Articles

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).

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 5a5f in methanol led to efficient generation of cyclic peptide products 6a6f, 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.

Cite this article

Liang Boying , Jin Yingxue , Yu Shasha , Qu Fengyu , Tan Guanghui . Synthesis of Cyclic Ether-N-Benzyl Glycine Polypeptides Based on Single Electron Transfer-Promoted Photocyclization Processes[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1762 -1768 . DOI: 10.6023/cjoc201302015

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