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

doi:10.6023/cjoc201302015

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (08): 1762-1768.DOI: 10.6023/cjoc201302015 Previous Articles Next Articles

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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

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 发布日期:2013-04-12
通讯作者: 谭广慧 E-mail:yenghak@hrbnu.edu.cn;tgh.123@163.com
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.

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

College of Chemistry & Chemical Engineering, Harbin Normal University, Harbin 150025

Received:2013-02-22 Revised:2013-04-03 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).

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

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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]. Chin. J. Org. Chem., 2013, 33(08): 1762-1768.

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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

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

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