Reactivity of pyrimidine nucleosides under the conditions of the pyrimidine sequencing reactions of Maxam and Gilbert

Duh, Jauh‐Lin; Punzalan, Rubio; Pless, Reynaldo C.

doi:10.1016/0003-2697(88)90312-0

Cited by 4 publications

(3 citation statements)

References 14 publications

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Section: General Reactivity Of Unmodified Nucleotidesmentioning

confidence: 99%

“…Nucleophilic attack here is known from the bidentate hydrazine [39], or a combination of bisulfate and a semicarbazide [40]. In both cases, the first nucleophilic attack occurs at the C6, and only then does the C4 position react [33, 39]. Using hydrogen sulfide under high pressure, cytidines can be converted into s 4 U as the result of a nucleophilic attack at the carbon 4 position [41, 42], which might be preceded by an initial nucleophilic attack at the C6.…”

Section: General Reactivity Of Unmodified Nucleotidesmentioning

confidence: 99%

See 1 more Smart Citation

Use of Specific Chemical Reagents for Detection of Modified Nucleotides in RNA

Behm‐Ansmant

Helm

Motorin

2011

Journal of Nucleic Acids

102

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Naturally occurring cellular RNAs contain an impressive number of chemically distinct modified residues which appear posttranscriptionally, as a result of specific action of the corresponding RNA modification enzymes. Over 100 different chemical modifications have been identified and characterized up to now. Identification of the chemical nature and exact position of these modifications is typically based on 2D-TLC analysis of nucleotide digests, on HPLC coupled with mass spectrometry, or on the use of primer extension by reverse transcriptase. However, many modified nucleotides are silent in reverse transcription, since the presence of additional chemical groups frequently does not change base-pairing properties. In this paper, we give a summary of various chemical approaches exploiting the specific reactivity of modified nucleotides in RNA for their detection.

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Section: General Reactivity Of Unmodified Nucleotidesmentioning

confidence: 99%

Section: General Reactivity Of Unmodified Nucleotidesmentioning

confidence: 99%

Use of Specific Chemical Reagents for Detection of Modified Nucleotides in RNA

Behm‐Ansmant

Helm

Motorin

2011

Journal of Nucleic Acids

102

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“…7 On the other hand, Duh et al described that N 3 -alkylated thymidine (uridine) moieties in oligonucleotides reacted more readily than non-alkylated species with nucleophiles, which led to degradation of the nucleobase. 8 It is likely that ammonia reacts with most of the acrylonitrile as a scavenger under standard deprotection conditions. Under our conditions, however, the lack of ammonia may cause N 3 alkylation followed by depyrimidination.…”

Section: Entrymentioning

confidence: 99%

Synthesis and properties of oligonucleotides modified with 2′-O-(2-carboxyethyl)nucleotides and their carbamoyl derivatives

et al. 2014

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2'-O-Methyl oligoribonucleotides with four kinds of 2'-O-modified uridine derivatives were synthesised. Their duplex stability, hydration behavior and exonuclease resistance were studied by spectroscopic analyses and molecular dynamics simulations. Consequently, 2'-O-modification of the uridine residue with 2-carbamoylethyl or 2-(N-methylcarbamoyl)ethyl groups resulted in a significant improvement of the exonuclease resistance without the loss of duplex stability.

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