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赫苏肽A关键前体的合成

Synthesis of the key precursor of Hirsutellide A.

作者信息

Xu Yanjie, Duan Xuemin, Li Meiling, Jiang Liqin, Zhao Guangle, Meng Yi, Chen Ligong

机构信息

College of Pharmaceuticals and Biotechnology, Tianjin University, Tianjin, 300072, PR China.

出版信息

Molecules. 2005 Jan 31;10(1):259-64. doi: 10.3390/10010259.

DOI:10.3390/10010259
PMID:18007294
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6147622/
Abstract

Hexadepsipeptide 2, the precursor of Hirsutellide A (1), was synthesized in an overall yield of 45% from N-Boc-Me-Gly via three coupling reactions using dicyclohexylcarbodiimide (DCC), O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyl- uronium hexafluorophosphate (HATU) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl), respectively.

摘要

六肽缩酚酸肽2是赫素肽A(1)的前体,以N - Boc - 甲基甘氨酸为原料,通过分别使用二环己基碳二亚胺(DCC)、O-(7-氮杂苯并三唑-1-基)-N,N,N',N'-四甲基脲六氟磷酸盐(HATU)和双(2-氧代-3-恶唑烷基)次膦酰氯(BOP-Cl)的三步偶联反应,以45%的总收率合成得到。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/c2eec9f20196/molecules-10-00259-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/c728d95ef80d/molecules-10-00259-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/bf59883a6b35/molecules-10-00259-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/3179aa014f3f/molecules-10-00259-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/c2eec9f20196/molecules-10-00259-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/c728d95ef80d/molecules-10-00259-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/bf59883a6b35/molecules-10-00259-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/3179aa014f3f/molecules-10-00259-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9b0b/6147622/c2eec9f20196/molecules-10-00259-g004.jpg

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引用本文的文献

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Synthesis and Evaluation of Antimycobacterial and Antiplasmodial Activities of Hirsutellide A and Its Analogues.赫苏肽A及其类似物的抗分枝杆菌和抗疟活性的合成与评价
ACS Omega. 2020 Jun 9;5(24):14451-14460. doi: 10.1021/acsomega.0c01065. eCollection 2020 Jun 23.
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Anthelmintic PF1022A: stepwise solid-phase synthesis of a cyclodepsipeptide containing -methyl amino acids.驱虫剂PF1022A:含α-甲基氨基酸环缩酚酸肽的逐步固相合成
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Cyclodepsipeptides: a rich source of biologically active compounds for drug research.

本文引用的文献

1
Hirsutellide A, a new antimycobacterial cyclohexadepsipeptide from the entomopathogenic fungus Hirsutella kobayasii.赫苏肽A,一种从昆虫病原真菌小林赫苏菌中分离得到的新型抗分枝杆菌环六肽缩酚酸肽。
J Nat Prod. 2002 Sep;65(9):1346-8. doi: 10.1021/np020055+.
环缩酚酸肽:药物研究中生物活性化合物的丰富来源。
Molecules. 2014 Aug 15;19(8):12368-420. doi: 10.3390/molecules190812368.