Literature DB >> 16048318

Synthesis of gamma-substituted peptide nucleic acids: a new place to attach fluorophores without affecting DNA binding.

Ethan A Englund1, Daniel H Appella.   

Abstract

Molecular beacon strategies using PNA are currently restricted to fluorophore attachment to the ends of the PNA. We report the synthesis of PNA oligomers wherein fluorophores can be attached to the PNA backbone from novel gamma-lysine PNA monomers. Oligomers incorporating the modified PNA showed comparable thermal stability to the corresponding aegPNA oligomer with DNA. When the modified PNA oligomer was annealed with complementary DNA, the fluorescence intensity increased 4-fold over the unbound PNA. [structure: see text]

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Year:  2005        PMID: 16048318     DOI: 10.1021/ol051143z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  18 in total

Review 1.  Insights on chiral, backbone modified peptide nucleic acids: Properties and biological activity.

Authors:  Maria Moccia; Mauro F A Adamo; Michele Saviano
Journal:  Artif DNA PNA XNA       Date:  2016-01-11

2.  DNA-templated polymerization of side-chain-functionalized peptide nucleic acid aldehydes.

Authors:  Ralph E Kleiner; Yevgeny Brudno; Michael E Birnbaum; David R Liu
Journal:  J Am Chem Soc       Date:  2008-03-15       Impact factor: 15.419

3.  PNA-Based Multivalent Scaffolds Activate the Dopamine D2 Receptor.

Authors:  Andrew V Dix; Jennie L Conroy; Kara M George Rosenker; David R Sibley; Daniel H Appella
Journal:  ACS Med Chem Lett       Date:  2015-03-13       Impact factor: 4.345

4.  Conformational constraints of cyclopentane peptide nucleic acids facilitate tunable binding to DNA.

Authors:  Hongchao Zheng; Istvan Botos; Victor Clausse; Herman Nikolayevskiy; Elizabeth E Rastede; Munira F Fouz; Sharlyn J Mazur; Daniel H Appella
Journal:  Nucleic Acids Res       Date:  2021-01-25       Impact factor: 16.971

5.  Synthesis and characterization of conformationally preorganized, (R)-diethylene glycol-containing γ-peptide nucleic acids with superior hybridization properties and water solubility.

Authors:  Bichismita Sahu; Iulia Sacui; Srinivas Rapireddy; Kimberly J Zanotti; Raman Bahal; Bruce A Armitage; Danith H Ly
Journal:  J Org Chem       Date:  2011-06-15       Impact factor: 4.354

6.  Purification and assembly of thermostable Cy5 labeled γ-PNAs into a 3D DNA nanocage.

Authors:  Justin D Flory; Trey Johnson; Chad D Simmons; Su Lin; Giovanna Ghirlanda; Petra Fromme
Journal:  Artif DNA PNA XNA       Date:  2014-12-15

7.  Crystal structure of chiral gammaPNA with complementary DNA strand: insights into the stability and specificity of recognition and conformational preorganization.

Authors:  Joanne I Yeh; Boris Shivachev; Srinivas Rapireddy; Matthew J Crawford; Roberto R Gil; Shoucheng Du; Marcela Madrid; Danith H Ly
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

8.  Multivalent LKγ-PNA oligomers bind to a human telomere DNA G-rich sequence to form quadruplexes.

Authors:  Pankaj Gupta; Elizabeth E Rastede; Daniel H Appella
Journal:  Bioorg Med Chem Lett       Date:  2015-07-29       Impact factor: 2.823

9.  Synthesis of peptide nucleic acid FRET probes via an orthogonally protected building block for post-synthetic labeling of peptide nucleic acids at the 5-position of uracil.

Authors:  Bereket Y Oquare; John-Stephen Taylor
Journal:  Bioconjug Chem       Date:  2008-11-19       Impact factor: 4.774

10.  Synthesis of conformationally preorganized and cell-permeable guanidine-based gamma-peptide nucleic acids (gammaGPNAs).

Authors:  Bichismita Sahu; Venugopal Chenna; Kira L Lathrop; Sufi M Thomas; Gerald Zon; Kenneth J Livak; Danith H Ly
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

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