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Updated: Apr 30, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Casuarine stereoisomers from achiral substrates: chemoenzymatic synthesis and inhibitory properties
Alda Lisa Concia1, Livia Gómez, Teodor Parella
1Biotransformation and Bioactive Molecules Group, Departamento de Química Biológica y Modelización Molecular, Instituto de Química Avanzada de Cataluña, IQAC-CSIC , Jordi Girona 18-26, 08034 Barcelona, Spain.
Abstract:
A straightforward chemoenzymatic synthesis of four uncovered casuarine stereoisomers is described. The strategy consists of L-fuculose-1-phosphate aldolase F131A-variant-catalyzed aldol addition of dihydroxyacetone phosphate to aldehyde derivatives of 1,4-dideoxy-1,4-imino-D-arabinitol (DAB) and its enantiomer (LAB) and subsequent one-pot catalytic deprotection-reductive amination. DAB and LAB were obtained from dihydroxyacetone and aminoethanol using D-fructose-6-phosphate aldolase and L-rhamnulose-1-phosphate aldolase catalysts, respectively. The new ent-3-epi-casuarine is a strong inhibitor of α-d-glucosidase from rice and of rat intestinal sucrase.
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