Ziyuan WANG1, Lirong YANG1,2, Jianping WU1,2, Wenlong ZHENG1
Received:
2024-02-04
Revised:
2024-05-16
Published:
2024-06-17
Contact:
Wenlong ZHENG
王子渊1, 杨立荣1,2, 吴坚平1,2, 郑文隆1
通讯作者:
郑文隆
作者简介:
基金资助:
CLC Number:
Ziyuan WANG, Lirong YANG, Jianping WU, Wenlong ZHENG. A review on enzyme-catalyzed synthesis of chiral amino acids.[J]. Synthetic Biology Journal, DOI: 10.12211/2096-8280.2024-015.
王子渊, 杨立荣, 吴坚平, 郑文隆. 酶促合成手性氨基酸的研究进展[J]. 合成生物学, DOI: 10.12211/2096-8280.2024-015.
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方法 Methods | 酶制剂 Enzyme | 底物 Substrate | 立体选择性 Stereosele-ctivity | 理论产率 Theoretical yield | 原子经济性 Atomic economy | 典型案例 Typical examples |
---|---|---|---|---|---|---|
Asymmetric synthesis | Amino acid dehydrogenase, Transaminase, Ammonia lyase, Amino mutase, Aldolase, Hydroxymethyltransferase, etc. | Keto acids, α, β-unsaturated carboxylic acids, Amino acids and Aldehydes | High | 100% | High | L-tert-Leucine [ (R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid [ |
Racemization synthesis | Amino acid dehydrogenase, Transaminase, Ammonia lyase, Amino mutases, Aldolase, Hydroxymethyltransferase, Amino acid oxidase, Amino acid deaminase, Amino acid racemase, etc. | Racemic amino acids | High | 100% | High | L-Phosphinothricin[ L-Phenylglycine [ |
Dynamic kinetic resolution | Amino acid oxidase, Amino acid deaminase, Amino acid dehydrogenase, Amino acid racemase, etc. | Racemic amino acids | High | 50% | Low | — |
Table 1 Comparison of three common methods for enzyme-catalyzed synthesis of chiral amino acids
方法 Methods | 酶制剂 Enzyme | 底物 Substrate | 立体选择性 Stereosele-ctivity | 理论产率 Theoretical yield | 原子经济性 Atomic economy | 典型案例 Typical examples |
---|---|---|---|---|---|---|
Asymmetric synthesis | Amino acid dehydrogenase, Transaminase, Ammonia lyase, Amino mutase, Aldolase, Hydroxymethyltransferase, etc. | Keto acids, α, β-unsaturated carboxylic acids, Amino acids and Aldehydes | High | 100% | High | L-tert-Leucine [ (R)-3-Amino-4-(2,4,5-trifluorophenyl)butyric acid [ |
Racemization synthesis | Amino acid dehydrogenase, Transaminase, Ammonia lyase, Amino mutases, Aldolase, Hydroxymethyltransferase, Amino acid oxidase, Amino acid deaminase, Amino acid racemase, etc. | Racemic amino acids | High | 100% | High | L-Phosphinothricin[ L-Phenylglycine [ |
Dynamic kinetic resolution | Amino acid oxidase, Amino acid deaminase, Amino acid dehydrogenase, Amino acid racemase, etc. | Racemic amino acids | High | 50% | Low | — |
Fig. 3 The structure of glutamate dehydrogenase (A) The crystal structure of glutamate dehydrogenase from Bacillus subtilis (PDB ID: 3K92); (B) The single subunit structure of glutamate dehydrogenase from Bacillus subtilis; (C) The "open" and "close" structure of glutamate dehydrogenase
Fig. 8 The crystal structure of transaminase (A) The crystal structure of (S)-transaminase from Bacillus megaterium (PDB ID: 5G09); (B) The crystal structure of (R)-transaminase from Aspergillus fumigatus (PDB ID: 4UUG)
Fig. 10 Synthesis of chiral α-amino acids by asymmetric transfer of amino groups to keto acids (A) Cascade synthesis of chiral α-amino acids by branched-chain amino acid aminotransferase (BCAT) and ornithine aminotransferase (OrnAT); (B) Cascade synthesis of L-phosphinothricin (L-PPT) by transaminase (TA), glutamate dehydrogenase (GluDH), and alcohol dehydrogenase (ADH); (C) Based on the alanine dehydrogenase (ALD) - formate dehydrogenase (FDH) amine cycle system, cascade synthesis of L-2-aminobutyrate by threonine deaminase (TD) and TA; (D) Chemical methods are coupled with aspartate transaminase (AspAT) to synthesize L-3,4-dimethoxyphenylalanine.
