info:eu-repo/semantics/article
Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa
Fecha
2019-04Registro en:
Aguirre Pranzoni, Celeste Beatriz; Tosso, Rodrigo David; Bisogno, Fabricio Román; Kurina Sanz, Marcela Beatriz; Orden, Alejandro Agustin; Preparation of chiral β-hydroxytriazoles in one-pot chemoenzymatic bioprocesses catalyzed by Rhodotorula mucilaginosa; Elsevier; Process Biochemistry; 79; 4-2019; 114-117
1359-5113
CONICET Digital
CONICET
Autor
Aguirre Pranzoni, Celeste Beatriz
Tosso, Rodrigo David
Bisogno, Fabricio Román
Kurina Sanz, Marcela Beatriz
Orden, Alejandro Agustin
Resumen
Chemoenzymatic strategies for the preparation of enantiopure β-hydroxytriazoles were designed. These and other related compounds are particularly relevant because of their antitubercular bioactivities and as β-adrenergic receptor blockers. The ability of Rhodotorula mucilaginosa LSL to stereoselectively reduce prochiral ketones coupled to copper(I)-catalyzed azide-alkyne cycloaddition was exploited. The reactions were performed in aqueous medium and at room temperature. R. mucilaginosa LSL offered the advantage of internal redox cofactor recycling. Notably, the biocatalyst was compatible with all the chemicals required namely sodium azide, copper sulfate and alkynes and showed a broad substrate scope reducing small-bulky and bulky-bulky ketones stereoselectively. Considering this, two one-pot processes were assessed to synthesize enantiopure (R)-β-hydroxytriazoles. A one-pot, three-step sequential transformation allowed obtaining enantiopure products up to 65% yield starting from α-chloro arylketones. On the other hand, with α-bromo arylketones, a one-pot cascade process furnished the same products in ca 80% isolated yield.