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亲电天然产物的固相富集与分析

Solid-phase enrichment and analysis of electrophilic natural products.

作者信息

Wesche Frank, He Yue, Bode Helge B

机构信息

Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue-Strasse 9, D-60438 Frankfurt am Main, Germany.

Merck Stiftungsprofessur für Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue-Strasse 9, D-60438 Frankfurt am Main, Germany; Buchmann Institute for Molecular Life Sciences (BMLS), Goethe Universität Frankfurt, Max-von-Laue-Strasse 15, D-60438 Frankfurt am Main, Germany.

出版信息

Beilstein J Org Chem. 2017 Mar 2;13:405-409. doi: 10.3762/bjoc.13.43. eCollection 2017.

DOI:10.3762/bjoc.13.43
PMID:28382178
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5355884/
Abstract

In search for new natural products, which may lead to the development of new drugs for all kind of applications, novel methods are needed. Here we describe the identification of electrophilic natural products in crude extracts via their reactivity against azide as a nucleophile followed by their subsequent enrichment using a cleavable azide-reactive resin (CARR). Using this approach, natural products carrying epoxides and α,β-unsaturated enones as well as several unknown compounds were identified in crude extracts from entomopathogenic bacteria.

摘要

为了寻找可能会带来适用于各种用途的新药的新型天然产物,需要新的方法。在此,我们描述了通过粗提物中亲电天然产物与作为亲核试剂的叠氮化物的反应性来鉴定它们,随后使用可裂解的叠氮化物反应树脂(CARR)对其进行富集。利用这种方法,在昆虫病原细菌的粗提物中鉴定出了带有环氧化物和α,β-不饱和烯酮的天然产物以及几种未知化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2bd1/5355884/f9433727b889/Beilstein_J_Org_Chem-13-405-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2bd1/5355884/084dfb335cd7/Beilstein_J_Org_Chem-13-405-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2bd1/5355884/558b65cbef55/Beilstein_J_Org_Chem-13-405-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2bd1/5355884/f9433727b889/Beilstein_J_Org_Chem-13-405-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2bd1/5355884/084dfb335cd7/Beilstein_J_Org_Chem-13-405-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2bd1/5355884/558b65cbef55/Beilstein_J_Org_Chem-13-405-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2bd1/5355884/f9433727b889/Beilstein_J_Org_Chem-13-405-g004.jpg

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Chemical assay-guided natural product isolation solid-supported chemodosimetric fluorescent probe.
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ACS Chem Biol. 2016 Aug 19;11(8):2328-36. doi: 10.1021/acschembio.5b00924. Epub 2016 Jun 28.
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Solid-Phase Enrichment and Analysis of Azide-Labeled Natural Products: Fishing Downstream of Biochemical Pathways.叠氮标记天然产物的固相富集与分析:生化途径下游的探寻
Chemistry. 2016 Jan 11;22(2):639-45. doi: 10.1002/chem.201503781. Epub 2015 Dec 2.
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