Effective synthesis of C-nucleosides with 2′,4′-BNA modification

Hari, Yoshiyuki; Obika, Satoshi; Sakaki, Minako; Morio, Ken Ichiro; Yamagata, Yuriko; Imanishi, Takeshi

doi:10.1016/s0040-4020(02)00226-0

Cited by 35 publications

(34 citation statements)

References 49 publications

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“…In allele-specific PCR, the specificity of oligonucleotides can be dramatically improved using synthetic nucleic acid analogues such as locked nucleic acid (LNA, Chart 1) [7][8][9][10][11][12][13][14]. LNA's unique bicyclic structure allows it to adopt the RNA mimicking N-type furanose conformation.…”

Section: Enzyme-based Detection Of Snpmentioning

confidence: 99%

Toward Non-Enzymatic Ultrasensitive Identification of Single Nucleotide Polymorphisms by Optical Methods

Astakhova¹

2014

Chemosensors

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Single nucleotide polymorphisms (SNPs) are single nucleotide variations which comprise the most wide spread source of genetic diversity in the genome. Currently, SNPs serve as markers for genetic predispositions, clinically evident disorders and diverse drug responses. Present SNP diagnostics are primarily based on enzymatic reactions in different formats including sequencing, polymerase-chain reaction (PCR) and microarrays. In these assays, the enzymes are applied to address the required sensitivity and specificity when detecting SNP. On the other hand, the development of enzyme-free, simple and robust SNP sensing methods is in a constant focus in research and industry as such assays allow rapid and reproducible SNP diagnostics without the need for expensive equipment and reagents. An ideal method for detection of SNP would entail mixing a DNA or RNA target with a probe to directly obtain a signal. Current assays are still not fulfilling these requirements, although remarkable progress has been achieved in recent years. In this review, current SNP sensing approaches are described with a main focus on recently introduced direct, enzyme-free and ultrasensitive SNP sensing by optical methods.

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Section: Enzyme-based Detection Of Snpmentioning

confidence: 99%

Toward Non-Enzymatic Ultrasensitive Identification of Single Nucleotide Polymorphisms by Optical Methods

Astakhova¹

2014

Chemosensors

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“…Furthermore, the preparation of the organolithium derivative followed by interchange using magnesium dibromide can also be used. The generated imidazolylmagnesium halide has been employed in addition reactions to carbonyl compounds for the preparation, for example, of ligands for the a 2D adrenergic receptor [218], sugar-mimic glycosidase inhibitors [219] or C-nucleosides [220]. It has also been used in acylation reactions with esters in the synthesis of pilocarpine analogues [221] or with Weinreb amides such as 145 (Scheme 10.67) [222].…”

Section: Magnesium Azolesmentioning

confidence: 99%

Five‐Membered Heterocycles: 1,3‐Azoles

Revuelta¹,

Machetti²,

Cicchi³

2011

Modern Heterocyclic Chemistry

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“…12). 66,67) This synthetic route involves a stereoselective coupling reaction between the aldehyde and the lithium or magnesium derivative of aromatic heterocycles, followed by a ring-closure reaction using Mitsunobu conditions. Using this synthetic scheme, various C-nucleoside derivatives of 2Ј,4Ј-BNA/LNA have been synthesized.…”

Section: Extension Of Target Sequence In the Parallel Motif Triplexmentioning

confidence: 99%

“…Using this synthetic scheme, various C-nucleoside derivatives of 2Ј,4Ј-BNA/LNA have been synthesized. [66][67][68] Very recently, we have succeeded in preparing the 2Ј,4Ј-BNA/LNA analogues bearing phenols as a nucleobase to recognize a TA or UA interruption in a homopurine-homopyrimidine DNA sequence (Fig. 13).…”

Section: Extension Of Target Sequence In the Parallel Motif Triplexmentioning

confidence: 99%

Development of Bridged Nucleic Acid Analogues for Antigene Technology

Obika

2004

CHEMICAL & PHARMACEUTICAL BULLETIN

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In the last decade, increased efforts have been directed toward the development of oligonucleotide-based technologies for genome analyses, diagnostics, or therapeutics. Among them, an antigene strategy is one promising technology to regulate gene expression in living cells. Stable triplex formation between the triplex-forming oligonucleotide (TFO) and the target double-stranded DNA (dsDNA) is fundamental to the antigene strategy. However, there are two major drawbacks in triplex formation by a natural TFO: low stability of the triplex and limitations of the target DNA sequence. To overcome these problems, we have developed various bridged nucleic acids (BNAs), and found that the 2,4-BNA modification of oligonucleotides strongly promotes parallel motif triplex formation under physiological conditions. Some nucleobase analogues to extend the target DNA sequence were designed, synthesized, and introduced into the 2,4-BNA structure. The obtained 2,4-BNA derivatives with unnatural nucleobases effectively recognized a pyrimidine-purine interruption in the target dsDNA. Some other examples of nucleic acid analogues for stable triplex formation and extension of the target DNA sequence are also summarized.

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Effective synthesis of C-nucleosides with 2′,4′-BNA modification

Cited by 35 publications

References 49 publications

Toward Non-Enzymatic Ultrasensitive Identification of Single Nucleotide Polymorphisms by Optical Methods

Toward Non-Enzymatic Ultrasensitive Identification of Single Nucleotide Polymorphisms by Optical Methods

Five‐Membered Heterocycles: 1,3‐Azoles

Development of Bridged Nucleic Acid Analogues for Antigene Technology

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