Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers

• Published in: Journal of Molecular Catalysis B: Enzymatic
• Main Authors: Iñigo, Sabrina, Taverna Porro, Marisa Lia, Montserrat, Javier Marcelo, Iglesias, Luis Emilio, Iribarren, Adolfo Marcelo
• Format: Article in Journal/Newspaper
• Language: English
• Published: Elsevier Science
• Subjects: Deacetylation; Enzymatic Alcoholysis; Lipases; Regioselectivity; Ribosides; https://purl.org/becyt/ford/1.6; https://purl.org/becyt/ford/1; Argentina; Sarmiento; Porro; Quilmes; Antarc*; Antarctica
• Online Access: http://hdl.handle.net/11336/80102

The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-α-d-ribofuranoside in 81% yield in 3 h at 45°C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β-d-ribofuranoside was quantitatively formed at long reaction times (5 days). Fil: Iñigo, Sabrina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina Fil: Taverna Porro, Marisa Lia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina Fil: Montserrat, Javier Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de General Sarmiento. Instituto de Ciencias; Argentina Fil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina Fil: Iribarren, Adolfo Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de Quilmes; Argentina