基于Ugi多组分反应的赖氨酸与糠醛的直接聚合

陶月; 陈金龙; 王士学; 陶友华

doi:10.11777/j.issn1000-3304.2020.20025

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基于Ugi多组分反应的赖氨酸与糠醛的直接聚合

论文 | 更新时间：2021-01-26

- 基于Ugi多组分反应的赖氨酸与糠醛的直接聚合
- Direct Polymerization of Lysine and Furfural via Ugi Reaction
- 高分子学报 2020年51卷第7期页码：738-743
- 作者机构：
  
  1.中国科学院长春应用化学研究所中国科学院生态环境高分子材料重点实验室　长春 130022
  2.中国科学技术大学应用化学与工程学院　合肥 230026
- 作者简介：
  
  E-mail: youhua.tao@ciac.ac.cn You-hua Tao, E-mail: youhua.tao@ciac.ac.cn
- 基金信息：
  
  国家自然科学基金(基金号 91856113，51873211)资助项目
- DOI：10.11777/j.issn1000-3304.2020.20025
  中图分类号：
- 纸质出版日期：2020-7，
  
  网络出版日期：2020-4-16，
  
  收稿日期：2020-2-8，
  
  修回日期：2020-2-27，
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陶月, 陈金龙, 王士学, 陶友华. 基于Ugi多组分反应的赖氨酸与糠醛的直接聚合[J]. 高分子学报, 2020,51(7):738-743.

Yue Tao, Jin-long Chen, Shi-xue Wang, You-hua Tao. Direct Polymerization of Lysine and Furfural via Ugi Reaction[J]. Acta Polymerica Sinica, 2020,51(7):738-743.
陶月, 陈金龙, 王士学, 陶友华. 基于Ugi多组分反应的赖氨酸与糠醛的直接聚合[J]. 高分子学报, 2020,51(7):738-743. DOI： 10.11777/j.issn1000-3304.2020.20025.

Yue Tao, Jin-long Chen, Shi-xue Wang, You-hua Tao. Direct Polymerization of Lysine and Furfural via Ugi Reaction[J]. Acta Polymerica Sinica, 2020,51(7):738-743. DOI： 10.11777/j.issn1000-3304.2020.20025.

摘要

报道了基于Ugi多组分反应的

-叔丁氧羰基-

-赖氨酸、糠醛与叔丁基异腈的聚合. 聚合条件温和，无需使用催化剂，且所得聚合物的相对数均分子量

最高可达10.0 kg/mol. 特别是，聚合在水中也可顺利进行，可以避免有毒溶剂的使用，符合绿色化学发展理念. 核磁共振氢谱(

H-NMR)、核磁共振碳谱(

C-NMR)及基质辅助激光解吸电离飞行时间质谱(MALDI-TOF-MS)的结果证实所得聚合物具有类肽的结构. 在此基础上，推测

-叔丁氧羰基-

-赖氨酸、糠醛与叔丁基异腈的聚合符合Ugi反应的一般机理，即糠醛首先与氨基缩合形成亚胺，再经过两次的亲核加成、Mumm重排以及酰基转移反应，最终形成具有类肽结构的聚合物. DSC测试结果表明聚合物玻璃化转变温度(

)为116 °C，无明显熔点. 所获得的聚合物在生物降解材料及生物医用材料等领域具有潜在的应用价值，这为赖氨酸和糠醛的直接聚合以及可再生资源的高附加值利用开辟了一条新路径.

Abstract

Lysine and furfural are naturally available renewable resources. With the dwindling petroleum and eventual depletion of fossil resources

the controlled synthesis of bio-based polymers derived from lysine and furfural has recently become a growing research focus. However

their simple and general polymerization still remains a key challenge. Herein

we demonstrate that natural lysine and furfural monomers can be polymerized

via

Ugi reaction in a step-growth fashion

which leads to the polypeptoids with a number average molecular weight (

) up to 10.0 kg/mol

under mild conditions (open to air

room temperature

and catalyst free). More importantly

the polymerization can be carried out in water

avoiding the use of toxic solvents. The structures of resultant polypeptoids were confirmed by

H- and

C-NMR spectroscopy. All of the signals attributed to the repeating unit of the polypeptoid that should be produced by the Ugi reaction are visible. Moreover

the MALDI-TOF MS analysis of the resulting product consists of an array of peaks separated by a 407.2 Da interval

which corresponds to the molar masses of the repeating unit. The MALDI-TOF MS result is consistent with the proposed mechanism of Ugi reaction. These polypeptoids exhibit a

value of 116 °C

and do not show melting transition. Indeed

the renewable feedstocks and simple concepts described here offer an attractive framework from which the Ugi reaction can be applied to prepare lysine and furfural based polymers.

关键词

Ugi多组分反应赖氨酸糠醛可再生资源

Keywords

Ugi reactionLysineFurfuralRenewable resource

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