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Updated: Jul 2, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Δ-Keto-acid/hydroxy-lactone isomerization in some lichen depsides, depsidones and diphenyl ethers
Philippe Uriac1, Solenn Ferron1, Philippe Jehan2
1Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, Rennes, France. sophie.tomasi@univ-rennes.fr.
Abstract:
In some compounds in lichens, the carboxylic acid is ortho-substituted by an 2-oxoalkyl chain. This particular structure induces the existence of δ-keto-acid ka or hydroxy-lactone hl isomers, clearly identified by their NMR data and chemical properties, such as dehydration, methylation and behaviour in thermal conditions. Internal hydrogen bonding between the carboxylic acid and substituent in the ortho' position is proposed as an isomerization modulator: an H-bond acceptor (OCH3) leads to ka isomers, whereas hl isomers are obtained with an H-bond donor (OH).
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