Nucleic acid chemistry

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Editor: Prof. Hans-Achim Wagenknecht
Karlsruhe Institute of Technology
 
Since the discovery of the structure of the DNA double helix in 1953, we know that DNA is of critical importance, carrying the genetic information for all living organisms. Only a few years later the first reports on the chemical synthesis of oligonucleotides appeared. During the past years the field of nucleic acid chemistry has expanded dramatically: natural and artificial functionalities, as well as probes, markers or other biologically active molecules, can be synthetically introduced into DNA (as well as RNA) by preparing the corresponding artificial DNA and RNA building blocks. Although nucleic acid chemistry appears to be a mature part of organic and bioorganic chemistry, the many questions that are still being raised give sufficient motivation to continue to synthesize new nucleic acid probes. Moreover, in addition to their biological functionality, DNA and RNA are considered as increasingly important architectures and scaffolds for two- and three-dimensional objects, networks and materials for nanosciences.
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Nucleic acid chemistry

  • Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2014, 10, 2928–2929, doi:10.3762/bjoc.10.311

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Published 10 Dec 2014

A new building block for DNA network formation by self-assembly and polymerase chain reaction

  • Holger Bußkamp,
  • Sascha Keller,
  • Marta Robotta,
  • Malte Drescher and
  • Andreas Marx

Beilstein J. Org. Chem. 2014, 10, 1037–1046, doi:10.3762/bjoc.10.104

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Published 07 May 2014

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA2DNA triplexes

  • Alex Manicardi,
  • Lucia Guidi,
  • Alice Ghidini and
  • Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

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Published 02 Jul 2014

Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity

  • Christian B. Winiger,
  • Simon M. Langenegger,
  • Oleg Khorev and
  • Robert Häner

Beilstein J. Org. Chem. 2014, 10, 1589–1595, doi:10.3762/bjoc.10.164

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Published 11 Jul 2014

Structure/affinity studies in the bicyclo-DNA series: Synthesis and properties of oligonucleotides containing bcen-T and iso-tricyclo-T nucleosides

  • Branislav Dugovic,
  • Michael Wagner and
  • Christian J. Leumann

Beilstein J. Org. Chem. 2014, 10, 1840–1847, doi:10.3762/bjoc.10.194

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Published 12 Aug 2014

Synthesis of a bifunctional cytidine derivative and its conjugation to RNA for in vitro selection of a cytidine deaminase ribozyme

  • Nico Rublack and
  • Sabine Müller

Beilstein J. Org. Chem. 2014, 10, 1906–1913, doi:10.3762/bjoc.10.198

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Published 15 Aug 2014

Syntheses of 15N-labeled pre-queuosine nucleobase derivatives

  • Jasmin Levic and
  • Ronald Micura

Beilstein J. Org. Chem. 2014, 10, 1914–1918, doi:10.3762/bjoc.10.199

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Published 18 Aug 2014

Pyrrolidine nucleotide analogs with a tunable conformation

  • Lenka Poštová Slavětínská,
  • Dominik Rejman and
  • Radek Pohl

Beilstein J. Org. Chem. 2014, 10, 1967–1980, doi:10.3762/bjoc.10.205

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Published 22 Aug 2014

Synthesis of phosphoramidites of isoGNA, an isomer of glycerol nucleic acid

  • Keunsoo Kim,
  • Venkateshwarlu Punna,
  • Phaneendrasai Karri and
  • Ramanarayanan Krishnamurthy

Beilstein J. Org. Chem. 2014, 10, 2131–2138, doi:10.3762/bjoc.10.220

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Published 08 Sep 2014

Second generation silver(I)-mediated imidazole base pairs

  • Susanne Hensel,
  • Nicole Megger,
  • Kristina Schweizer and
  • Jens Müller

Beilstein J. Org. Chem. 2014, 10, 2139–2144, doi:10.3762/bjoc.10.221

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Published 09 Sep 2014

Synthesis and optical properties of pyrrolidinyl peptide nucleic acid carrying a clicked Nile red label

  • Nattawut Yotapan,
  • Chayan Charoenpakdee,
  • Pawinee Wathanathavorn,
  • Boonsong Ditmangklo,
  • Hans-Achim Wagenknecht and
  • Tirayut Vilaivan

