Bibliographic Details
| Title: |
Synthesis of Enantiostructured Triacylglycerol Prodrugs Constituting an Active Drug Located at Terminal sn -1 and sn -3 Positions of the Glycerol Backbone. |
| Authors: |
Jónsdottir, Lena Rós1 (AUTHOR), Haraldsson, Gudmundur G.1 (AUTHOR) gghar@hi.is |
| Source: |
Molecules. Mar2025, Vol. 30 Issue 5, p991-1. 23p. |
| Subject Terms: |
*OMEGA-3 fatty acids, *ASYMMETRIC synthesis, *BENZYL ethers, *LIPASES, *PRODRUGS |
| Abstract: |
The current paper reports the asymmetric synthesis of a focused library of enantiostructured triacylglycerols (TAGs) constituting a potent drug of the NSAID type (ibuprofen or naproxen) along with a pure bioactive n-3 polyunsaturated fatty acid (PUFA) intended as a novel type of prodrug. In this second category, a TAG prodrug of the terminal sn-1 or sn-3 position of the glycerol skeleton is acylated with a single saturated medium-chain fatty acid (C6, C8, C10, or C12), and another with the drug entity; the PUFA (EPA or DHA) is located in the sn-2 position. This was accomplished by a six-step chemoenzymatic approach, two of which were promoted by a lipase, starting from enantiopure (R)- and (S)-solketals. The highly regioselective immobilized Candida antarctica lipase (CAL-B) played a crucial role in the regiocontrol of the synthesis. The most challenging key step involved the incorporation of the drugs that were activated as oxime esters by the lipase exclusively in the terminal position of glycerol that is protected as a benzyl ether. All combinations, a total of 32 such prodrug TAGs, were prepared, isolated, and fully characterized, along with 24 acylglycerol intermediates, obtained in very-high-to-excellent yields in the majority of cases. [ABSTRACT FROM AUTHOR] |
|
Copyright of Molecules is the property of MDPI and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) |
| Database: |
Academic Search Complete |
|
Full text is not displayed to guests. |
Login for full access.
|
