Abstract
Homochirality, an interesting phenomenon of life, is mainly an unresolved problem and was thought to be a property of living matter. Herein, we show that artificial β‐peptides have the tendency toward homochiral diastereoselective chain elongation. Chain‐length‐dependent stereochemical discrimination was investigated in the synthesis of foldamers with various side chains and secondary structures. It was found that there is a strong tendency toward the synthesis of homochiral oligomers. The size of the side chain drastically influenced the selectivity of the stereodiscriminative chain‐elongation reaction. It is noteworthy that water as the co‐solvent increases the selectivity. Such behavior is a novel fundamental biomimetic property of foldamers with a potential of future industrial application.
Highlights
Homochirality, an interesting phenomenon of life, is mainly an unresolved problem and was thought to be a property of living matter
Homochirality is an inherent property of vital polymers, for example, peptides, proteins, RNA, DNA, as well as oligo- and polysaccharides.[1]
It is still not clear whether homochirality is a result of an autocatalytic procedure[2] or if it originates from extraterrestrial optically active non-racemic mixtures.[3]
Summary
A clear collision was found between the helices of oligomer 7 building the membrane segment and the investigated compound shown in Figure 2 b. This interaction hinders and blocks the heterochiral chain elongation, and, the formation of homochiral oligomers is favored. In non-aqueous solvent systems, these compounds favored the formation of the heterochiral construct; whereas, in the presence of water, the opposite homochiral oligomers were preferred. In the case of oligomers composed of trans-ACPC, trans-ACHC, or l-Leu residues, the longer chain length provided higher DE values in the presence of water. The results gained in this fundamental study might provide the basis for industrial synthesis of b-peptides
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