Structure of the Nucleic Acids

Kochetkov, Nikolay K.; Budovskii, E. I.

doi:10.1007/978-1-4757-0543-0_2

Cited by 12 publications

(24 citation statements)

References 404 publications

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“…For uracil derivatives the reaction takes place only under basic conditions [64][65][66][67][68][69][70][71][72][73] .Sodium bisulfite…”

Section: Deuteration At C5 Of Uracil and Cytosine Derivativesmentioning

confidence: 99%

“…However, in alkaline medium the hydrolysis of the N-glycosidic bond 64 and deamination 64,67,69,70 can take place. The use of (NH 4 ) 2 SO 3 instead of NaHSO 3 results in more rapid deamination 70 .…”

Section: Scheme 2 R = H or Ribofuranos-1-ylmentioning

confidence: 99%

“…Uridine-5-2 H can be isolated in good yield with high isotope incorporation upon treatment with 2-mercaptoethylamine in 2 H 2 O either at room or at elevated temperature 64,65 . Similar catalytic activity has been observed for glutathione 57 and cysteine 56,61 59 upon formation of a C6 adduct with 2'-deoxyuridine monophosphate.…”

Section: Scheme 2 R = H or Ribofuranos-1-ylmentioning

confidence: 99%

“…Protons linked to C8 of purine derivatives can be exchanged more rapidly compared to C5 and C6 of pyrimidines and C2 of purines 64 . The first observation of ex- change of the proton attached to C8 with a deuteron has been done in 2 H 2 O at >100 ?C 80,81 .…”

Section: Deuteration At C8 Of Adenine and Guanine Derivativesmentioning

confidence: 99%

“…The proton attached to C2 of adenines does not undergo exchange in 2 H 2 O in a facile manner as that of the C8 64 . Deuterium can be introduced at C2 of adenine via different routes [89][90][91] .…”

Section: Deuteration At C2 Of Adenine Derivativesmentioning

confidence: 99%

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The Synthesis of Deuterionucleosides

Földesi

Trifonova

Kundu

et al. 2000

Nucleosides, Nucleotides and Nucleic Acids

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“…For uracil derivatives the reaction takes place only under basic conditions [64][65][66][67][68][69][70][71][72][73] .Sodium bisulfite…”

Section: Deuteration At C5 Of Uracil and Cytosine Derivativesmentioning

confidence: 99%

Section: Scheme 2 R = H or Ribofuranos-1-ylmentioning

confidence: 99%

Section: Scheme 2 R = H or Ribofuranos-1-ylmentioning

confidence: 99%

Section: Deuteration At C8 Of Adenine and Guanine Derivativesmentioning

confidence: 99%

Section: Deuteration At C2 Of Adenine Derivativesmentioning

confidence: 99%

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The Synthesis of Deuterionucleosides

Földesi

Trifonova

Kundu

et al. 2000

Nucleosides, Nucleotides and Nucleic Acids

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Site‐specific laser modification (cleavage) of oligodeoxynucleotides

et al. 1989

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Sequence-specific photomodification of oligodeoxynucleotide pAGAGTATTGACTTA ("a target") has been carried out with the aid of complementary fluorescent probes. Such a probe consisted of oligodeoxynucleotide pAATACTCT and a chromophore group attached to its 5' end. Three different derivatives of ethidium bromide were used as a chromophore. The photomodification was induced by nitrogen laser radiation (337 nm, 15 MW/cm2). The irradiation induces the following photodamages: target cleavage at the specific binding site with a cutting off of the 8-mer from its 5' end (yield up to 12%), formation of specific covalent adduct target-probe with a yield of 20-70%, and piperidine-sensitive target modifications with a 7-27% yield (for different chromophores). The total yield of specific photodamages of all kinds is 50-80%. The target cleavage and generation of piperidine-sensitive modifications are optically nonlinear processes. Piperidine treatment of the irradiated samples led to specific cleavage of the target with the yield up to 40%. All kinds of observed modifications are not influenced by high concentrations of free radical scavengers: 1.3M tBuOH and 10 mM cystamine. The pattern of cleavage indicates that the most probable position of the chromophore is between T8 and G9 of the target, i.e., the chromophore stacks on top of the last A.T base pair of the duplex. The aggregate of evidence is in agreement with the mechanism of nonlinear photomodification (the cleavage and generation of piperidine-sensitive modifications) based on the transfer of two-photon excitation energy from the chromophore to the target.

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7‐Deaza purine bases offer a higher ion stability in the analysis of dna by matrix‐assisted laser desorption/ionization mass spectrometry

Kirpekar¹,

Nordhoff²,

Kristiansen³

et al. 1995

Rapid Comm Mass Spectrometry

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Oligodeoxynucleotides which contain 7-deaza analogues of the normal purine nucleotides have been synthesized both enzymatically and chemically. When subjected to matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) analysis, the modified samples offer both higher stability and increased sensitivity compared to otherwise identical unmodified oligodeoxynucleotides. In view of these observations, models for the fragmentation of oligodeoxynucleotides in MALDI-MS with positive ion detection mode are presented. Additionally, the potential use of 7-deaza purine nucleotides in the MALDI-MS analysis of DNA sequencing reactions is discussed.

show abstract

Structure of the Nucleic Acids

Cited by 12 publications

References 404 publications

The Synthesis of Deuterionucleosides

The Synthesis of Deuterionucleosides

Site‐specific laser modification (cleavage) of oligodeoxynucleotides

7‐Deaza purine bases offer a higher ion stability in the analysis of dna by matrix‐assisted laser desorption/ionization mass spectrometry

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