ePrints

Unlocking nature's antioxidants: a novel method for synthesising plasmalogens

Lookup NU author(s): Dr Jay Tromans, Dr Bian Zhang, Emeritus Professor Bernard Golding

Downloads

• Published version [.pdf]

Licence

This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

© 2024 The Royal Society of ChemistryPlasmalogens are glycerophospholipids distinguished by their O-(Z)-vinyl ether at the sn-1 position. These lipids are implicated in several disease states requiring analytical, diagnostic and therapeutic interventions, which demand synthetic availability for a variety of structural types. By deploying the new O-protecting group 1,4-dimethoxynaphthyl-2-methyl (‘DIMON’) and a new stereospecific method for accessing Z-vinyl ethers, a reproducible, versatile synthetic route to plasmalogens [plasmenyl phosphocholines] has been developed. A key intermediate is (S,Z)-1-((1,4-dimethoxynaphthalen-2-yl)methoxy)-3-(hexadec-1-en-1-yloxy)propan-2-ol, which in principle, permits plasmalogen synthesis ‘à la carte’ at scale. The methodology compares favourably with all previous synthetic routes by virtue of the very high configurational (>99% Z) and optical purity (>99% ee), including the ability to incorporate polyunsaturated fatty acyl chains (e.g. all Z docosahexaenoic acid) reliably at the sn-2 position.

Publication metadata

Author(s): Tromans J, Zhang B, Golding BT

Publication type: Article

Publication status: Published

Journal: Organic and Biomolecular Chemistry

Year: 2024

Volume: 22

Issue: 39

Pages: 7989-7995

Online publication date: 05/09/2024

Acceptance date: 27/08/2024

Date deposited: 16/09/2024

ISSN (print): 1477-0520

ISSN (electronic): 1477-0539

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/D4OB01233J

DOI: 10.1039/d4ob01233j

Data Access Statement: All data reported in this paper is available on request from the corresponding author.

Altmetrics

Share