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Synlett 2021; 32(08): 775-784
DOI: 10.1055/s-0040-1707320
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Exploration of Iron- and α-Ketoglutarate-Dependent Dioxygenases as Practical Biocatalysts in Natural Product Synthesis

Hans Renata  ∗
Department of Chemistry, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL, 33458, USA   Email: hrenata@scripps.edu
› Author AffiliationsThe work described in this Account is supported, in part, by the National Institutes of Health Grant GM128895.
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Abstract

Catalytic C–H oxidation is a powerful transformation with enormous promise to streamline access to complex molecules. In recent years, biocatalytic C–H oxidation strategies have received tremendous attention due to their potential to address unmet regio- and stereoselectivity challenges that are often encountered with the use of small-molecule-based catalysts. This Account provides an overview of recent contributions from our laboratory in this area, specifically in the use of iron- and α-ketoglutarate-dependent dioxygenases in chemoenzymatic syntheses of complex natural products.

1 Introduction

2 Overview of Natural Oxygenases

3 C5 Hydroxylation of Aliphatic Amino Acids

4 Chemoenzymatic Synthesis of Tambromycin

5 Chemoenzymatic Synthesis of Cepafungin I and Related Analogues

6 Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues

7 Conclusion and Future Direction

Key words

C–H hydroxylation - natural products - biocatalysis - total synthesis - amino acids - oxygenases


Publication History

Received: 11 August 2020

Accepted after revision: 06 September 2020

Article published online:
26 October 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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