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杀镰孢菌素家族的一个新成员——杀镰孢菌素E的结构解析与合成

A new member of the fusaricidin family - structure elucidation and synthesis of fusaricidin E.

作者信息

Reimann Marcel, Sandjo Louis P, Antelo Luis, Thines Eckhard, Siepe Isabella, Opatz Till

机构信息

Institute of Organic Chemistry, Johannes Gutenberg-University, Duesbergweg 10-14, 55128 Mainz, Germany.

Departamento de Ciências Farmacêuticas, Centro de Ciências da Saúde, Bloco J/K, Universidade Federal de Santa Catarina, Florianópolis 88040-900, SC, Brazil.

出版信息

Beilstein J Org Chem. 2017 Jul 20;13:1430-1438. doi: 10.3762/bjoc.13.140. eCollection 2017.

DOI:10.3762/bjoc.13.140
PMID:28781709
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5530608/
Abstract

Two hitherto unknown fusaricidins were obtained from fermentation broths of three strains. After structure elucidation based on tandem mass spectrometry and NMR spectroscopy, fusaricidin E was synthesized to confirm the structure and the suggested stereochemistry. The synthesis was based on a new strategy which includes an efficient access to the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain from erucamide.

摘要

从三株菌株的发酵液中获得了两种此前未知的镰刀菌素。基于串联质谱和核磁共振光谱对其结构进行解析后，合成了镰刀菌素E以确认结构和所提出的立体化学。该合成基于一种新策略，该策略包括从芥酸酰胺高效获得15-胍基-3-羟基十五烷酰基（GHPD）侧链。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/3b95450ae460/Beilstein_J_Org_Chem-13-1430-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/d0327129ff0e/Beilstein_J_Org_Chem-13-1430-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/6cdc6ce405db/Beilstein_J_Org_Chem-13-1430-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/55b7e97fcef7/Beilstein_J_Org_Chem-13-1430-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/79b575360615/Beilstein_J_Org_Chem-13-1430-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/05d74950793e/Beilstein_J_Org_Chem-13-1430-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/dec984d932d6/Beilstein_J_Org_Chem-13-1430-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/772d8bfbd67a/Beilstein_J_Org_Chem-13-1430-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/f59e891c9850/Beilstein_J_Org_Chem-13-1430-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/3b95450ae460/Beilstein_J_Org_Chem-13-1430-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/d0327129ff0e/Beilstein_J_Org_Chem-13-1430-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/6cdc6ce405db/Beilstein_J_Org_Chem-13-1430-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/55b7e97fcef7/Beilstein_J_Org_Chem-13-1430-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/79b575360615/Beilstein_J_Org_Chem-13-1430-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/05d74950793e/Beilstein_J_Org_Chem-13-1430-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/dec984d932d6/Beilstein_J_Org_Chem-13-1430-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/772d8bfbd67a/Beilstein_J_Org_Chem-13-1430-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/f59e891c9850/Beilstein_J_Org_Chem-13-1430-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/73b1/5530608/3b95450ae460/Beilstein_J_Org_Chem-13-1430-g005.jpg

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