Biocatalysis C—C bonding reaction and its application

doi:10.11949/0438-1157.20201098

Abstract

Abstract:

The C—C bond formation reaction is the key reaction to construct the carbon skeleton of organic molecules in organic synthesis. This review presents the key enzymes that catalyze C—C bond formation reactions such as Aldol, Acyloin condensation, Stetter, Pictet-Spengler, etc., and the application progress of those enzymes in the synthesis fine chemicals such as β-hydroxy-α-amino, α-hydroxyketone, 1,4-diketone, β-carboline and tetrahydroisoquinoline in recent years. In addition, this manuscript also describes the application prospects of biocatalysis C—C bond formation reactions to expand the application scope of biocatalysis in chemical production.

Key words: C—C bond, biocatalysis, enzyme, catalyst, fine chemicals, application prospects

摘要：

C—C成键反应是有机合成中构建有机分子碳骨架的关键反应。综述了近年来生物催化Aldol、Acyloin condensation、Stetter 、Pictet-Spengler 等C—C成键反应的关键酶制剂，以及这些酶制剂催化合成β-羟基-α-氨基、α-羟基酮、1，4-二酮、β-咔啉、四氢异喹啉等精细化学品的研究进展。此外，还对生物催化C—C成键反应的应用前景进行了展望，从而扩大生物催化在化学品生产中的应用范围。

关键词: C—C成键, 生物催化, 酶, 催化剂, 精细化学品, 应用前景

CLC Number:

Q 814.9

QI Na, SONG Wei, LIU Liming, WU Jing. Biocatalysis C—C bonding reaction and its application[J]. CIESC Journal, 2021, 72(1): 216-228.

齐娜, 宋伟, 刘立明, 吴静. 生物催化C—C成键反应及其应用[J]. 化工学报, 2021, 72(1): 216-228.

Figures/Tables 10

Table 1 Biocatalytic C—C bond formation reaction and fine chemicals generated at the C—C bond site

Reaction	Enzyme	Product	Ref.
oxidative C—C coupling	^Mtlaccase	benzo furan	[3]
oxidative C—C coupling	^EnBBE	berbenrine	[4]
cyclization reaction	^BmSHC	hopene	[5-6]
Suzuki-Miyaura	Suzukiase	Atropisomerci biaryls	[7]
Aldol	^RmFruA/ ^EcFucA/^EcTagA/ ^EcRhaD	polyhydroxy compounds	[8]
Aldol	^AvDTA/^AvLTA/^StSHMT_Sth	β-hydroxy-α-amino	[8]
Acyloin condensation	^ACDH/^PfBAL	PAC/2-HPP	[9]
Acyloin condensation	^PpYerE/^BsAAS	tert-α-hydroxy ketone	[9]
Stetter	^SmPigD/^HcHapD	1,4-dicarbonyls	[10]
Pictet-Spengler	^Rs/OpSTR	β-carbolines	[11]
Pictet-Spengler	^Tf/CjNCS	Tetrahydroisoquinolines	[11]

Table 2 Green synthesis of rare sugars and their derivatives by DHAP aldolase

Aldolase	Yield	Diastereo ratio
FruA	35.7%	92∶8
FruA	23.4%	92∶8
FruA	2.8%	92∶8
FruA	4.7%	87∶13
FucA	35.6%	92∶8
RhaD	10.4%	49∶51
RhaD	10.6%	49∶51
RhaD	22.4%	89∶11

Fig.1 FSA catalyzes C—C bonds to form polyhydroxy compounds

Fig.2 Synthesis of β - hydroxy - α - amino compounds catalyzed by threonine aldolase

Fig.3 ThDP-dependent enzymes catalyze the ketol condensation reaction to form secondary-α-hydroxyketone

Fig.4 YerE catalyzes the formation of C—C bonds for the preparation of tertiary-α-hydroxy ketones

Fig.5 AO: DCPIP uses 2,3-butanedione as an acetyl anion donor to catalyze the formation of tertiary alcohols

Fig.6 ThDP-dependent enzymes catalyze α, β-unsaturated ketones to produce 1,4-dicarbonyl compounds

Fig.7 Pictet-Spengler reaction catalyzed by strictosidine synthase

Fig.8 NCS-Tf mutant catalyzed synthesis of 1,1'-disubstituted THIQ

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