Synthesis and properties of 2′-O,4′-C-methyleneoxymethylene bridged nucleic acid

Hari, Yoshiyuki; Obika, Satoshi; Ohnishi, Ryo; Eguchi, Ken; Osaki, Tomohisa; Ohishi, Hirofumi; Imanishi, Takeshi

doi:10.1016/j.bmc.2005.09.020

Cited by 69 publications

(37 citation statements)

References 22 publications

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“…[14] A Further analogue prepared by Imanishi et al is the 2',4'-BNA COC (10), which has improved nuclease resistance and forms more stable heteroduplexes with single stranded RNA, but less stable heteroduplexes with single stranded DNA. [15] 2',4'-BNA NC (11) on the other hand forms more stable heteroduplexes with RNA and DNA, enhances the stability of triplexes formed with double stranded DNA (when X = H and Me) and improves nuclease resistance. [16] Wengel and colleagues also showed that bipyridyl functionalised 2'-amino-LNA (12) could be used to modulate the stability of duplexes by varying divalent metal ion concentration and the position of the modification(s) in the backbone of the duplex (Scheme 3).…”

Section: Sugar Modificationsmentioning

confidence: 98%

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

2009

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Although known for more than a century, bromine trifluoride is not a common reagent in day to day research work in organic chemistry. Its tendency to react exothermically with solvents containing Lewis base elements such as water, acetone or ethers distanced it from the mind of many. Still, under the proper conditions, it can perform quite a few selective reactions which are difficult to achieve by other reagents. We discuss in this review reactions which have been published in the last 30 years. They consist of fluorinating heteroatoms, substituting carbon‐halogen bonds with carbon‐fluorine bonds, syntheses of anesthetics, construction of the trifluoromethyl (CF3) and the difluoromethylene (CF2) groups, aromatic brominations and more.

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Section: Sugar Modificationsmentioning

confidence: 98%

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

2009

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“…Replacement with longer linkages has been accomplished given a CCO-linkage (ENA) [56,57], a CCN-linkage (amino-ENA) [58], and a COC-linkage [59,60]. Recently, a carbocyclic ring with a saturated CCC-linkage or an unsaturated C¼CC-linkage has been introduced [61], and even longer linkages (CCCO [57] and COCO [62]) have been studied. A review of the available NMR and X-ray data, combined with molecular modeling, demonstrates that the puckering amplitude is closely related to the number of atoms in the 2 0 -4 0 -linkage [61].…”

Section: Analogues Of Lna and Their Structural Impactmentioning

confidence: 99%

Locked Nucleic Acids: Properties, Applications, and Perspectives

Nielsen

Wengel

2008

Modified Nucleosides

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A decade has passed since the introduction of locked nucleic acid (LNA) [1][2][3]. This chapter provides a review and a current status on the features and applications of LNA. Attention is focused on the structural chemistry of LNA and on its applications for therapeutics and probes. With regards to the latter point, the chapter is based on former comprehensive reviews on LNA applications [4][5][6] and, for that reason, is focused on results reported subsequently, with no intention of being comprehensive.The field of nucleic acid chemistry has evolved considerably during the past few decades, leading from synthetic developments via molecular recognition into nucleic acid-based therapeutics, powerful diagnostic probes, and modern nanobiotechnology. From the structural perspective, the central issue has been the thorough understanding of the basis for molecular recognition and the selective formation of nucleic acid complexes, initially the classic Watson-Crick-type double helix. The central creative challenge for synthetic chemists has been to design simple chemical perturbations of the natural duplex in order to increase our knowledge within nucleic acid chemical biology, and to bring this knowledge into applied nucleic acids research [7-9].The major motivation behind the design of nucleic acid analogues has, over the past two decades, been the antisense strategy aimed at the silencing of genes by strong binding towards mRNA, with or without associated RNA-cleavage. Two central problems have motivated the chemical effort: (1) the physiological instability of natural oligonucleotides; and (2) the relatively moderate affinity of short natural oligonucleotides for their RNA-targets [10,11]. If a solution to these problems -as well as to the delicate question of cellular delivery -can be found, then oligonucleotides will present unlimited therapeutic perspectives. Among the more than 1000 chemical analogues tested for these properties, a large part seems to induce a high degree of resistance towards nucleolytic degradation, although this is dependent on the sequence composition, the number and positioning of the chemical modifications within the sequence, and on the degree of perturbation compared to the natural chemical structure. On the other hand, significantly increasing the RNA-affinity of an Modified Nucleosides: in Biochemistry, Biotechnology and Medicine. Edited by Piet Herdewijn

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“…Considering this, we initially developed a nucleic acid analogue, 2 ,4 -BNA COC and found that this nucleic acid analogue provided excellent nuclease resistance property. [8] However, its hybridizing ability is lowered greatly, compared to that of 2 ,4 -BNA. Therefore, as a continued effort to develop superior BNA analogues, we designed and synthesized a novel bridged nucleic acid analogue 2 ,4 -BNA NC with N-O bridged structure.…”

Section: Introductionmentioning

confidence: 97%

2′,4′-BNA^NC: A Novel Bridged Nucleic Acid Analogue with Excellent Hybridizing and Nuclease Resistance Profiles

Rahman

Seki

Utsuki

et al. 2007

Nucleosides, Nucleotides and Nucleic Acids

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Synthesis and properties of 2′-O,4′-C-methyleneoxymethylene bridged nucleic acid

Cited by 69 publications

References 22 publications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Locked Nucleic Acids: Properties, Applications, and Perspectives

2′,4′-BNA^NC: A Novel Bridged Nucleic Acid Analogue with Excellent Hybridizing and Nuclease Resistance Profiles

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Synthesis and properties of 2′-O,4′-C-methyleneoxymethylene bridged nucleic acid

Cited by 69 publications

References 22 publications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Chemical Modification of Oligonucleotides for Therapeutic, Bioanalytical and other Applications

Locked Nucleic Acids: Properties, Applications, and Perspectives

2′,4′-BNANC: A Novel Bridged Nucleic Acid Analogue with Excellent Hybridizing and Nuclease Resistance Profiles

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Product

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2′,4′-BNA^NC: A Novel Bridged Nucleic Acid Analogue with Excellent Hybridizing and Nuclease Resistance Profiles