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

Overview

Journal Biomolecules

Publisher MDPI

Specialties Biochemistry
Molecular Biology

Date 2024 May 24

PMID 38785949

Authors

Miriam Hollweck

David Jordan

Franz Bracher

Affiliations

Soon will be listed here.

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.

Citing Articles

Characterization of Subcellular Dynamics of Sterol Methyltransferases Clarifies Defective Cell Division in , a C-24 Ethyl Sterol-Deficient Mutant of Arabidopsis.

Ohta D, Fuwa A, Yamaroku Y, Isobe K, Nakamoto M, Okazawa A Biomolecules. 2024; 14(7).

PMID: 39062582 PMC: 11275053. DOI: 10.3390/biom14070868.

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