One-Step Synthesis for Orn-Val with High Molecular Weight and Low Polydispersity by Ugi Four-Component Condensation

Junhui Ma; Nan Ma; Jun Liu; Qiongqiong Zhu; Yan Tang; Lei Wang; Yan Yan; Ting Yue; Meiyu Shao; Wei Zhang

doi:10.1021/acsbiomaterials.4c01379

One-Step Synthesis for Orn-Val with High Molecular Weight and Low Polydispersity by Ugi Four-Component Condensation

ACS Biomater Sci Eng. 2024 Nov 27. doi: 10.1021/acsbiomaterials.4c01379. Online ahead of print.

Authors

Junhui Ma^{1

2}, Nan Ma¹, Jun Liu¹, Qiongqiong Zhu¹, Yan Tang¹, Lei Wang^{1

2}, Yan Yan¹, Ting Yue¹, Meiyu Shao¹, Wei Zhang¹

Affiliations

¹ Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
² University of Chinese Academy of Sciences, Beijing 100049, China.

PMID: 39603821
DOI: 10.1021/acsbiomaterials.4c01379

Abstract

Basic amino acid alternating copolymers exhibit exceptional antimicrobial properties and biosafety, yet their application is restricted by the complexity of the synthesis process and low molecular weight (M_n = 1000). In this study, we synthesized a basic amino acid alternating copolymer (Orn-Val) in only one step by the Ugi four-component condensation (Ugi'4CC), achieving high molecular weight (M_n = 20,000) and narrow polydispersity (PDI ≤ 1.10). Furthermore, we observed that factors such as the feed ratio, reaction solvent, and pH significantly influenced the molecular weight and polydispersity of MPE-Orn-Val-Cbz. Moreover, the structure of potassium isocyanate also significantly affected the molecular weight and polydispersity of the products. And it was also demonstrated that the obtained Orn-Val demonstrated excellent antimicrobial properties and biocompatibility. Therefore, this method effectively addresses the limitations associated with the complex synthesis process and low molecular weight of amino acid alternating copolymers.

Keywords: MPE-Orn-Val-Cbz; Orn-Val; Ugi’4CC; molecular weight; polydispersity.