Reaction of ninhydrin with cytosine derivatives

Shapiro, Robert; Agarwal, S. C.

doi:10.1021/ja01004a045

Cited by 32 publications

(18 citation statements)

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“…Ninhydrin reacts with cytosine, cytidine, and cytidine nucleotides to form products 510a-d (Scheme 163). 534 The use of this reaction was suggested to modify cytosine residues of nucleic acids. Upon treatment with boiling acetic anhydride, followed by an aqueous work-up, acetylation of 510a affords a triacetyl derivative to which structure 511a was assigned.…”

Section: Synthesis Of Seven-membered Heterocyclesmentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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Section: Synthesis Of Seven-membered Heterocyclesmentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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“…reaction time as compared to the standard procedure, and the workup was much simplified. Thiation of tri-0-benzoyl-4-thiouridine (147) or its 5-methyl derivative with phosphorus pentasulfide in tetralin at 160°C afforded, after debenzoylation, 2,4-dithiouridine(372) (149) and 5-methyl-2,4-dithiouridine. (367) Amination of (149) afforded 2-thiocytidine and its N 4 -methyl and N 4 -dimethyl derivatives (150), the former being a minor nucleoside from certain tRNAs.…”

Section: Substitution At C-4 and C-2 And Related Reactionsmentioning

confidence: 99%

“…Cytosine and cytidine phosphates gave the polynuclear products, whereas uridine was unreactive toward ninhydrin under similar reaction conditions. (149) …”

mentioning

confidence: 99%

Synthesis and Reaction of Pyrimidine Nucleosides

Ueda

1988

Chemistry of Nucleosides and Nucleotides

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“…It has been regarded as the gold standard for 5‐MeCyt detection and therefore widely used to detect 5‐MeCyt at single base resolution in a large variety of cell types and disease models. This method is based on the selective bisulfite‐mediated deamination of Cyt to uracil in the presence of 5‐MeCyt, which remains unchanged as a result of slower deamination . The sites of epigenetic markers can be revealed by comparison of the output of conventional sequencing methods before and after bisulfite treatment, as Cyt will be sequenced as thymine (T), and 5‐MeCyt as Cyt .…”

Section: Introductionmentioning

confidence: 99%

The deamination mechanism of 5,6‐dihydrocytosine and 5,6‐dihydro‐5‐methylcytosine under typical bisulfite condition

Jin

Shi

Song

et al. 2019

J of Physical Organic Chem

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The discrimination of DNA methylation could make more complicated with the appearance of these minor bases. The conventional bisulfite sequencing faces with the tremendous challenge in the discrimination of DNA methylation. Therefore, the improved and modification bisulfite sequencing has been conducted to raise the reaction selectivity. The key mechanism for these bisulfite sequencing is the reaction of nucleic acids with HSO3− under acidic conditions. The C5═C6 bonds of 5‐methylcytosine (5‐MeCyt) and cytosine (Cyt) have been modified to improve the difference of activation free energies in bisulfite conditions. Because of this, the hydrolytic deamination of DHCytN3+ (paths A and B) and 5‐DHMeCytN3+ isomers (equatorial and axial conformers, paths C and D) has been explored in the presence of the HSO3− group. The activation free energies (ΔGs≠) of DHCytN3+ and 5‐DHMeCytN3+ equatorial conformer paths exhibit no obvious difference, which increases difficulties in differentiating cytosine from 5‐methylcytosine under bisulfite conditions. Meanwhile, the difference of ΔGs≠ between the 5‐DHMeCytN3+ axial conformer and DHCytN3+ is consistent with the experimental results, where the calculated deamination rate is lower for 5,6‐dihydro‐5‐methylcytosine than for 5,6‐dihydrocytosine. And by extrapolation, the differentiating Cyt from 5‐MeCyt may have a greater possibility by bisulfite treatment. These results have high expectations for the experimental scientists to explore new methods to avoid the formation of the 5‐DHMeCytN3+ equatorial conformer. Furthermore, the rate constant with Wigner tunneling correction for paths A, C, and D are in good agreement with uncorrected results.

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Reaction of ninhydrin with cytosine derivatives

Cited by 32 publications

References 0 publications

Ninhydrin in synthesis of heterocyclic compounds

Ninhydrin in synthesis of heterocyclic compounds

Synthesis and Reaction of Pyrimidine Nucleosides

The deamination mechanism of 5,6‐dihydrocytosine and 5,6‐dihydro‐5‐methylcytosine under typical bisulfite condition

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