Nucleobase-caged peptide nucleic acids: PNA/PNA duplex destabilization and light-triggered PNA/PNA recognition

Journal of Peptide Science

Volumn 19, Issue 7, 2013, Pages 415-422

  Guha, Samit ^a   Graf, Julia ^a   Göricke, Björn ^a   Diederichsen, Ulf ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Caging group; Double strand recognition; Nucleobase pairing; Peptide nucleic acid (PNA); Photolabile protecting group

Indexed keywords

ADENINE; CYTOSINE; NUCLEIC ACID BASE; PEPTIDE NUCLEIC ACID; RESIN;

AMINO ACID SYNTHESIS; ARTICLE; BASE PAIRING; PRIORITY JOURNAL; PROTEIN CLEAVAGE; SOLID PHASE SYNTHESIS; ULTRAVIOLET IRRADIATION; ULTRAVIOLET RADIATION; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; SYNTHESIS; TEMPERATURE;

LIGHT; MOLECULAR STRUCTURE; PEPTIDE NUCLEIC ACIDS; TEMPERATURE; ULTRAVIOLET RAYS;

EID: 84878969824     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2514     Document Type: Article

References (26)

1. Klán P, Solomek T, Bochet CG, Blanc A, Givens R, Rubina M, Popik V, Kostikov A, Wirz J. Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy. Chem. Rev. 2013; 113: 119-191.
2. Deiters A. Light activation as a method of regulating and studying gene expression. Curr. Opin. Chem. Biol. 2009; 13: 678-686.
3. Mayer G, Heckel A. Biologically active molecules with a "light switch". Angew. Chem. Int. Ed. 2006; 45: 4900-4921.
4. Brieke C, Rohrbach F, Gottschalk A, Mayer G, Heckel A. Light-controlled tools. Angew. Chem. Int. Ed. 2012; 51: 8446-8476.
5. Dormán G, Prestwich GD. Using photolabile ligands in drug discovery and development. Trends Biotechnol. 2000; 18: 64-77.
6. Gatterdam V, Stoess T, Menge C, Heckel A, Tampé R. Caged glutathione - triggering protein interaction by light. Angew. Chem. Int. Ed. 2012; 51: 3960-3963.
7. Ghosn B, Haselton FR, Gee KR, Monroe WT. Control of DNA hybridization with photocleavable adducts. Photochem. Photobiol. 2005; 81: 953-959.
8. Jain PK, Shah S, Friedman SH. Patterning of gene expression using new photolabile groups applied to light activated RNAi. J. Am. Chem. Soc. 2011; 133: 440-446.
9. Srinivas O, Mitra N, Surolia A, Jayaraman N. Photoswitchable multivalent sugar ligands: synthesis, isomerization, and lectin binding studies of azobenzene-glycopyranoside derivatives. J. Am. Chem. Soc. 2002; 124: 2124-2125.
10. Scott RH, Pollock J, Ayar A, Thatcher NM, Zehavi U. Synthesis and use of caged sphingolipids. Methods Enzymol. 2000; 312: 387-400.
11. Bhushan KR. Photolabile peptide nucleic acid monomers: synthesis and photodeprotection. Synlett 2006; 13: 2130-2132.
12. Stafforst T, Hilvert D. Modulating PNA/DNA hybridization by light. Angew. Chem. Int. Ed. 2010; 49: 9998-10001.
13. Nielsen PE, Egholm M, Berg RH, Buchardt O. Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide. Science 1991; 254: 1497-1500.
14. Tomac S, Sarkar M, Ratilainen T, Wittung P, Nielsen PE, Nordén B, Gräslund A. Ionic effects on the stability and conformation of peptide nucleic acid complexes. J. Am. Chem. Soc. 1996; 118: 5544-5552.
15. Nielsen PE. Peptide Nucleic Acids, Methods and Protocols. Humana Press: Totowa, New Jersey, 2002.
16. Lygina AS, Meyenberg K, Jahn R, Diederichsen U. Transmembrane domain peptide/peptide nucleic acid hybride as a model of a SNARE protein in vesicle fusion. Angew. Chem. Int. Ed. 2011; 50: 8597-8601.
17. Walbert S, Pfleiderer W, Steiner UE. Photolabile protecting groups for nucleosides: mechanistic studies of the 2-(2-nitrophenyl)ethyl group. Helv. Chim. Acta 2001; 84: 1601-1611.
18. Pillai VNR. Photoremovable protecting groups in organic synthesis. Synthesis 1980; 1-26.
19. Pelliccioli AP, Wirz J. Photoremovable protecting groups: reaction mechanisms and applications. Photochem. Photobiol. Sci. 2002; 1: 441-458.
20. Corrie JET, Barth A, Munasinghe VRN, Trentham DR, Hutter MC. Photolytic cleavage of 1-(2-nitrophenyl)ethyl ethers involves two parallel pathways and product release is rate-limited by decomposition of a common hemiacetal intermediate. J. Am. Chem. Soc. 2003; 125: 8546-8554.
21. Kröck L, Heckel A. Photoinduced transcription by using temporarily mismatched caged oligonucleotides. Angew. Chem. Int. Ed. 2005; 44: 471-473.
22. Mayer G, Kröck L, Mikat V, Engeser M, Heckel A. Light-induced formation of G-quadruplex DNA secondary structures. Chembiochem 2005; 6: 1966-1970.
23. Rodrigues-Correia A, Koeppel MB, Schäfer F, Joshi KB, Mack T, Heckel A. Comparison of the duplex-destabilizing effects of nucleobase-caged oligonucleotides. Anal. Bioanal. Chem. 2011; 399: 441-447.
24. Nielsen PE, Egholm M. in Peptide Nucleic Acids. Horizont Scientific Press: Norfolk, 1999, 39-50.
25. Wittung P, Nielsen PE, Buchardt O, Egholm M, Nordén B. DNA-like double helix formed by peptide nucleic acid. Nature 1994; 368: 561-563.
26. Schäfer F, Joshi KB, Fichte MAH, Mack T, Wachtveitl J, Heckel A. Wavelength-selective uncaging of dA and dC residues. Org. Lett. 2011; 13: 1450-1453.