Biosynthesis of alkyne moiety in natural products and application of alkyne biosynthetic machineries

LYU Jianming; ZHAO Huan; HU Dan; GAO Hao

doi:10.12211/2096-8280.2021-056

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Biosynthesis of alkyne moiety in natural products and application of alkyne biosynthetic machineries

Invited Review | 更新时间：2026-03-18

- Biosynthesis of alkyne moiety in natural products and application of alkyne biosynthetic machineries
- Synthetic Biology Journal Vol. 2, Issue 5, Pages: 734-750(2021)
- 作者机构：
  
  1.暨南大学药学院，中药及天然药物研究所，广东　广州　510632
  2.暨南大学中医学院，广东　广州　510632
- 作者简介：
- 基金信息：
- DOI：10.12211/2096-8280.2021-056
  CLC： Q81
- Received：07 May 2021，
  
  Revised：2021-07-25，
  
  Published：31 October 2021
- 稿件说明：
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吕建明，赵欢，胡丹，高昊. 天然产物中炔基的生物合成机制研究及其应用［J］. 合成生物学， 2021， 2（5）： 734-750

LYU Jianming， ZHAO Huan， HU Dan， GAO Hao. Biosynthesis of alkyne moiety in natural products and application of alkyne biosynthetic machineries［J］. Synthetic Biology Journal， 2021， 2（5）： 734-750
吕建明，赵欢，胡丹，高昊. 天然产物中炔基的生物合成机制研究及其应用［J］. 合成生物学， 2021， 2（5）： 734-750 DOI： 10.12211/2096-8280.2021-056.

LYU Jianming， ZHAO Huan， HU Dan， GAO Hao. Biosynthesis of alkyne moiety in natural products and application of alkyne biosynthetic machineries［J］. Synthetic Biology Journal， 2021， 2（5）： 734-750 DOI： 10.12211/2096-8280.2021-056.

摘要

炔基是许多药物、活性天然产物以及功能材料等的重要官能团，因此，开发高效的炔类化合物合成策略具有重要意义。传统的合成策略包括通过化学反应直接制备，或以简单的炔类前体为底物，通过生物转化获得。随着合成生物学技术的飞速发展，从头生物合成有望成为炔类化合物合成的新策略。该策略绿色环保，易于操作，是对传统化学合成以及生物转化策略的有效补充。炔类化合物从头生物合成的关键是阐明天然产物中炔基的生物合成机制，获得炔基合成酶。本文重点总结了不同天然产物中炔基的生物合成研究进展，包括脂肪酸、聚酮、聚酮-非核糖体肽杂合体、氨基酸以及杂萜，并介绍了炔基合成酶在炔类化合物从头生物合成中的应用。尽管炔基的生物合成研究近年来取得了长足发展，但在炔基合成酶的种类挖掘及其底物特异性拓展方面还有待进一步加强，从而为炔类化合物的从头生物合成提供更多可供选择的酶工具。

Abstract

Alkyne is a biologically significant moiety in many drugs and natural products

which is also a versatile buildin

g block in modern chemistry. Therefore

it is of great importance to efficiently synthesize alkyne-containing products in the fields of medicinal chemistry

organic chemistry

chemical biology and so on. Generally

alkyne-containing products are obtained

via

chemical synthesis

but this strategy often suffers from high cost

low efficiency and harsh reaction conditions. Alternatively

microbial biotransformation can be performed through feeding alkyne-containing precursors

but it is still challenging since these precursors are not easily accessible. Inspired by the advancement of synthetic biology

de novo

biosynthesis is expected to be a promising approach for producing acetylenic products

which is environmentally friendly and industrially tractable. Great efforts have thus been devoted to elucidating the biosynthetic machinery of alkyne moiety in natural products so as to provide efficient enzymatic tools for the

de novo

biosynthesis of acetylenic products. In this review

we comment recent progress in biosynthesis of alkynes in different natural products. In unsaturated fatty acids

a special family of desaturases serve as acetylenases

converting olefinic bonds to triple bonds

via

-dependent dehydrogenation with the use of a diiron active site. In polyketides

although lots of work has been done in revealing the biosynthetic routes of enediyne antibiotics

the genetic basis for synthesizing acetylenic bonds in their core backbones remains enigmatic. In polyketide-non ribosomal peptide hybrid molecules

the three-gene cassette encoding the ligase

acyl carrier protein (ACP) and acetylenase is responsible for the formation of the terminal alkyne-labeled fatty acyl-ACP

which is then used as the starting unit to be incorporated into the assembly line. In amino acids

the halogenase catalyzes the side-chain halogenation followed by the oxidase-mediated side-chain cleavage

and then the lyase catalyzes the elimination reaction to co

nvert resulted alkene to the terminal triple bond. In meroterpenoids

the cytochrome P450 oxidase can consecutively catalyze two rounds of dehydrogenation to provide the internal alkyne in the prenyl chain. Moreover

we also introduce

de novo

biosynthesis of the terminal-alkyne tagged polyketides and proteins on the basis of the characterized biosynthetic machineries of alkynes. Despite the great progress in alkyne biosynthesis

it needs to be further strengthened in exploring the types of alkyne synthases as well as expanding their substrate specificity

so as to provide more enzymatic tools for the

de novo

biosynthesis of alkyne-containing products.

关键词

Keywords

references

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