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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
【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.
【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;
- 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2013年08期
- 【分类号】O631.3
- 【被引频次】1
- 【下载频次】67