168264-14-0Relevant academic research and scientific papers
Side chain homologation of alanyl peptide nucleic acids: Pairing selectivity and stacking
Diederichsen, Ulf,Weicherding, Daniel,Diezemann, Nicola
, p. 1058 - 1066 (2007/10/03)
Alanyl peptide nucleic acids (alanyl-PNAs) are oligomers based on a regular peptide backbone with alternating configuration of the amino acids. All side chains are modified by covalently linked nucleobases. Alanyl-PNAs form very rigid, well defined, and l
α-PNA: A Novel Peptide Nucleic Acid Analogue of DNA
Howarth, Nicola M.,Wakelin, Laurence P. G.
, p. 5441 - 5450 (2007/10/03)
Peptide nucleic acid (PNA) analogues of DNA have attracted interest as potential pharmacological regulators of gene expression since they have the capacity to invade duplex DNA forming Watson-Crick base paired PNA:DNA heteroduplexes. Unfortunately, strand invasion is limited to homopurine and homopyrimidine sequences and there is the need to explore further PNA analogues for the purpose of expanding the strand invasion alphabet. Accordingly, we have designed a true peptide mimic of DNA (designated α-PNA) involving novel L-α-amino acids, with side chains comprising the four DNA bases attached via an ethylene linkage, interspaced with glycine. The four base-containing amino acids have been synthesized from N-Boc-L-homoserine, via alkylation of the appropriate base with the key intermediate (S)-2-(N-Boc-amino)-4-bromobutyric acid methyl ester followed by hydrolysis. These amino acids have been incorporated into α-PNA oligomers using both solution and solid phase methods.
