生物催化C—C成键反应及其应用

doi:10.11949/0438-1157.20201098

摘要/Abstract

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

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

中图分类号:

Q 814.9

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.

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

图/表 10

表1 生物催化C—C成键反应及其在合成精细化学品中的应用

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]

表2 依赖DHAP醛缩酶绿色合成稀有糖及其衍生物

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

图1 FSA催化C—C键形成多羟基化合物

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

图2 苏氨酸醛缩酶催化形成的β-羟基-α-氨基化合物

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

图3 ThDP依赖的酶催化酮醇缩合反应合成仲-α-羟基酮化合物

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

图4 YerE催化C—C键的形成用于制备叔-α-羟基酮

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

图5 AO:DCPIP使用2,3-丁二酮作为乙酰阴离子供体催化生成叔醇

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

图6 ThDP依赖的酶催化α, β-不饱和酮生成1,4-二羰基化合物

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

图7 异胡豆苷合酶催化的Pictet-Spengler反应

Fig.7 Pictet-Spengler reaction catalyzed by strictosidine synthase

图8 NCS-Tf突变体催化合成1,1'-双取代的THIQ

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

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