title: Aldolase-catalyzed synthesis of conformationally constrained iminocyclitols: preparation of polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines.
abstract: A straightforward chemo-enzymatic synthesis of new polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines is developed. The two-step strategy consists of l-fuculose-1-phosphate aldolase variant F131A-catalyzed aldol addition of dihydroxyacetone phosphate to rac-N-benzyloxycarbonylindoline-2-carbaldehyde as well as (2S*,3aS*,7aS*)- and (2S*,3aR*,7aR*)-N-benzyloxycarbonyloctahydroindole-2-carbaldehydes and a subsequent one-step catalytic deprotection-reductive amination.
authors.affiliation: Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC , 50009 Zaragoza, Spain.
authors.forename: Pedro
authors.initials: P
authors.lastname: Laborda
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Sayago
authors.forename: Carlos
authors.initials: C
authors.lastname: Cativiela
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 / Q000378:metabolism; D000447:Aldehydes / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D054812:Cyclitols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004099:Dihydroxyacetone Phosphate / Q000737:chemistry; D005634:Fructose-Bisphosphate Aldolase / Q000378:metabolism*; D006026:Glycoside Hydrolases / Q000378:metabolism; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D054812:Cyclitols; D006575:Heterocyclic Compounds, 3-Ring; D004099:Dihydroxyacetone Phosphate; C116609:3-hydroxybutanal; D006026:Glycoside Hydrolases; D000446:Aldehyde-Lyases; D005634:Fructose-Bisphosphate Aldolase; C036027:L-fuculosephosphate aldolase