Work

Unspecific Peroxygenases for the Enzymatic Removal of Alkyl Protecting Groups in Organic Synthesis

Year: 2025

Type: article

Abstract: -dealkylation reactions. UPO23 exhibited a broad substrate scope and efficiently removed methyl, ethyl, propyl, or allyl groups from protected primary, secondary, tertiary, and benzylic alcohols under ambient conditions. Mechanistic investigations revealed dual reaction pathways for UPO23, hydroxylating either the α-carbon of the alkyl chain of the PG or the substrate scaffold, explaining the formation of deprotected target alcohols as well as further oxidized products. Optimized reaction conditions reduced reaction times from 4 h to 15 min for methyl protected key substrates. Preparative scale reactions with protected benzyl ethers yielded up to 92% of the isolated alcohol products. These findings highlight the versatility of UPO23 and offer scalable, environmentally benign, and enzyme-based deprotection strategies for multistep organic synthesis.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c06385