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Synthesis of a Side Chain Alkyne Analogue of Sitosterol as a Chemical Probe for Imaging in Plant Cells

Authors :
Miriam Hollweck
David Jordan
Franz Bracher
Source :
Biomolecules, Vol 14, Iss 5, p 542 (2024)
Publication Year :
2024
Publisher :
MDPI AG, 2024.

Abstract

Clickable chemical tools are essential for studying the localization and role of biomolecules in living cells. For this purpose, alkyne-based close analogs of the respective biomolecules are of outstanding interest. Here, in the field of phytosterols, we present the first alkyne derivative of sitosterol, which fulfills the crucial requirements for such a chemical tool as follows: very similar in size and lipophilicity to the plant phytosterols, and correct absolute configuration at C-24. The alkyne sitosterol FB-DJ-1 was synthesized, starting from stigmasterol, which comprised nine steps, utilizing a novel alkyne activation method, a Johnson–Claisen rearrangement for the stereoselective construction of a branched sterol side chain, and a Bestmann–Ohira reaction for the generation of the alkyne moiety.

Details

Language :
English
ISSN :
2218273X
Volume :
14
Issue :
5
Database :
Directory of Open Access Journals
Journal :
Biomolecules
Publication Type :
Academic Journal
Accession number :
edsdoj.66c35d9cb9a42ac8b28c2ffd0111e50
Document Type :
article
Full Text :
https://doi.org/10.3390/biom14050542