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Chemoenzymatic Synthesis of 2-Aryl-thiazolines fr

Gao, Feng and Gallou, Fabrice (2024) Chemoenzymatic Synthesis of 2-Aryl-thiazolines fr. Angewandte Chemie. International edition. e202405833.


Nitrogen heterocycles are commonly found in bioactive
natural products and drugs. However, the biocatalytic tools for
nitrogen heterocycle synthesis are very limited. Herein, we report our
discovery of vanillyl alcohol oxidases (VAOs) as an efficient
biocatalyst for the one-pot synthesis of 2-aryl-thiazolines from 4-
hydroxybenzaldehydes and aminothiols. The wild-type biocatalyst is
featured with broad scope of 4-hydroxybenzaldehydes. Though the
scope of aminothiols is limited, it can be overcome via semi-rational
protein engineering, generating a variant that can be used to produce
previously inaccessible cysteine-derived bioactive 2-aryl-thiazolines
using the wild-type VAO. Benefiting from the derivatizable functional
groups in the enzymatic products, these products can be chemically
modified to further expand the chemical space that can be covered by
VAO, offering a new chemoenzymatic strategy for green and
convenient synthesis of structurally diverse 2-aryl-thiazoline
derivatives in drug development.

Item Type: Article
Date Deposited: 02 Jul 2024 00:46
Last Modified: 02 Jul 2024 00:46