Enzyme-catalyzed Hetero-Diels-Alder reactions

WANG Cuizhen; CHEN Tiao; WANG Jianbo

doi:10.12211/2096-8280.2023-015

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Enzyme-catalyzed Hetero-Diels-Alder reactions

Invited Review | 更新时间：2025-03-20

- Enzyme-catalyzed Hetero-Diels-Alder reactions
- Synthetic Biology Journal Vol. 5, Issue 1, Pages: 107-125(2024)
- 作者机构：
  
  1.湖南师范大学化学化工学院，化学生物学及中药分析教育部重点实验室，植化单体开发与利用湖南省重点实验室，湖南长沙 410081
  2.浙江大学基础医学院药物生物技术研究所，浙江大学医学院附属第二医院综合ICU科室，浙江杭州 310030
- 作者简介：
- 基金信息：
- DOI：10.12211/2096-8280.2023-015
  CLC： Q55
- Received：21 February 2023，
  
  Revised：2023-05-29，
  
  Published：29 February 2024
- 稿件说明：
移动端阅览
王翠珍，陈窕，王健博. 酶催化杂Diels-Alder反应［J］. 合成生物学， 2024， 5（1）： 107-125

WANG Cuizhen， CHEN Tiao， WANG Jianbo. Enzyme-catalyzed Hetero-Diels-Alder reactions［J］. Synthetic Biology Journal， 2024， 5（1）： 107-125
王翠珍，陈窕，王健博. 酶催化杂Diels-Alder反应［J］. 合成生物学， 2024， 5（1）： 107-125 DOI： 10.12211/2096-8280.2023-015.

WANG Cuizhen， CHEN Tiao， WANG Jianbo. Enzyme-catalyzed Hetero-Diels-Alder reactions［J］. Synthetic Biology Journal， 2024， 5（1）： 107-125 DOI： 10.12211/2096-8280.2023-015.

摘要

Diels-Alder反应被认为是合成复杂天然产物的最有效的方法之一，一直以来都深受化学家的关注。而杂原子参与的HDA（Hetero-Diels-Alder）反应是合成各种天然杂环的重要工具，其中以氧杂DA反应和氮杂DA反应最为常见。酶催化HDA反应以其绿色温和、高效、高选择性等优势受到人们广泛关注。随着杂环天然产物中酶催化HDA反应的不断发现，对HDA相关酶的立体选择性、底物特异性的研究也不断深入，有效促进了人们对这一类酶序列与功能关系的了解，为其挖掘和改造奠定了基础。本文集中对目前已知的酶催化HDA反应合成杂环天然产物的成果进行概述，主要包括吡喃类化合物和吲哚生物碱生物合成中涉及的酶促HDA反应，以期通过对途径和催化机理的分析，为发展新的相关生物催化剂用于合成非天然的杂环产物提供思路。

Abstract

The Diels-Alder reaction is a chemical process where a conjugated diene reacts with a dienophile to form cyclohexene. This reaction can generate up to four adjacent chiral centers and two carbon-carbon bonds simultaneously

making it an effective method to form C—C bonds. Therefore

it has attracted wide attention. Hetero-Diels-Alder (HDA) reactions

which involve heteroatoms

are an important tool for synthesizing natural heterocyclic rings. HAD reaction types are classified according to the heteroatoms involved

with the most common types being oxa Diels-Alder reaction and aza Diels-Alder reaction. At present

non-enzyme catalysts have been successfully applied to catalyze HDA reactions

which are catalyzed by chemical catalysts such as Lewis acids

metal ions

and organic molecules can do. However

compared to chemical catalysis

enzyme-catalyzed HDA reactions are favored due to their green

mild

efficient

and highly selective properties. With the discovery of enzyme-catalyzed HDA reactions in natural product biosynthetic pathways

uncovering the stereoselectivity and substrate specificity of HDA-related enzymes promotes our understandings of the relationship between sequences and functions. Additionally

it lays the foundation for further mining and modification of enzymes. However

there are several challenges need to be tackled. Firstly

although a few HDA enzymes have been studied

the vast majority are remained to be isolated and characterized. Secondly

the catalytic mechanisms of most reported HDA enzymes are not clear

and more information about their structures

key residues and catalytic processes remains to be uncovered. Thirdly

all reported cases present rather narrow substrate spectra

and the stereoselectivity is rather poor. Here

we summarize the currently known enzyme-catalyzed HDA reactions in heterocyclic natural product biosynthetic pathways

focusing mainly on those involved in the biosynthesis of pyridines and indole alkaloids. By summarizing and analyzing the entire biocatalytic pathways and catalytic mechanisms

we expect to guide further research and engineering of HAD enzymes to improve their activity and selectivity. We also hope to inspire the development of new biocatalysts for the synthesis of non-natural heterocyclic products.

关键词

Keywords

references

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Scalable mining of proteins for biocatalysis via synthetic biology

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Key Laboratory of Chemical Biology and Analysis of Traditional Chinese Medicine， Ministry of Education and Key Laboratory of Phytochemical Monomer Development and Utilization， Hunan Normal University

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