Chemo‐Enzymatic Synthesis of Mixed Docosahexaenoic Acid Phosphatidylcholine Conjugates
Abstract: Docosahexaenoic acid (DHA, C22: 6 n‐3) is a critical omega‐3 polyunsaturated fatty acid (PUFA) with essential roles in brain and retinal functions. Its selective uptake into these tissues is mediated by several pathways, including the transporter Mfsd2a, which preferentially utilizes lysophosphatidylcholine‐DHA (LPC‐DHA) as a substrate. Due to the low de novo synthesis of DHA, optimizing its dietary intake and exploring novel delivery strategies are important in pathologies that affect PUFA proportion. The present work focuses on developing an efficient chemo‐enzymatic methodology to access structured mixed DHA phosphatidylcholines (mixed DHA‐PCs), valuable biological tools for enhancing drug and/or DHA delivery to the brain and retina. Chemo‐enzymatic methods were established to synthesize mixed sn1‐ or sn2‐DHA‐PC isomers, to study the importance of DHA position, from cost‐effective glycerophosphorylcholine (GPC). The approach aligns with green chemistry principles by leveraging lipase‐catalyzed regioselective acylation and deacylation reactions, thus reducing the number of chemical steps compared to traditional methods. The resulting mixed PCs AceDoPC®, DoAcePC (stabilized forms of LPC‐DHA), and phenolic‐DHA‐PCs were produced at a scale suitable for future in vivo studies, enabling investigations into the positional effect of DHA on brain and retinal uptake.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Chemo‐Enzymatic Synthesis of Mixed Docosahexaenoic Acid Phosphatidylcholine Conjugates ; day:05 ; month:03 ; year:2025 ; extent:10
European journal of organic chemistry ; (05.03.2025) (gesamt 10)
- Creator
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Lehoux, Jordan
Grosjean, Felix
Lobo, Alexandre
Lagarde, Michel
Bernoud‐Hubac, Nathalie
Durand, Thierry
Crauste, Celine
- DOI
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10.1002/ejoc.202500083
- URN
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urn:nbn:de:101:1-2503061313334.951605173368
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:25 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Lehoux, Jordan
- Grosjean, Felix
- Lobo, Alexandre
- Lagarde, Michel
- Bernoud‐Hubac, Nathalie
- Durand, Thierry
- Crauste, Celine
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