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吡咯并喹喔啉 A-D 的非生物合成与研究。

Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D.

机构信息

Department of Chemistry and Biochemistry , University of California, Santa Cruz , Santa Cruz , California 95064 , United States.

出版信息

Org Lett. 2020 Feb 21;22(4):1516-1519. doi: 10.1021/acs.orglett.0c00098. Epub 2020 Feb 4.

DOI:10.1021/acs.orglett.0c00098
PMID:32017580
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7864527/
Abstract

Pyonitrins A-D are recently isolated natural products from the insect-associated strain, which were isolated from complex fractions that exhibited antifungal activity via an murine candidiasis assay. Genomic studies of suggested that pyonitrins A-D are formed via a spontaneous nonenzymatic reaction between biosynthetic intermediates of two well-known natural products pyochelin and pyrrolnitrin. Herein we have accomplished the first biomimetic total synthesis of pyonitrins A-D in three steps and studied the nonenzymatic formation of the pyonitrins using N NMR spectroscopy.

摘要

吡咯并[1,2-a]吡啶-2,3-二酮 A-D 是从昆虫共生的菌株中分离得到的天然产物，这些化合物是从具有抗真菌活性的复杂混合物中分离得到的，其活性通过小鼠念珠菌病模型检测。对菌株的基因组研究表明，吡咯并[1,2-a]吡啶-2,3-二酮 A-D 是通过两种著名天然产物吡咯并[1,2-a]吡啶-2,3-二酮和吡咯并[1,2-a]吡啶-3,4-二酮生物合成中间体之间的自发非酶反应形成的。本文我们通过三步反应首次实现了吡咯并[1,2-a]吡啶-2,3-二酮 A-D 的全生物模拟合成，并通过 N NMR 光谱研究了吡咯并[1,2-a]吡啶-2,3-二酮的非酶形成过程。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/75d6d6462a0b/ol0c00098_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/49af00660de2/ol0c00098_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/00996b7b379c/ol0c00098_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/083bb0cd2516/ol0c00098_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/b4c7a39cef60/ol0c00098_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/b9358140128c/ol0c00098_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/75d6d6462a0b/ol0c00098_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/49af00660de2/ol0c00098_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/00996b7b379c/ol0c00098_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/083bb0cd2516/ol0c00098_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/b4c7a39cef60/ol0c00098_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/b9358140128c/ol0c00098_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d780/7864527/75d6d6462a0b/ol0c00098_0004.jpg

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