Modular Chemoenzymatic Cascade for Highly Diastereo- and Enantioselective Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-03-18 DOI:10.1021/acscatal.5c01322

Honghui Zhang, Yan Zhang, Changtong Zhu, Zhiwei Deng, Luyun Ji, Dejing Yin, Changmei Liu, Zhengshan Luo, Zhenbo Yuan, Yijian Rao

引用次数: 0

Abstract

1,3-Disubstituted tetrahydroisoquinolines (THIQs) are widespread structural skeletons among alkaloid natural products with diverse biological activities. The lack of their unambiguous biosynthetic pathways to produce these structures has, however, impeded their efficient production through environmentally friendly biosynthesis. Herein, a modular chemoenzymatic cascade has been developed to circumvent this limitation for the synthesis of various 1,3-disubstituted THIQs bearing two stereo carbon centers with high diastereo- and enantioselectivities after the semirational design of the imine reductase SnIR. More importantly, the preparative stereodivergent synthesis of both cis- and trans-1,3-disubstituted THIQs is achieved through the plug-and-play strategy. Therefore, this work highlights the promising potential of modular chemoenzymatic strategies for the preparation of a series of value-added products and derivatives through synthetic biology.

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.