New chemosynthetic route to linear ε-poly-lysine

被引：72

作者：

Tao, Youhua ^{[1
]}

Chen, Xiaoyu ^{[1
]}

Jia, Fan ^{[1
]}

Wang, Shixue ^{[1
]}

Xiao, Chunsheng ^{[1
]}

Cui, Fengchao ^{[1
]}

Li, Yunqi ^{[1
]}

Bian, Zheng ^{[1
]}

Chen, Xuesi ^{[1
]}

Wang, Xianhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Changchun Inst Appl Chem, Key Lab Polymer Ecomat, Changchun 130022, Peoples R China

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 11期

基金：

中国国家自然科学基金;

关键词：

RING-OPENING POLYMERIZATION; ACID N-CARBOXYANHYDRIDES; HYPERBRANCHED POLYLYSINE; BLOCK-COPOLYMERS; CONFORMATION; VERSATILE; CELLS; TRANSFECTION; POLYPEPTIDES; STREPTOMYCES;

D O I：

10.1039/c5sc02479j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

epsilon-Poly-lysine (epsilon-PL) is an uncommon cationic, naturally-occurring homopolymer produced by the fermentation process. Due to its significant antimicrobial activity and nontoxicity to humans, epsilon-PL is now industrially produced as an additive, e.g. for food and cosmetics. However, the biosynthetic route can only make polymers with a molecular weight of about 3 kDa. Here, we report a new chemical strategy based on ring-opening polymerization (ROP) to obtain epsilon-PL from lysine. The 2,5-dimethylpyrrole protected alpha-amino-epsilon-caprolactam monomer was prepared through cyclization of lysine followed by protection. ROP of this monomer, followed by the removal of the protecting group, 2,5-dimethylpyrrole, ultimately yielded epsilon-PL with varying molecular weights. The structure of this chemosynthetic epsilon-PL has been fully characterized by H-1 NMR, C-13 NMR, and MALDI-TOF MS analyses. This chemosynthetic epsilon-PL exhibited a similar pK(a) value and low cytotoxicity as the biosynthetic analogue. Using this new chemical strategy involving ROP without the need for phosgene may enable a more cost effective production of epsilon-PL on a larger-scale, facilitating the design of more advanced biomaterials.

引用

页码：6385 / 6391

页数：7

共 49 条

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