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l-β-(6-薁基)丙氨酸与荧光肌动蛋白破坏剂(6-薁基)松弛素H的合成。

Synthesis of l-β-(6-azulenyl)alanine and the fluorescent actin disruptor (6-azuleno)chalasin H.

作者信息

Hauser Maurice, Schmidt Katharina, Beiderwieden Leonard, Yi Cheng, Gerdes Kjeld, Kalesse Markus, Gerke Jennifer, Stradal Theresia E, Cox Russell J

机构信息

Institute for Organic Chemistry and BMWZ, Leibniz University of Hannover Schneiderberg 38 30167 Hannover Germany

Department of Cell Biology, Helmholtz Centre for Infection Research Inhoffenstraße 7 38124 Braunschweig Germany.

出版信息

RSC Adv. 2025 Jul 22;15(32):26048-26051. doi: 10.1039/d5ra04702a. eCollection 2025 Jul 21.

DOI:10.1039/d5ra04702a
PMID:40697474
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12281303/
Abstract

l-β-(6-Azulenyl)alanine was synthesised for the first time. Supplementation of this compound to Δ led to the biosynthesis of the unnatural (6-azuleno)chalasin H and its 1'-bromo congener that have unprecedented natural product skeletons and that are both fluorescent and highly cytotoxic, with IC of 0.18 μg mL L929 cells . Actin staining showed that both compounds are potent, but partially reversible, actin disruptors.

摘要

首次合成了l-β-(6-薁基)丙氨酸。向Δ中添加该化合物导致了非天然(6-薁基)杀稻瘟菌素H及其1'-溴同类物的生物合成，它们具有前所未有的天然产物骨架，且兼具荧光性和高细胞毒性，对L929细胞的IC为0.18 μg/mL。肌动蛋白染色表明这两种化合物都是有效的，但部分可逆的肌动蛋白破坏剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/647eb45ef29a/d5ra04702a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/a5cc0e35d6fc/d5ra04702a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/9eb371ecc663/d5ra04702a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/0306c1b3784b/d5ra04702a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/647eb45ef29a/d5ra04702a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/a5cc0e35d6fc/d5ra04702a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/9eb371ecc663/d5ra04702a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/0306c1b3784b/d5ra04702a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6e07/12281303/647eb45ef29a/d5ra04702a-f1.jpg

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