Beilstein J. Org. Chem. 2014, 10, 2166–2174, doi:10.3762/bjoc.10.224

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Published 11 Sep 2014

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

  • Marijana Radić Stojković,
  • Marko Škugor,
  • Łukasz Dudek,
  • Jarosław Grolik,
  • Julita Eilmes and
  • Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

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Published 12 Sep 2014

Solution phase synthesis of short oligoribonucleotides on a precipitative tetrapodal support

  • Alejandro Gimenez Molina,
  • Amit M. Jabgunde,
  • Pasi Virta and
  • Harri Lönnberg

Beilstein J. Org. Chem. 2014, 10, 2279–2285, doi:10.3762/bjoc.10.237

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Published 29 Sep 2014

Reversibly locked thionucleobase pairs in DNA to study base flipping enzymes

  • Christine Beuck and
  • Elmar Weinhold

Beilstein J. Org. Chem. 2014, 10, 2293–2306, doi:10.3762/bjoc.10.239

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Published 01 Oct 2014

Specific DNA duplex formation at an artificial lipid bilayer: fluorescence microscopy after Sybr Green I staining

  • Emma Werz and
  • Helmut Rosemeyer

Beilstein J. Org. Chem. 2014, 10, 2307–2321, doi:10.3762/bjoc.10.240

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Published 02 Oct 2014

Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

  • Vicky Gheerardijn,
  • Jos Van den Begin and
  • Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

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Published 04 Nov 2014

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

  • Lidija-Marija Tumir,
  • Marijana Radić Stojković and
  • Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

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Published 10 Dec 2014

A comparative study of the interactions of cationic hetarenes with quadruplex-DNA forming oligonucleotide sequences of the insulin-linked polymorphic region (ILPR)

  • Darinka Dzubiel,
  • Heiko Ihmels,
  • Mohamed M. A. Mahmoud and
  • Laura Thomas

Beilstein J. Org. Chem. 2014, 10, 2963–2974, doi:10.3762/bjoc.10.314

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Published 11 Dec 2014

NAA-modified DNA oligonucleotides with zwitterionic backbones: stereoselective synthesis of A–T phosphoramidite building blocks

  • Boris Schmidtgall,
  • Claudia Höbartner and
  • Christian Ducho

Beilstein J. Org. Chem. 2015, 11, 50–60, doi:10.3762/bjoc.11.8

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Published 13 Jan 2015

Synthesis of dinucleoside acylphosphonites by phosphonodiamidite chemistry and investigation of phosphorus epimerization

  • William H. Hersh

Beilstein J. Org. Chem. 2015, 11, 184–191, doi:10.3762/bjoc.11.19

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Published 30 Jan 2015

TEMPO-derived spin labels linked to the nucleobases adenine and cytosine for probing local structural perturbations in DNA by EPR spectroscopy

  • Dnyaneshwar B. Gophane and
  • Snorri Th. Sigurdsson

Beilstein J. Org. Chem. 2015, 11, 219–227, doi:10.3762/bjoc.11.24

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Published 09 Feb 2015

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

  • Roberto Romeo,
  • Caterina Carnovale,
  • Salvatore V. Giofrè,
  • Maria A. Chiacchio,
  • Adriana Garozzo,
  • Emanuele Amata,
  • Giovanni Romeo and
  • Ugo Chiacchio

Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38

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Published 09 Mar 2015

A procedure for the preparation and isolation of nucleoside-5’-diphosphates

  • Heidi J. Korhonen,
  • Hannah L. Bolt and
  • David R. W. Hodgson

Beilstein J. Org. Chem. 2015, 11, 469–472, doi:10.3762/bjoc.11.52

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Published 10 Apr 2015

Sequence-specific RNA cleavage by PNA conjugates of the metal-free artificial ribonuclease tris(2-aminobenzimidazole)

  • Friederike Danneberg,
  • Alice Ghidini,
  • Plamena Dogandzhiyski,
  • Elisabeth Kalden,
  • Roger Strömberg and
  • Michael W. Göbel

Beilstein J. Org. Chem. 2015, 11, 493–498, doi:10.3762/bjoc.11.55

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Published 16 Apr 2015
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Published 01 Jun 2015
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