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Updated: Jun 6, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
An efficient synthesis of γ-hydroxy-α,β-unsaturated aldehydic esters of 2-lysophosphatidylcholine
Jaewoo Choi1, James M Laird, Robert G Salomon
1Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106-7078, United States.
Abstract:
The diverse biological activities of γ-hydroxyalkenal phospholipids and their involvement in disease are the subject of intense study. Phospholipid aldehydes, such as the 4-hydroxy-7-oxohept-5-enoic acid ester of 2-lyso-phosphatidylcholine (HOHA-PC), the 5-hydroxy-8-oxo-6-octenoic acid ester of 2-lyso-PC (HOOA-PC), and the 9-hydroxy-12-oxododec-10-enoic acid ester of 2-lyso-PC (HODA-PC), are generated by oxidative cleavage of polyunsaturated fatty acyl phospholipids. To facilitate investigations of their chemistry and biology, we now report efficient total synthesis of HOOA, HODA, and HOHA phospholipids. Because the target γ-hydroxyalkenals readily decompose through oxidation of the aldehyde group to a carboxylic acid or through cyclization to furans, these synthesis generate the sensitive functional array of the target phospholipids under mild conditions from acetal derivatives that are suitable for long-term storage.
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