Synthesis, nucleic acid hybridization properties and molecular modelling studies of conformationally restricted 3′-O,4′-C-methylene-linked α-l-ribonucleotides

Madsen, Andreas Stahl; Hrdlicka, Patrick J.; Kumar, Shailendra; Wengel, Jesper

doi:10.1016/j.carres.2006.04.010

Cited by 6 publications

(3 citation statements)

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“…When singly incorporated into oligonucleotides, these two monomers increase the thermal stability of duplexes with complementary DNA or RNA very significantly when compared to the thermal stability of the corresponding unmodified oligonucleotides. 5 Oligonucleotides containing LNA in the wings of so-called gapmers have been shown to successfully activate RNase H and thus to mediate cleavage of targeted RNA. In addition, incorporation of several LNA nucleotides lead to a substantial increase in the stability in human serum compared to an unmodified oligonucleotide.…”

Section: Introductionmentioning

confidence: 99%

“…6 Another group of conformationally restricted nucleotides contains an oxetane ring system where the methylene bridging is linking either C1'-O2', 1,7-10 O2'-C3' 11,12 or O3'-C4'. 5,[13][14][15]. The C1'-O2' oxetane derivatives ( Fig.…”

Section: Introductionmentioning

confidence: 99%

“…9 In certain configurations this oxetane nucleotide monomer has been shown to be compatible with RNase H activity when hybridized to RNA, 2 to give protection against endonucleases, 7 and to be useful as modification in siRNA constructs. 16 Other members of the oxetane nucleotide family include oxetane nucleic acid (ONA) 13 and α-L-ONA 5 with a O3'-C4' methylene bridge (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides

et al. 2018

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Synthesis of two novel conformationally constrained bicyclic ribonucleoside phosphoramidites bearing a 2'-C-methyl substituent has been accomplished. These phosphoramidites were used to incorporate the corresponding 2'-C-methyl nucleotides into oligonucleotides and to study their effects on duplex thermal stability. Whereas the C2'-O4'-linked LNA-type derivative induced severe destabilization of duplexes formed with complementary DNA and RNA, the C3'-O4'-linked derivative induced RNA-selective hybridization with increased affinity relative to that of the unmodified DNA-based probe.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides

et al. 2018

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Exploring the Role of Chirality in Nucleic Acid Recognition

D’Alonzo¹,

Guaragna²,

Palumbo³

2011

Chemistry & Biodiversity

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The study of the base-pairing properties of nucleic acids with sugar moieties in the backbone belonging to the L-series (β-L-DNA, β-L-RNA, and their analogs) are reviewed. The major structural factors underlying the formation of stable heterochiral complexes obtained by incorporation of modified nucleotides into natural duplexes, or by hybridization between homochiral strands of opposite sense of chirality are highlighted. In addition, the perspective use of L-nucleic acids as candidates for various therapeutic applications, or as tools for both synthetic biology and etiology-oriented investigations on the structure and stereochemistry of natural nucleic acids is discussed.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006

Harvey

2010

Mass Spectrometry Reviews

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This review is the fourth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2006. The review covers fundamental studies, fragmentation of carbohydrate ions, method developments, and applications of the technique to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, glycated proteins, glycolipids from bacteria, glycosides, and various other natural products. There is a short section on the use of MALDI-TOF mass spectrometry for the study of enzymes involved in glycan processing, a section on industrial processes, particularly the development of biopharmaceuticals and a section on the use of MALDI-MS to monitor products of chemical synthesis of carbohydrates. Large carbohydrate-protein complexes and glycodendrimers are highlighted in this final section.

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Synthesis, nucleic acid hybridization properties and molecular modelling studies of conformationally restricted 3′-O,4′-C-methylene-linked α-l-ribonucleotides

Cited by 6 publications

References 50 publications

Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides

Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides

Exploring the Role of Chirality in Nucleic Acid Recognition

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006

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