Fig. 12 Synthesis of chiral non-α-amino acids by asymmetric transfer of amino groups to keto acids (A) Coupling different transaminases (TA) to synthesize (S)-4-aminopentanoic acid; (B) Cascade synthesis of (S)-β-phenylalanine by nitrilase and ω-TA
Fig. 14 General catalytic reaction formula for ammonia lyases used for chiral amino acid synthesis (DAL-Aspartate ammonia-lyase, MAL-Methylaspartate ammonia-lyase, PAL-Phenylalanine ammonia-lyase, HAL-Histidine ammonia-lyase, TAL-Tyrosine ammonia-lyase.)
Fig. 16 Enantioselective addition of ammonia to α,β-unsaturated acids by phenylalanine ammonia lyase (PAL) (A) Various aromatic L-amino acids; (B) EMA401 intermediate.
Fig. 18 Enantioselective addition of ammonia to α,β-unsaturated acids by Methylaspartate ammonia lyases (MAL) (A) Vitamin B5 derivatives (B) L-dopa (ADC-aspartate-α-decarboxylase, CrpG-β-methylaspartate-α-decarboxylase, GAD-glutamate decarboxylase, PS-pantothenate synthetase)
Fig. 21 The crystal structure of threonine aldolase (A) The crystal structure of L-threonine aldolase from Aeromonas jandaei (PDB ID: 3WGB); (B) The crystal structure of D-threonine aldolase from Achromobacter xylosoxidans (PDB ID: 4V15)
Fig. 22 The catalytic mechanism of threonine aldolase (A) The catalytic mechanism of L-threonine aldolase; (B) The catalytic mechanism of D-threonine aldolase
Fig. 23 Schematic diagram of the path hypothesis. Aldehydes (MTB) attack Cα of aldimine PLP-Gly through the syn path or anti path to form the corresponding configuration of products[92].
Fig. 27 Amino acid oxidase are involved in in the deracemization synthesis of chiral amino acids (A) L-phosphinothricin; (B) L-2-aminobutyric acid. (AAO-amino acid oxidase, AADH-amino acid dehydrogenase, CAT-catalase, TA-transaminase)
Fig. 30 Amino acid dehydrogenase are involved in in the deracemization synthesis of chiral amino acids (A) D-alanine; (B) L-phenylglycine. (ALADH-alanine dehydrogenase, TA-transaminase, MR-mandelate racemase, DMDH- D-mandelate dehydrogenase, LeuDH-leucine dehydrogenase.)
Fig. 31 Chemo-enzymatic deracemization synthesis of chiral amino acids (A) D-Amino acids; (B) D-Phenylalanine (AAO-amino acid oxidase, PAL-phenylalanine ammonia-lyase, AAD-amino acid deaminase.)
