8. June 2020

Chirality Control of Screw-Sense in Aib-Polymers: Synthesis and Helicity of Amino Acid Functionalized Polymers.

Freudenberg, J., et al. ACS Macro Letters 2020, 686-692,

2-Aminoisobutyric acid (Aib) is an essential amino acid, leading to the formation of peptAibols as microbiologically active peptides and proteins. We here report on the ring-opening polymerization (ROP) of Aib-NCA (N-carboxy-anhydrides), enabling to prepare distinct Aib-polymers up to molecular weights of 1400 g/mol with precise end-group control. The attachment of chiral (D or L)-amino acids allows to systematically investigate the helical screw-sense of poly(Aib)n, resulting in chiral induction to form either left (M)- or right (P)-handed screw-senses. The approach is extended toward a switchable, chiral azo-headgroup, able to change chirality of the attached poly(Aib)n via a light-induced trigger. Reproduced with permission. Copyright 2020©, American Chemical Society.