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

G. Haaima ; H. Rasmussen ; G. Schmidt ; D.K. Jensen ; J. Sandholm Kastrup ; Pernilla Wittung-Stafshede (Institutionen för fysikalisk kemi) ; Bengt Nordén (Institutionen för fysikalisk kemi) ; O. Buchardt ; P.E. Nielsen
New Journal of Chemistry (1144-0546 ). Vol. 23 (1999), 8, p. 833-840.
[Artikel, refereegranskad vetenskaplig]

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 degrees 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-Ai-methyl PNAs.

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Denna post skapades 2011-02-18. Senast ändrad 2011-07-01.
CPL Pubid: 136956


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