204700-16-3Relevant academic research and scientific papers
β-homoalanyl PNAs: Synthesis and indication of higher ordered structures
Diederichsen,Schmitt
, p. 302 - 305 (1998)
Self-pairing complexes with extraordinarily high stability are formed by β-PNAs with four to six units of the nucleo-β-amino acid 1. The key step in the synthesis is a Mitsunobu reaction between a β-homoserine and a purine derivative.
β-Homoalanyl-PNA: A Special Case of β-Peptides with β-Sheet-Like Backbone Conformation; Organization in Higher Ordered Structures
Diederichsen, Ulf,Schmitt, Harald W.
, p. 827 - 835 (2007/10/03)
Although β-homoalanyl peptide nucleic acid oligomers possess a β-peptide backbone, they contain nucleobases in their side chains and are thus an interesting special case of β-peptides. These nucleobases are mainly responsible for the formation of secondary structures through base pairing and stacking. We have investigated the pairing properties of β-homoalanyl-PNA oligomers using adenine and 7-carbaadenine. Simple model studies indicate the existence of Watson-Crick and Hoogsteen pairing planes as an intrinsic structural feature of purinyl β-PNA. As a consequence, the adeninyl-β-PNA hexamer and pentamer form higher ordered structures and the 7-carbaadenine-β-PNA hexamer, which lacks a Hoogsteen pairing site, pairs as a double strand. The synthesis of adeninyl and carbaadeninyl β-nucleoamino acids and their oligomerization is described. Pairing mode and strand orientation were investigated through experiment and simple model studies. In the context of β-peptides the β-PNA oligomers for the most part tend to exist as double strands and prefer the extended β-sheet-like backbone conformation which provides an interesting structure motif in addition to the 31-helix observed for β-peptides.
