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

• Main Authors: Iñigo, S., Porro, M.T., Montserrat, J.M., Iglesias, L.E., Iribarren, A.M.
• Format: Journal/Newspaper
• Language: unknown
• Subjects: Deacetylation; Enzymatic alcoholysis; Lipases; Regioselectivity; Ribosides; Acetylation; Alcohols; Catalysis; Enzymes; Stereochemistry; Anomers; Isomers; furan derivative; lipase B; methyl 2,3 di o acetyl alpha dextro ribofuranoside; methyl 2,3,5 tri o acetyl beta dextro ribofuranoside; methyl 2.3.5 tri o acetyl alpha dextro ribofuranoside; methyl dextro riboside; unclassified drug; alcoholysis; article; biocatalyst; Candida antarctica; deprotection reaction; diastereoisomer; enzyme mechanism; temperature sensitivity; Antarc*; Antarctica
• Online Access: https://hdl.handle.net/20.500.12110/paper_13811177_v35_n1-3_p70_Inigo

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). © 2005 Elsevier B.V. All rights reserved.