Insight into the cross-linking of synthetic polypeptide gels prepared by ring-opening polymerization using L-cystine N -carboxyanhydride

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作   者：

Utrosa, Petra;  Zagar, Ema;  Pahovnik, David; 

作者机构：

Natl Inst Chem; 

关键词：

HYDROGELS;  N -carboxyanhydride;  Cross-linking;  Ring-opening polymerization;  Synthetic polypeptide;  Homocystine;  Cystine; 

期刊名称：

European Polymer Journal

i s s n：

0014-3057

年卷期：

2024 年 204 卷

页   码：

ARTN 112707-

页   码：

摘   要：

Synthetic polypeptides have promising potential for various biomedical applications that often require a cross-linked network for stability against solvents or mechanical stress. Due to the natural occurrence and availabil-ity of the L-cystine alpha-amino acid, L-cystine N-carboxyanhydride (NCA) is commonly used as a cross-linker in the ring-opening (co)polymerization of alpha-amino acid NCAs to prepare covalently cross-linked synthetic polypeptides. In this work, we show that the L-cystine NCA tends to undergo undesired decomposition side reactions, i.e., beta-elimination and formation of 2,5-diketopiperazine, which reduce the amount of the cross-linker available and make it difficult to control the final properties of the materials prepared from it. By using the analogous L- homocystine NCA instead, the decomposition side reactions can be completely avoided. We demonstrate the cross-linking performance of L-cystine NCA compared to L-homocystine NCA by studying the corresponding gels prepared by copolymerization with gamma-benzyl-L-glutamate NCA.