The use of dialkyl acetals in the N-alkylation of 8-oxoadenosine and guanosine. Mechanistic studies and rate determination

Ayele, Tewoderos M; Chang, Stephanie J.; Resendiz, Marino J. E.

doi:10.1016/j.tetlet.2015.06.002

Cited by 5 publications

(5 citation statements)

References 26 publications

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“…DMF‐DMA has been used in the methylation of functionalized nucleic acids. Methylation of 8‐oxoadenosine with DMF‐DMA occurs at the N7 position through two pathways: 1) formylation with the key intermediate 4 to afford intermediate 5 , followed by an intramolecular pathway to form the methylated product 6 ; and 2) intermolecular reaction of 8‐oxoadenosine with 4 to afford product 6 (Scheme ) …”

Section: Methylation By Using Conventional Reagentsmentioning

confidence: 99%

“…Methylation of 8-oxoadenosine with DMF-DMA occurs at the N7 positiont hrough two pathways:1 )formylation with the key intermediate 4 to afford intermediate 5, followed by an intramolecular pathway to form the methylated product 6;a nd 2) intermolecular reactiono f8 -oxoadenosine with 4 to afford product 6 (Scheme 2). [24] Fairley et al at AstraZeneca used DMF-DMA for the methylation of NH-containing groups in heterocycles. They discovered that the optimal reaction temperature varied according to the calculated pK a values of substrates (Table 1).…”

Section: Methylation By Using Conventional Reagentsmentioning

confidence: 99%

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Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Chen

2018

Chemistry A European J

186

121

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Methylation is a well‐known structural modification in organic and medicinal chemistry. This review summarizes recent advances in methylation by categorizing specific methylation reagents. The challenges of mono N‐methylation of aliphatic amines and N‐methylation of peptides are discussed. This review will be useful for chemists wanting to select the appropriate reagents for methylation chemistry. Based on the large diversity of methylation reagents and their wide scope, this review also broadens perspectives on which strategies to select for utilizing a particular methylation, resulting in an increased flexibility in synthetic route planning.

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Section: Methylation By Using Conventional Reagentsmentioning

confidence: 99%

Section: Methylation By Using Conventional Reagentsmentioning

confidence: 99%

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Chen

2018

Chemistry A European J

186

121

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“…(TMOF) [83] 、原乙酸三甲酯65 (TMOA)、N,N-二甲基甲酰胺二甲基乙缩醛66 (DMF-DMA) [84,85] 、N,N-二甲基乙酰胺二甲基乙缩醛67 (DMA-DMA) [86] 等(图29).…”

Section: 除此之外甲醚类甲基试剂还有原甲酸三甲酯64unclassified

Recent advances in methylating agents

et al. 2020

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Methyl group is not only an important building block of biologically active molecules and drug molecules, but also the important structural unit of complex molecules. Methylation of complex molecules is generally achieved through methylating reactions, which mainly include nucleophilic attack, electrophilic attack, and radical pathways. This review summarized the literatures of the past few decades and covered commonly used methylating agents used in methylation. In this review, the recently developed new methylating agents and methylation reactions are highlighted, and the reaction mechanisms are also detailed discussed. We expect that this review will inspire others to devote their research in the field of methylation.

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“…[65] This study led to the N6-dimethylformamidine (dmf) protection along with in situ addition of am ethyl-, ethyl-, n-propyl, nbutyl, tert-butyl, or benzyl-group to theN 7-position by stirring in the presence of the corresponding acetals and N,N-dimethylformamide with heat. To probe the reactivity of the N7-position, alkylation of 8-oxoA was carried out under mild conditions in the presence of severald imethylformamidedialkyl acetals.…”

Section: Syntheses Approachesmentioning

confidence: 99%

“…8‐OxoA has also been used as a model to elucidate reaction mechanisms. To probe the reactivity of the N7‐position, alkylation of 8‐oxoA was carried out under mild conditions in the presence of several dimethylformamidedialkyl acetals . This study led to the N6‐dimethylformamidine (dmf) protection along with in situ addition of a methyl‐, ethyl‐, n ‐propyl, n‐ butyl, tert‐ butyl, or benzyl‐group to the N7‐position by stirring in the presence of the corresponding acetals and N , N ‐dimethylformamide with heat.…”

Section: Synthesis and Natural Productsmentioning

confidence: 99%

8‐Oxo‐7,8‐dihydroadenine and 8‐Oxo‐7,8‐dihydroadenosine—Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives

Choi

Chang

Gibala

et al. 2017

Chemistry A European J

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A description and history of the role that 8-oxo-7,8-dihydroadenine (8-oxoAde) and 8-oxo-7,8-dihydroadenosine (8-oxoA) have in various fields has been compiled. This Review focusses on 1) the formation of this oxidatively generated modification in RNA, its interactions with other biopolymers, and its potential role in the development/progression of disease; 2) the independent synthesis and incorporation of this modified nucleoside into oligonucleotides of RNA to display the progress that has been made in establishing its behavior in biologically relevant systems; 3) reported synthetic routes, which date back to 1890, along with the progress that has been made in the total synthesis of the nucleobase, nucleoside, and their corresponding derivatives; and 4) the isolation, total synthesis, and biological activity of natural products containing these moieties as the backbone. The current state of research regarding this oxidatively generated lesion as well as its importance in the context of RNA, natural products, and potential as drug derivatives is illustrated using all available examples reported to date.

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The use of dialkyl acetals in the N-alkylation of 8-oxoadenosine and guanosine. Mechanistic studies and rate determination

Cited by 5 publications

References 26 publications

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Recent advances in methylating agents

8‐Oxo‐7,8‐dihydroadenine and 8‐Oxo‐7,8‐dihydroadenosine—Chemistry, Structure, and Function in RNA and Their Presence in Natural Products and Potential Drug Derivatives

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