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海洋环肽stylissamide Ⅰ的全合成研究

陆东涛 刘超 秦路平 邹燕

陆东涛, 刘超, 秦路平, 邹燕. 海洋环肽stylissamide Ⅰ的全合成研究[J]. 药学实践与服务, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
引用本文: 陆东涛, 刘超, 秦路平, 邹燕. 海洋环肽stylissamide Ⅰ的全合成研究[J]. 药学实践与服务, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
Citation: LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011

海洋环肽stylissamide Ⅰ的全合成研究

doi: 10.3969/j.issn.1006-0111.2019.05.011
基金项目: 海军军医大学军事课题(2017JS11)

The total solid synthesis of marine cyclopeptide stylissamide Ⅰ

  • 摘要: 目的 采用固相合成/液相环化方法合成海洋环肽stylissamide Ⅰ。 方法 以2-氯三苯甲基氯树脂(简称二氯树脂)为载体,选用6-氯苯并三氮唑-1,1,3,3-四甲基脲六氟磷酸酯(HCTU)和N,N-二异丙基乙胺(DIPEA)为缩合试剂依次连接9-笏甲氧羰基保护的氨基酸,在三氟乙醇(TFE)的作用下将直链肽从树脂上切割下来,然后使用(3H-1,2,3-三唑并吡啶-3-氧基)三-1-吡咯烷基六氟磷酸盐(PyAOP),N-羟基-7-氮杂苯并三氮唑(HOAt)和N-甲基吗啡啉(NMM)在溶液中完成环合,最后在三氟乙酸(TFA)的处理下脱去侧链保护基,获得环肽粗品。经反相高效液相色谱对所合成的环肽粗品进行纯化,终产物纯度98.9%。通过高分辨质谱、600 MHz 1H-NMR和13C-NMR鉴定,确定所合成环肽为目标环肽。 结果 首次完成海洋环肽stylissamide Ⅰ的全合成,总收率为67%。 结论 此法具有快捷、简便、高效的特点,较好地为stylissamide Ⅰ的固相全合成提供了参考。
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  • [1] 陈炳辰, 王思真, 郭贝贝, 杨峰.  紫杉醇棕榈酸酯的合成及其脂质体的制备与处方研究 . 药学实践与服务, 2024, 42(9): 379-384, 410. doi: 10.12206/j.issn.2097-2024.202404062
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  • 收稿日期:  2018-10-31
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海洋环肽stylissamide Ⅰ的全合成研究

doi: 10.3969/j.issn.1006-0111.2019.05.011
    基金项目:  海军军医大学军事课题(2017JS11)

摘要: 目的 采用固相合成/液相环化方法合成海洋环肽stylissamide Ⅰ。 方法 以2-氯三苯甲基氯树脂(简称二氯树脂)为载体,选用6-氯苯并三氮唑-1,1,3,3-四甲基脲六氟磷酸酯(HCTU)和N,N-二异丙基乙胺(DIPEA)为缩合试剂依次连接9-笏甲氧羰基保护的氨基酸,在三氟乙醇(TFE)的作用下将直链肽从树脂上切割下来,然后使用(3H-1,2,3-三唑并吡啶-3-氧基)三-1-吡咯烷基六氟磷酸盐(PyAOP),N-羟基-7-氮杂苯并三氮唑(HOAt)和N-甲基吗啡啉(NMM)在溶液中完成环合,最后在三氟乙酸(TFA)的处理下脱去侧链保护基,获得环肽粗品。经反相高效液相色谱对所合成的环肽粗品进行纯化,终产物纯度98.9%。通过高分辨质谱、600 MHz 1H-NMR和13C-NMR鉴定,确定所合成环肽为目标环肽。 结果 首次完成海洋环肽stylissamide Ⅰ的全合成,总收率为67%。 结论 此法具有快捷、简便、高效的特点,较好地为stylissamide Ⅰ的固相全合成提供了参考。

English Abstract

陆东涛, 刘超, 秦路平, 邹燕. 海洋环肽stylissamide Ⅰ的全合成研究[J]. 药学实践与服务, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
引用本文: 陆东涛, 刘超, 秦路平, 邹燕. 海洋环肽stylissamide Ⅰ的全合成研究[J]. 药学实践与服务, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
Citation: LU Dongtao, LIU Chao, QIN Luping, ZOU Yan. The total solid synthesis of marine cyclopeptide stylissamide Ⅰ[J]. Journal of Pharmaceutical Practice and Service, 2019, 37(5): 444-449. doi: 10.3969/j.issn.1006-0111.2019.05.011
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