Chemoproteomic Evaluation of the Polyacetylene Callyspongynic Acid
File(s)
Accepted version
Author(s)
Type
Journal Article
Abstract
Polyacetylenes are a class of alkyne-containing natural products. Although potent bioactivities and thus possible applications as chemical probes have already been reported for some polyacetylenes, insights into the biological activities or molecular mode of action are still rather limited in most cases. To overcome this limitation, we describe the application of the polyacetylene callyspongynic acid in the development of an experimental roadmap for characterizing potential protein targets of alkyne-containing natural products. To this end, we undertook the first chemical synthesis of callyspongynic acid. We then used in situ chemical proteomics methods to demonstrate extensive callyspongynic acid-mediated chemical tagging of endoplasmic reticulum-associated lipid-metabolizing and modifying enzymes. We anticipate that an elucidation of protein targets of natural products may serve as an effective guide to the development of subsequent biological assays that aim to identify chemical phenotypes and bioactivities.
Date Issued
2015-07-14
Date Acceptance
2015-03-09
Citation
Chemistry-A European Journal, 2015, 21 (30), pp.10721-10728
ISSN
1521-3765
Publisher
Wiley-VCH Verlag
Start Page
10721
End Page
10728
Journal / Book Title
Chemistry-A European Journal
Volume
21
Issue
30
Copyright Statement
This is the peer reviewed version of the following article: Nickel, S., Serwa, R. A., Kaschani, F., Ninck, S., Zweerink, S., Tate, E. W. and Kaiser, M. (2015), Chemoproteomic Evaluation of the Polyacetylene Callyspongynic Acid. Chem. Eur. J., 21: 10721–10728., which has been published in final form at https://dx.doi.org/10.1002/chem.201500934. This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
alkynes
click chemistry
drug discovery
natural products
proteomics
1ST TOTAL-SYNTHESIS
CLICK CHEMISTRY
CHEMICAL PROTEOMICS
PROTEIN LIPIDATION
NATURAL-PRODUCTS
FATTY ALDEHYDE
HUMAN-CELLS
ALPHA
BIOLOGY
ENZYME
Publication Status
Published