Synthesis of Polypeptides and Poly(α-hydroxy esters) from Aldehydes Using Strecker Synthesis

Ester Abtew; Abraham J Domb

doi:10.1021/acsomega.3c04870

Synthesis of Polypeptides and Poly(α-hydroxy esters) from Aldehydes Using Strecker Synthesis

ACS Omega. 2023 Oct 18;8(43):40407-40416. doi: 10.1021/acsomega.3c04870. eCollection 2023 Oct 31.

Authors

Ester Abtew¹, Abraham J Domb¹

Affiliation

¹ The Alex Grass Center for Drug Design & Synthesis and the Center for Cannabis Research, School of Pharmacy, Institute of Drug Research, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem 9112001, Israel.

Abstract

This report presents a versatile approach for the synthesis of new polypeptide and polyester-based biomaterials. The well-established Strecker reaction was utilized, with hexanal serving as the model aldehyde, to synthesize α-amino and α-hydroxy acids as monomer units for the polymer system. Following the formation of the corresponding amino and hydroxy acid monomers, they were subsequently converted to N-carboxy and O-carboxy-anhydrides. The resultant cyclic anhydride molecules were then polymerized via ring-opening polymerization to yield the corresponding polypeptides and polyesters. This report establishes a straightforward methodology for the synthesis of new polypeptide and poly(a-hydroxy acid)-based biomaterials, thereby expanding the existing library of polymers for various biomedical applications.