Solid phase synthesis of directly linked PNA-DNA-hybrids

Bergmann, Frank; Bannwarth, Willi; Tam, Steve

doi:10.1016/0040-4039(95)01405-7

Cited by 64 publications

(65 citation statements)

References 4 publications

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“…A further variation of the Fmoc PNA synthesis strategy has been described by Bergmann et al [68] for the synthesis of PNA/DNA chimeras. An Fmoc/acyl protecting group strategy was proposed for the N unit through an ester group.…”

Section: The 9-fluorenylmethyloxycarbonyl (Fmoc) Protecting Group Strmentioning

confidence: 98%

“…The benzoyl protecting groups of deoxycytidine-containing chimeras were removed by treatment with concentrated ammonia at 55 o C overnight. Bergmann et al [68] synthesized PNA/DNA chimeras of types (I) and (III). A sarcosine-linked CPG solid support was used for the synthesis of homopyrimidine (pseudo-5')-PNA-(linker)-DNA-3' chimeras.…”

Section: Synthesis Of Pna/dna Chimerasmentioning

confidence: 98%

“…The use of Fmoc/acyl-protected PNA building blocks for the synthesis of mixed sequences with acid-sensitive purine nucleosides in the DNA part was suggested. [68] However, neither the preparation of these monomeric building blocks, nor their use in the synthesis of purine-containing mixed sequences have been described in detail.…”

Section: Synthesis Of Pna/dna Chimerasmentioning

confidence: 99%

“…The synthesis cycle consisted of cleavage of the N-terminal Boc temporary protecting group with TFA, followed by monomer coupling to the N terminus, which Figure 13. Supports for the solid-phase synthesis of PNA and PNA/DNA chimeras: a) Boc-Lys(Cl-Cbz)-MBHA-polystyrene; [6,8,27] b) dimethoxytrityl-12-hydroxydodecanoic acid-CPG; [68] c) monomethoxytrityl aminohexylsuccinate-CPG; [25,26] d) Breipohl linker. [25] proceeded in 94 ± 99 % yield.…”

Section: Monomers With Chiral or Olefinic Backbonesmentioning

confidence: 99%

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PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

Uhlmann¹,

Peyman²,

Breipohl³

et al. 1998

Angewandte Chemie International Edition

398

217

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The astonishing discovery that peptide nucleic acids (PNAs, B=nucleobase), in spite of their drastic structural difference to natural DNA, are better nucleic acid mimetics than many other oligonucleotides has resulted in an explosion of research into this class of compounds. The synthesis, physical properties, and biological interactions of PNAs as well as their chimeras with DNA and RNA are summarized here.

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Section: The 9-fluorenylmethyloxycarbonyl (Fmoc) Protecting Group Strmentioning

confidence: 98%

Section: Synthesis Of Pna/dna Chimerasmentioning

confidence: 98%

Section: Synthesis Of Pna/dna Chimerasmentioning

confidence: 99%

Section: Monomers With Chiral or Olefinic Backbonesmentioning

confidence: 99%

See 2 more Smart Citations

PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

Uhlmann¹,

Peyman²,

Breipohl³

et al. 1998

Angewandte Chemie International Edition

398

217

View full text Add to dashboard Cite

show abstract

“…[21][22][23] PNA solubility is often sequence-dependent, which usually leads to several restrictions in PNA probe design and can be improved by incorporation of Lys residues or ethylene glycol linkers (eg1 ¼ 8 amino-2-6 dioxaoctanoic acid). 18,[21][22][23][24] Efimov et al 25,26 have developed a novel oligonucleotide mimic, a dimeric oligomer that consists of a phosphonate analog of PNA (pPNA) and a PNA-like monomer based on a trans-4-hydroxyl-L-proline (HypNA). The introduction of negative charges into the PNA backbone yields excellent solubility without hindering its other properties.…”

Section: Introductionmentioning

confidence: 99%

Combination of a new generation of PNAs with a peptide-based carrier enables efficient targeting of cell cycle progression

et al. 2004

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The design of potent systems for the delivery of charged and noncharged molecules that target genes of interest remains a challenge. We describe a novel technology that combines a new generation of peptide nucleic acids (PNAs), or HypNApPNAs, with a new noncovalent peptide-based delivery system, Pep-2, which promotes efficient delivery of PNAs into several cell lines. We have validated the potential of this technology by showing that Pep2-mediated delivery of an antisense HypNApPNA chimera directed specifically against cyclin B1 induces rapid and robust downregulation of its protein levels and efficiently blocks cell cycle progression of several cell lines, as well as proliferation of cells derived from a breast cancer. Pep-2-based delivery system was shown to be 100-fold more efficient in delivering HypNA-pPNAs than classical cationic lipidbased methods. Whereas Pep-2 is essential for improving the bioavailability of PNAs and HypNA-pPNAs, the latter contribute significantly to the efficiency and specificity of the biological response. We have found that Pep-2/HypNA-pPNA strategy promotes potent antisense effects, which are approximately 25-fold greater than with classical antisense oligonucleotide directed specifically against the same cyclin B1 target. Taken together, these data demonstrate that peptide-mediated delivery of HypNA-pPNAs constitutes a very promising technology for therapeutic applications.

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PNAs: synthetische Polyamidnucleinsäuren mit außergewöhnlichen Bindungseigenschaften

Uhlmann¹,

Peyman²,

Breipohl³

et al. 1998

Angewandte Chemie

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Äußerst überraschend war die Erkenntnis, daß Peptidnucleinsäuren (PNAs, B=Nucleobase) trotz ihrer drastisch vom natürlichen DNA‐Rückgrat abweichenden Struktur besser als die meisten Oligonucleotidderivate als Nucleinsäuremimetica genutzt werden können. Die Synthese, physikalischen Eigenschaften und biologischen Wechselwirkungen sowohl der PNAs als auch ihrer Chimären mit DNA und RNA werden hier zusammenfassend beschrieben.

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Solid phase synthesis of directly linked PNA-DNA-hybrids

Cited by 64 publications

References 4 publications

PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

Combination of a new generation of PNAs with a peptide-based carrier enables efficient targeting of cell cycle progression

PNAs: synthetische Polyamidnucleinsäuren mit außergewöhnlichen Bindungseigenschaften

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