Triazole-Linked Analogue of Deoxyribonucleic Acid (<sup>TL</sup>DNA): Design, Synthesis, and Double-Strand Formation with Natural DNA

Isobe, Hiroyuki; Fujino, Tomoko; Yamazaki, N.; Guillot‐Nieckowski, Marine; Nakamura, Eiichi

doi:10.1021/ol801230k

Cited by 180 publications

(122 citation statements)

References 31 publications

(30 reference statements)

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“…Binding to a fucose-specific bacterial lectin was determined by an enzyme-linked lectin amplification competition assay. The IC 50 values were 10-20 times better than for monovalent L-fucose and suggest a ''macromolecular'' rather than a ''cluster'' effect. Glyco-oligonucleotide conjugates, each exhibiting two mannose and two galactose residues, were efficiently synthesised by two successive microwave-assisted 1,3-dipolar cycloadditions.…”

Section: Oligonucleotide Labelling With Fluorophores and Carbohydratesmentioning

confidence: 82%

Click chemistry with DNA

2010

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Section: Oligonucleotide Labelling With Fluorophores and Carbohydratesmentioning

confidence: 82%

Click chemistry with DNA

2010

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“…Regardless of the detailed mechanisms, our results indicate that the artificial DNA linker is remarkably biocompatible, and investigations are underway to solve the highresolution structure of a DNA duplex containing this triazole linkage and determine its effects on DNA conformation and dynamics. Other DNA backbone mimics have been made (40,41), but in these constructs the entire DNA strand was modified, precluding their use in PCR or any biological application requiring enzymatic processing. Nevertheless, these studies point to other interesting triazole analogues that could in principle be incorporated into DNA via chemical ligation as discrete units and investigated as potential biocompatible linkages.…”

Section: Resultsmentioning

confidence: 99%

Biocompatible artificial DNA linker that is read through by DNA polymerases and is functional in Escherichia coli

El‐Sagheer

Sanzone

Gao

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

140

158

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A triazole mimic of a DNA phosphodiester linkage has been produced by templated chemical ligation of oligonucleotides functionalized with 5′-azide and 3′-alkyne. The individual azide and alkyne oligonucleotides were synthesized by standard phosphoramidite methods and assembled using a straightforward ligation procedure. This highly efficient chemical equivalent of enzymatic DNA ligation has been used to assemble a 300-mer from three 100-mer oligonucleotides, demonstrating the total chemical synthesis of very long oligonucleotides. The base sequences of the DNA strands containing this artificial linkage were copied during PCR with high fidelity and a gene containing the triazole linker was functional in Escherichia coli.replicated in bacteria | triazole DNA backbone | click chemistry | CuAAC reaction S olid-phase DNA synthesis (1, 2) is an advanced technology that has led to pioneering discoveries in biology and nanotechnology (3-8). Although automated solid-phase phosphoramidite synthesis is highly efficient, the accumulation of modifications (mutations) and failure sequences caused by side-reactions and imperfect coupling imposes a practical limit of around 150 bases on the length of oligonucleotides that can be made. Consequently very long synthetic oligonucleotides are not suitable for use in biological applications that require sequence fidelity, so combinations of shorter sequences are normally used in PCRmediated gene assembly (9, 10). This enzymatic method of DNA synthesis has the intrinsic limitation that site-specific chemical modifications can only be introduced in the primer regions of the resulting constructs. Certain unnatural analogues can be inserted throughout the PCR amplicon via modified dNTPs, but this process is essentially uncontrolled and does not allow combinations of different modifications to be incorporated at specific loci. Therefore, for biological studies, important epigenetic and mutagenic bases such as 5-methyl dC, 5-hydroxymethyl dC and 8-oxo dG are normally put into short oligonucleotides and subsequently inserted into larger DNA strands by enzymatic ligation. Templated enzymatic ligation of oligonucleotides can be used to produce large DNA fragments, but this is best carried out on a small scale. In addition, some modified bases are not tolerated by ligase enzymes. Enzymatic methods of gene synthesis are extremely important in biology, but a purely chemical method for the assembly of large DNA molecules would be an interesting and valuable addition to current tools, with the advantages of scalability, flexibility, and orthogonality.It has proved challenging to achieve clean and efficient chemical ligation of canonical DNA, although significant progress has been made using cyanogen bromide as a coupling agent (11,12). An interesting alternative approach is to design a chemical linkage that mimics the natural phosphodiester bond, and that can be formed in high yield in aqueous media from functional groups that are orthogonal to those naturally present in DNA. This goal has been pa...

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“…The amino ethyl glycyl (aeg) thymine monomer for initial coupling was synthesized by the reported procedure. 22 All new compounds were characterized by 1 H, 13 C NMR, IR and mass spectral data. synthesis of triazole based pna oligomers on solid support.…”

Section: Resultsmentioning

confidence: 99%

“…[8][9][10] Triazoles have been shown to be good isosteres of peptide bond and hence used to design backbone of cyclotetrapeptide mimics, 11 peptoid oligomers 12 and even to replace the phosphate linkage in DNA. 13,14 Such triazole based backbone oligomers have been shown to display protein-like secondary structural motifs, inducing turns and β-strands. 15,16 In oligonucleotides, they can be used to crosslink the two termini to give rise to dumbbell structures 17 and linear triazolamers form pharmacophores recognizing tetraplex structures.…”

Section: Introductionmentioning

confidence: 99%

1,4-linked 1,2,3-Triazole containing chimeric PNA (aeg-TzNA) oligomers

Devi

Ganesh

2010

Artificial DNA: PNA & XNA

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Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA

Cited by 180 publications

References 31 publications

Click chemistry with DNA

Click chemistry with DNA

Biocompatible artificial DNA linker that is read through by DNA polymerases and is functional in Escherichia coli

1,4-linked 1,2,3-Triazole containing chimeric PNA (aeg-TzNA) oligomers

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Triazole-Linked Analogue of Deoxyribonucleic Acid (TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA

Cited by 180 publications

References 31 publications

Click chemistry with DNA

Click chemistry with DNA

Biocompatible artificial DNA linker that is read through by DNA polymerases and is functional in Escherichia coli

1,4-linked 1,2,3-Triazole containing chimeric PNA (aeg-TzNA) oligomers

Contact Info

Product

Resources

About

Triazole-Linked Analogue of Deoxyribonucleic Acid (^TLDNA): Design, Synthesis, and Double-Strand Formation with Natural DNA