title: Casuarine stereoisomers from achiral substrates: chemoenzymatic synthesis and inhibitory properties.
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.
authors.affiliation: Biotransformation 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.
authors.forename: Alda Lisa
authors.initials: AL
authors.lastname: Concia
authors.forename: Livia
authors.initials: L
authors.lastname: Gómez
authors.forename: Teodor
authors.initials: T
authors.lastname: Parella
authors.forename: Jesús
authors.initials: J
authors.lastname: Joglar
authors.forename: Pere
authors.initials: P
authors.lastname: Clapés
mesh_terms: D000446:Aldehyde-Lyases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001089:Arabinose / Q000737:chemistry*; D004099:Dihydroxyacetone Phosphate / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D019856:Ethanolamine / Q000737:chemistry*; D005634:Fructose-Bisphosphate Aldolase / Q000037:antagonists & inhibitors* / Q000737:chemistry; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D050113:Imino Furanoses / Q000737:chemistry*; D015394:Molecular Structure; D012275:Oryza / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D013237:Stereoisomerism; D013393:Sucrase / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D013402:Sugar Alcohols / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D050113:Imino Furanoses; D011758:Pyrroles; D013402:Sugar Alcohols; C409108:casuarine; C058137:1,4-dideoxy-1,4-iminoarabinitol; D004099:Dihydroxyacetone Phosphate; D019856:Ethanolamine; D001089:Arabinose; D013393:Sucrase; D000446:Aldehyde-Lyases; D005634:Fructose-Bisphosphate Aldolase; C036027:L-fuculosephosphate aldolase; C022526:rhamnulose-1-phosphate adolase