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2013 , Vol. 33 >Issue 08: 1762 - 1768

DOI: https://doi.org/10.6023/cjoc201302015

研究论文

基于光诱导单电子转移反应历程合成醚-聚N-苄基甘氨酸肽环化物

  • 粱波颖 ,
  • 金英学 ,
  • 于沙沙 ,
  • 曲凤玉 ,
  • 谭广慧
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  • 哈尔滨师范大学化学化工学院 哈尔滨 150025

收稿日期: 2013-02-22

  修回日期: 2013-04-03

  网络出版日期: 2013-04-12

基金资助

国家自然科学基金(Nos. 20972036, 21272048);黑龙江省自然科学基金(No. B20913);黑龙江省高效科技创新团队建设计划(No. 2011TD010)资助项目.

收起

Synthesis of Cyclic Ether-N-Benzyl Glycine Polypeptides Based on Single Electron Transfer-Promoted Photocyclization Processes

  • Liang Boying ,
  • Jin Yingxue ,
  • Yu Shasha ,
  • Qu Fengyu ,
  • Tan Guanghui
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  • College of Chemistry & Chemical Engineering, Harbin Normal University, Harbin 150025

Received date: 2013-02-22

  Revised date: 2013-04-03

  Online published: 2013-04-12

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20972036, 21272048), the Natural Science Foundation of Heilongjiang Province (No. B20913), and the Program for Scientific Technological Innovation Team Construction in Universites of Heilongjiang Province (No. 211TD010).

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摘要

研究了以邻苯二甲酰亚胺为电子受体, 以末端三甲基硅烷基的醚-聚N-苄基甘氨酸肽链为电子给体的化合物5a～5f的光反应, 发展了新的合成环肽类化合物的方法. 末端三甲基硅烷基的醚-聚N-苄基甘氨酸肽链——邻苯二甲酰亚胺5a～5f在甲醇溶剂中进行光反应, 经连续的单电子转移(SET)历程有效地合成了环肽类化合物6a～6f. 所合成的环肽类化合物的结构经核磁共振谱、高分辨质谱、X光晶体衍射所确定.

关键词： 单电子转移(SET); 光环化; 环肽; 邻苯二甲酰亚胺; N-三甲基硅烷基甲基肽电子给体

本文引用格式

粱波颖 , 金英学 , 于沙沙 , 曲凤玉 , 谭广慧 . 基于光诱导单电子转移反应历程合成醚-聚N-苄基甘氨酸肽环化物[J]. 有机化学, 2013 , 33(08) : 1762 -1768 . DOI: 10.6023/cjoc201302015

Abstract

Exploratory photochemical studies on trimethylsilyl-terminated phthalimide-ether-N-benzylpolyglycines in which phthalimides worked as light absorbance acceptors and ether-N-(trimethylsilyl)methylamides served as electron donor centers have been conducted, leading to the development of new synthetic methodology to construct cyclic polypeptide mimetics. It was found that irradiation on trimethylsilyl-terminated phthalimide-ether-poly-N-benzylglycine 5a～5f in methanol led to efficient generation of cyclic peptide products 6a～6f, which may be through sequential single electron transfer (SET) pathway. The structures of these cyclic peptide products were determined by NMR and HRMS spectroscopy as well as fully characterized by X-ray crystallography.

Key words： single electron transfer (SET); photoyclization; cyclic peptide; phthalimide; N-trimethylsilylmethyl peptide electron donor

参考文献

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