hud, N.

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Fuller, W. Studies in prebiotic synthesis. VII solid-state synthesis of purine nucleosides. Sanchez, R. V Synthesis and photoanomerization of pyrimidine nucleosides. Powner, M. Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions. Nature , — Xu, J. Bean, H. Cafferty, B. Spontaneous formation and base pairing of plausible prebiotic nucleotides in water. Fox, S. Thermal polymerization of amino-acids and production of formed microparticles on lava.

Rodriguez-Garcia, M.

Formation of oligopeptides in high yield under simple programmable conditions. Leman, L. Carbonyl sulfide—mediated prebiotic formation of peptides. Science , — Forsythe, J. Ester-mediated amide bond formation driven by wet—dry cycles: a possible path to polypeptides on the prebiotic Earth.

Surveying the sequence diversity of model prebiotic peptides by mass spectrometry. Natl Acad. USA , E—E Duncan, K. Short peptides in minimalistic biocatalysts design. Biocatalysis 1 , 67—81 Nakashima, T. Synthesis of peptides from amino acids and ATP with lysine-rich proteinoid. Gorlero, M. Ser-His catalyses the formation of peptides and PNAs.

FEBS Lett. Tyagi, S. Nonrandomness in prebiotic peptide synthesis. Jauker, M. Griesser, H. Ribonucleotides and RNA promote peptide chain growth.

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Mass Spectrometry of Nucleosides and Nucleic Acids - CRC Press Book

Amino acid-specific, ribonucleotide-promoted peptide formation in the absence of enzymes. Ura, Y. Self-assembling sequence-adaptive peptide nucleic acids. Science , 73—77 Stairs, S. Divergent prebiotic synthesis of pyrimidine and 8-oxo-purine ribonucleotides. Kim, H. Prebiotic stereoselective synthesis of purine and noncanonical pyrimidine nucleotide from nucleobases and phosphorylated carbohydrates. The MS detection response at Note that the mass values that are used only define methylcyto-sine; substitution specifically at N 4 cannot from these data be distinguished from N-3 and C-5, which are also known positions of cytosine methylation in RNA.

The conventional mass spectra acquired every 1. An oligonucleotide of M r When plotted chromatographically Fig. The experimentally measured M r of The authors are indebted to E. Bruenger and J. Rozenski for technical assistance and to P.