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生物活性环二肽天然产物合成的案例研究。

Case studies of the synthesis of bioactive cyclodepsipeptide natural products.

机构信息

Zentrum für Medizinische Biotechnologie, Fakultät für Biologie, Universitätsstraße 2, 45117 Essen, Germany.

出版信息

Molecules. 2013 Jan 24;18(2):1337-67. doi: 10.3390/molecules18021337.

DOI:10.3390/molecules18021337
PMID:23348990
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6270203/
Abstract

Cyclodepsipeptide natural products often display intriguing biological activities that along with their complex molecular scaffolds, makes them interesting targets for chemical synthesis. Although cyclodepsipeptides feature highly diverse chemical structures, their synthesis is often associated with similar synthetic challenges such as the establishment of a suitable macrocyclization methodology. This review therefore compiles case studies of synthetic approaches to different bioactive cyclodepsipeptide natural products, thereby illustrating obstacles of cyclodepsipeptide synthesis as well as their overcomings.

摘要

环二肽天然产物通常具有有趣的生物活性,其复杂的分子骨架使它们成为化学合成的有趣目标。虽然环二肽具有高度多样化的化学结构,但它们的合成通常涉及类似的合成挑战,例如建立合适的大环化方法。因此,本综述汇编了不同生物活性环二肽天然产物的合成方法案例研究,从而说明了环二肽合成的障碍及其克服方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/c6aad2ca5cc8/molecules-18-01337-sch021.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/b8bd2e0892bc/molecules-18-01337-sch003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/f583a1252f69/molecules-18-01337-sch005.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/e6ae8b2a70d0/molecules-18-01337-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/ece8566b14ea/molecules-18-01337-sch007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/d301e1a11a22/molecules-18-01337-sch008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/064b418fbdc3/molecules-18-01337-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/807ba71e753e/molecules-18-01337-sch009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/66d3ee5fd0b3/molecules-18-01337-sch010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/47343c0d555e/molecules-18-01337-sch011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/ebe8352f55b7/molecules-18-01337-sch012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/35904f68136f/molecules-18-01337-sch013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/29fb212a9fac/molecules-18-01337-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/9a5fe8c189e7/molecules-18-01337-sch014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/e559602a06e1/molecules-18-01337-sch015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/3da5cd2d4815/molecules-18-01337-sch016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/61e37d4b6ba6/molecules-18-01337-sch017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/4b24c55be967/molecules-18-01337-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/a64c46f225c7/molecules-18-01337-sch018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/4aa1d134c8f6/molecules-18-01337-sch019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/3935456612ab/molecules-18-01337-sch020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3841/6270203/c6aad2ca5cc8/molecules-18-01337-sch021.jpg

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ACS Med Chem Lett. 2011 Nov 10;2(11):861-865. doi: 10.1021/ml200176m. Epub 2011 Aug 31.
3
Synthetic routes and biological evaluation of largazole and its analogues as potent histone deacetylase inhibitors.
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Front Microbiol. 2023 Oct 2;14:1276928. doi: 10.3389/fmicb.2023.1276928. eCollection 2023.
4
Total Synthesis of the Cyclic Depsipeptide Vioprolide D via its (Z)-Diastereoisomer.通过其(Z)-非对映异构体全合成环状二肽 Vioprolide D。
Angew Chem Int Ed Engl. 2020 Jul 20;59(30):12357-12361. doi: 10.1002/anie.202002328. Epub 2020 Apr 20.
5
Cyclodepsipeptides: a rich source of biologically active compounds for drug research.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.
largazole 及其类似物作为有效的组蛋白去乙酰化酶抑制剂的合成路线和生物评价。
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4
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Chem Rev. 2011 May 11;111(5):3208-35. doi: 10.1021/cr100187n. Epub 2011 Apr 11.
5
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Org Biomol Chem. 2011 May 21;9(10):3825-33. doi: 10.1039/c0ob01169j. Epub 2011 Mar 29.
6
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7
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