Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2019 Mar 29:15:811-817.
doi: 10.3762/bjoc.15.78. eCollection 2019.

Synthesis of acylglycerol derivatives by mechanochemistry

Karen J Ardila-Fierro  1 , Andrij Pich  2   3   4 , Marc Spehr  5 , José G Hernández  1 , Carsten Bolm  1
Affiliations

Synthesis of acylglycerol derivatives by mechanochemistry

Karen J Ardila-Fierro et al. Beilstein J Org Chem. .

Abstract

In recent times, many biologically relevant building blocks such as amino acids, peptides, saccharides, nucleotides and nucleosides, etc. have been prepared by mechanochemical synthesis. However, mechanosynthesis of lipids by ball milling techniques has remained essentially unexplored. In this work, a multistep synthetic route to access mono- and diacylglycerol derivatives by mechanochemistry has been realized, including the synthesis of diacylglycerol-coumarin conjugates.

Keywords: ball mill; coumarin; diacylglycerols; lipids; mechanochemistry.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Biologically relevant molecules made, used or derivatized by mechanochemistry.
Figure 2
Figure 2
Isomeric diacyl-sn-glycerols (DAGs).
Scheme 1
Scheme 1
Synthetic route to access protected DAGs; PG = protecting group.
Scheme 2
Scheme 2
Protection of glycidol (1) with TBDMSCl in the ball mill. MM = mixer mill, PBM = planetary ball mill.
Scheme 3
Scheme 3
Cobalt-catalyzed epoxide ring-opening in the ball mill.
Scheme 4
Scheme 4
Mechanosynthesis of DAGs 5.
Scheme 5
Scheme 5
Conjugation of DAG 5a with 7-hydroxycoumarin (9).
Figure 3
Figure 3
UV−vis spectra of DAG 6a (dotted line) and conjugated DAGs 10a and 10a’ as a mixture (10a/10a’ 72:28) in toluene at a concentration of 0.5 μM.
See this image and copyright information in PMC

References

    1. Petridou N I, Spiró Z, Heisenberg C-P. Nat Cell Biol. 2017;19:581–588. doi: 10.1038/ncb3524. - DOI - PubMed
    1. Fritch B, Kosolapov A, Hudson P, Nissley D A, Woodcock H L, Deutsch C, O’Brien E P. J Am Chem Soc. 2018;140:5077–5087. doi: 10.1021/jacs.7b11044. - DOI - PMC - PubMed
    1. Garcia-Manyes S, Beedle A E M. Nat Rev Chem. 2017;1:0083. doi: 10.1038/s41570-017-0083. - DOI
    1. Schönfelder J, Alonso-Caballero A, De Sancho D, Perez-Jimenez R. Chem Soc Rev. 2018;47:3558–3573. doi: 10.1039/c7cs00820a. - DOI - PubMed
    1. Bolm C, Hernández J G. ChemSusChem. 2018;11(9):1410–1420. doi: 10.1002/cssc.201800113. - DOI - PubMed

LinkOut - more resources