Progress of biocatalytic deuteration of inert carbon-hydrogen bonds

LOU Yujiao; XU Jian; WU Qi

doi:10.12211/2096-8280.2021-067

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Progress of biocatalytic deuteration of inert carbon-hydrogen bonds

Invited Review | 更新时间：2025-03-20

- Progress of biocatalytic deuteration of inert carbon-hydrogen bonds
- Synthetic Biology Journal Vol. 3, Issue 3, Pages: 530-544(2022)
- 作者机构：
  
  1.浙江大学化学系，浙江杭州 310027
  2.浙江工业大学生物工程学院，浙江杭州 310014
- 作者简介：
- 基金信息：
- DOI：10.12211/2096-8280.2021-067
  CLC： Q816
- Received：18 June 2021，
  
  Revised：2021-11-10，
  
  Published：30 June 2022
- 稿件说明：
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楼玉姣，徐鉴，吴起. 生物催化惰性碳氢键的氘代反应研究进展［J］. 合成生物学， 2022， 3（3）： 530-544

LOU Yujiao， XU Jian， WU Qi. Progress of biocatalytic deuteration of inert carbon-hydrogen bonds［J］. Synthetic Biology Journal， 2022， 3（3）： 530-544
楼玉姣，徐鉴，吴起. 生物催化惰性碳氢键的氘代反应研究进展［J］. 合成生物学， 2022， 3（3）： 530-544 DOI： 10.12211/2096-8280.2021-067.

LOU Yujiao， XU Jian， WU Qi. Progress of biocatalytic deuteration of inert carbon-hydrogen bonds［J］. Synthetic Biology Journal， 2022， 3（3）： 530-544 DOI： 10.12211/2096-8280.2021-067.

摘要

氘代化合物在代谢组学、蛋白质组学以及合成化学中的机理研究等方面都有重要的应用。由于C—D键比C—H键更稳定，可以显著提高氘代药物的体内代谢稳定性和生物半衰期，而随着2017年第1个氘代药物丁苯那嗪上市，氘代化合物的重要性进一步被人们关注，国内外许多研究机构都开启了氘代药的研究。氘代化合物的合成方法通常有化学法和生物法两种，由于生物酶与传统的化学催化剂相比具有绿色、低毒、节约成本等优势，并且具有突出的立体选择性，生物催化方法受到了越来越多的关注。本文重点综述了目前已报道的合成氘代化合物的生物催化方法，主要包括生物催化氢氘交换、还原氘代、脱羧氘代等3类反应，这些反应的基本模式都是从氘代水溶剂中汲取氘代质子转移到惰性碳氢键的特定氢原子上。虽然生物酶法制备氘代化合物的研究才刚刚起步，鉴于氘代分子在医药、化学中的重要地位，生物催化氘代反应在未来将会得到越来越广泛的应用。

Abstract

Deuterated compounds display unique properties

and thus have important applications in chemistry

biology

and related areas. For example

deuterated compounds are widely used in elucidating reaction mechanism in organic synthesis because deuterium atom has similar chemical reactivities to hydrogen atom but different magnetic property and mass. In pharmaceutical industry

deuterium-labeled compounds are used for improving the metabolism and pharmacokinetic properties of newly developed pharmaceuticals due to the higher chemical inertness of C—D bonds compared with the C—H bonds. The first deuterated drug

Austedo

was approved in 2017 by the US Food and Drug Administration

which has greatly stimulated the research of deuterium incorporation in pharmaceuticals.Traditional chemical methods for introducing deuterium into compounds rely heavily on transition metal catalysis performed under harsh reaction conditions using complicated ligands with low selectivity

which limit their broad applications. Thus

developing an effective

highly selective

low-cost

and environmental-friendly process for deuteration is highly desirable. Comparing with chemical catalysts

enzymes offer a powerful route for producing chemicals due to their green nature and high selectivity. Thus

biocatalysis has been regarded as an attractive strategy for deuteration. So far

to the best of our knowledge

reported biocatalytic deuteration methods mainly include three types: hydrogen deuterium exchange (HDE)

reduction deuteration and decarboxylation deuteration. The biocatalytic production of HDE is the most efficient synthesis process with good atom-economy

which mostly effectively introduces the isotope into the

-position of the carboxyl group. Bioreductive deuteration usually uses a NADH-dependent reductase with D

O to construct deuterated chiral alcohols or amines. The decarboxylation deuteration offers good selectivity to introduce deuterium into the carboxyl group using carboxylic acids as low-cost starting materials. In this review

we describe recent advances in the three types of biocatalytic deuteration processes respectively. In these cases

O is used as the main source for deuterium atoms. Although studies on the preparation of deuterated compounds by biocatalysis are still in the initial stage

it is expected to be flourish rapidly due to the importance of deuterated compounds.

关键词

Keywords

references

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