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Peptide nucleic acids (PNA) derived from N-(N-methylaminoethyl)glycine. Synthesis, hybridization and structural properties

Haaima, Gerald and Rasmussen, Hanne and Schmidt, Günther and Jensen, Dorte K. and Kastrup, Jette Sandholm and Stafshede, Pernilla Wittung and Nordén, Bengt and Buchardt, Ole and Nielsen, Peter E. (1999) Peptide nucleic acids (PNA) derived from N-(N-methylaminoethyl)glycine. Synthesis, hybridization and structural properties. New Journal of Chemistry, 23 (8). pp. 833-840. ISSN 1144-0546. doi:10.1039/a902091h.

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Backbone N-methylated peptide nucleic acids (PNAs) containing the four nucleobases adenine, cytosine, guanine and thymine were synthesized via solid phase peptide oligomerization. The oligomers bind to their complementary target with a thermal stability that is 1.5–4.5°C lower per "N-methyl nucleobase unit' [dependent on the number and position(s) of the N-methyl] than that of unmodified PNA. However, even fully N-methyl modified PNAs bind as efficiently to DNA or RNA targets as DNA itself. Furthermore, the hybridization efficiency per N-methyl unit in a PNA decreased with increasing N-methyl content, and the effect was more pronounced when the N-methyl backbone units are present in the Hoogsteen versus the Watson–Crick strand in (PNA)2-DNA triplexes. Interestingly, CD spectral analyses indicate that 30% (3 out of ten) substitution with N-methyl nucleobases did not alter the structure of PNA-DNA (or RNA) duplexes or (PNA)2-DNA triplexes, and likewise CD spectroscopy and X-ray crystallography showed no major structural differences between N-methylated (30%) and unmodified PNA-PNA duplexes. However, PNA-DNA duplexes as well as triplexes adopted a different conformation when formed with all-N-methyl PNAs.

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Additional Information:© Royal Society of Chemistry 1999 Received (in Cambridge, UK) 15th March 1999, Accepted 24th May 1999 The technical assistance of Annette Jørgensen and Brian Rosenberg is gratefully acknowledged. The work was supported by grants from The Danish National Research Foundation, PharmaBiotec and The Lundbeck Foundation.
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ID Code:3165
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Deposited On:17 May 2006
Last Modified:08 Nov 2021 19:53

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