Folding and assembly of macromolecules is an important principle in protein fiber- and disease-formation. We here report on the synthesis and investigation of multisegmented hybrid-polymers in which different single- or oligo-amino acids are repetitively imbedded into a non-interacting alkyl-chain. The synthesis of polymers containing oligo-amino acids (BnAsp, BnGlu, H-Lys(Z)-OH, Leu, Aib, ACHC)-elements was accomplished by ADMET polymerization, using a combination of ring-opening-polymerization (ROP) of N-carboxyanhydrides and acyclic diene metathesis (ADMET) polymerization. Fractionation by preparative gel permeation chromatography generated narrowly dispersed polymers, enabling to investigate the chain length-dependent secondary structure formation of the oligo-(BnAspn, BnGlun, H-Lys(Z)-OHn), both in solution and the solid state. A distinct transition from α-helices to β-sheets in HFIP-solution was observed for oligo-(BnAspn), whereas oligo-(BnGlun) esters in the solid state stabilize preferably into β-sheets with increasing chain length and temperature, similar to amyloid-proteins. Polymers containing single amino acids (BnAsp, BnGlu, H-Lys(Z)-OH, Leu, Aib, ACHC) showed a defect-dependent crystallization behavior as investigated via DSC- and WAXS-measurement. The synthesis of the polymers was accomplished by ADMET polymerization and hydrogenation of the chosen N- and C-terminus ω-alkene-chain functionalized amino acids. Nonpolar AA (Leu, Aib, ACHC) generated completely amorphous polymers, whereas partial crystalline polymers for polar AA (BnAsp, BnGlu, H-Lys(Z)-OH) were obtained.

Synthesis and investigation of multisegmented hybrid-polymers based on single/oligo-amino acids

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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