Chinese Journal of Organic Chemistry >
Synthesis of Cyclic Ether-N-Benzyl Glycine Polypeptides Based on Single Electron Transfer-Promoted Photocyclization Processes
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).
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.
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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