In:
Angewandte Chemie, Wiley, Vol. 135, No. 33 ( 2023-08-14)
Abstract:
C( sp 3 )−H oxyfunctionalization, the insertion of an O‐atom into C( sp 3 )−H bonds, streamlines the synthesis of complex molecules from easily accessible precursors and represents one of the most challenging tasks in organic chemistry with regard to site and stereoselectivity. Biocatalytic C( sp 3 )−H oxyfunctionalization has the potential to overcome limitations inherent to small‐molecule‐mediated approaches by delivering catalyst‐controlled selectivity. Through enzyme repurposing and activity profiling of natural variants, we have developed a subfamily of α ‐ketoglutarate‐dependent iron dioxygenases that catalyze the site‐ and stereodivergent oxyfunctionalization of secondary and tertiary C( sp 3 )−H bonds, providing concise synthetic routes towards four types of 92 α ‐ and β ‐hydroxy acids with high efficiency and selectivity. This method provides a biocatalytic approach for the production of valuable but synthetically challenging chiral hydroxy acid building blocks.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.33
DOI:
10.1002/ange.202305250
Language:
English
Publisher:
Wiley
Publication Date:
2023
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