生物活性环肽Paecilodepsipeptide A的全合成  

Total Synthesis of the Active Cyclodepsipeptides Paecilodepsipeptide A

作　　者：杨明俊[1] 李娟[1] 王永刚[1] 吴婧 张飞[1] 杨中铎[1] 张迎梅[3] 

机构地区：[1]兰州理工大学生命科学与工程学院,甘肃兰州730050 [2]兰州金川新材料科技股份有限公司,甘肃兰州730000 [3]兰州大学生命科学学院,甘肃兰州730000

出　　处：《北京理工大学学报》2013年第7期765-770,共6页Transactions of Beijing Institute of Technology

基　　金：国家自然科学基金资助项目(41261013);甘肃省自然科学研究基金计划项目(0916RJZA007;1212RJYA008);兰州理工大学优秀青年资助计划(1008ZCX007);兰州理工大学教学研究项目(JY2012045)

摘　　要：首次采用逆合成法对昆虫病原真菌Paecilomyces cinnamomeus BCC 9616中分离的高活性抗肿瘤环己肽环肽Paecilodepsipeptide A进行了全合成.采用标准肽化学合成方法,完成了五肽的合成;以酪氨酸甲酯盐酸盐为起始原料,得到O-异戊烯基-D-酪氨酸衍生物;通过五肽与O-异戊烯基-D-酪氨酸衍生物的酯化反应得到环化前体;采取大环内酰氨化和大环内酯化的策略进行关环,完成了天然产物Paecilodepsipeptide A的全合成,产率72%.目标化合物经质谱与核磁共振光谱结构确证与天然产物一致.Paecilodepsipeptide A isolated from Paecilomyces cinnamorneus BCC 9616 was first synthesized by retrosynthesis method, which shows good antimalarial and antitumor activity. Pentapeptide was synthesized by standard peptide synthesis method at first. Then, O- isopentenyl-D-tyrosine derivatives were obtained by using tyrosine methyl ester hydrochloride as the raw material. The cyclization precursors were obtained by esterification reaction between the pentapeptide and the O-isopentenyl-D-tyrosine derivatives. Finally, the cyclization was achieved and the yield rate of Paecilodepsipeptide A was 72 %. The structures of the synthesized product were identified by 1H NMR and 13C NMR spectra, which is identical to the natural product.

关 键 词：Paecilodepsipeptide A 环肽 全合成 

分 类 号：O621.3[理学—有机化学]