产品 Products | 应用 Applications | 合成路线 Synthetic routes | 酶制剂 Enzyme | 参考文献 References |
---|---|---|---|---|
L-phosphinothricin | Broad-spectrum herbicides | Asymmetric reductive amination of keto acids | Glutamate dehydrogenase, Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ |
Deracemization synthesis | D-amino acid oxidase, catalase, glutamate dehydrogenase, Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ | ||
L-tert-leucine | Intermediate of azanavir, animal feed additive, nutritional fortifier | Asymmetric reductive amination of keto acids | Leucine dehydrogenase,Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ |
Asymmetric transfer of amino groups to keto acids | Transaminase | [ | ||
L-2-aminobutyric acid | Intermediate of antituberculosis ethambutol and antiepileptic drug levetiracetam | Asymmetric reductive amination of keto acids | Leucine dehydrogenase,threonine deaminase,Glucose dehydrogenase | [ |
Asymmetric transfer of amino groups to keto acids | Transaminase,Glutamate dehydrogenase,Alcohol dehydrogenase | [ | ||
Deracemization synthesis | D-amino acid oxidase, ω- Transaminase | [ | ||
L- phenylglycine | Intermediate of β-lactam antibiotics | Asymmetric reductive amination of keto acids | Amino acid dehydrogenase,Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ |
Deracemization synthesis | Mandelate racemase, D-mandelate dehydrogenase, Leucine dehydrogenase | [ | ||
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid | Intermediate of siagliptin | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
L-norvaline | Intermediate of perindopril | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
(2R, 4S) -ethyl-5-([1,1′- biphenyl]-4-yl) -4- ((tert butoxycarbonyl) amino)-2-methylvaleric acid | Intermediate of sacubitril | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
L-3,4-dimethoxyphenylalanine | Drug intermediates, chemical sensors, chiral catalysts, etc | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
(3S)-5-(Benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid | Intermediate of olodanrigan (EMA401) | Enantioselective addition of ammonia to α,β-unsaturated acids | Phenylalanine ammonia-lyase | [ |
(R)-pantothenic acid | Intermediate of antimicrobials against plasmodium falciparum and multidrug-resistant staphylococcus aureus | Enantioselective addition of ammonia to α,β-unsaturated acids | 3-methylaspartate ammonia lyase, Aspartate-α-decarboxylase, β-methylaspartate-α-decarboxylase/glutamate decarboxylase, Pantothenate synthetase | [ |
L-syn-p-methylsulfonylphenylserine | Intermediate of flufenicol | Aldol condensation of an amino acid to aldehydes | L-threonine aldolase | [ |
β-(2-furyl)serine | Intermediate of furan antibiotic and 2-amino-1-(2-furanyl)ethanol | Aldol condensation of an amino acid to aldehydes | L-threonine aldolase | [ |
Table 2 Partially applied enzymatic synthetic routes in production
产品 Products | 应用 Applications | 合成路线 Synthetic routes | 酶制剂 Enzyme | 参考文献 References |
---|---|---|---|---|
L-phosphinothricin | Broad-spectrum herbicides | Asymmetric reductive amination of keto acids | Glutamate dehydrogenase, Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ |
Deracemization synthesis | D-amino acid oxidase, catalase, glutamate dehydrogenase, Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ | ||
L-tert-leucine | Intermediate of azanavir, animal feed additive, nutritional fortifier | Asymmetric reductive amination of keto acids | Leucine dehydrogenase,Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ |
Asymmetric transfer of amino groups to keto acids | Transaminase | [ | ||
L-2-aminobutyric acid | Intermediate of antituberculosis ethambutol and antiepileptic drug levetiracetam | Asymmetric reductive amination of keto acids | Leucine dehydrogenase,threonine deaminase,Glucose dehydrogenase | [ |
Asymmetric transfer of amino groups to keto acids | Transaminase,Glutamate dehydrogenase,Alcohol dehydrogenase | [ | ||
Deracemization synthesis | D-amino acid oxidase, ω- Transaminase | [ | ||
L- phenylglycine | Intermediate of β-lactam antibiotics | Asymmetric reductive amination of keto acids | Amino acid dehydrogenase,Alcohol dehydrogenase/Glucose dehydrogenase/Formate dehydrogenase | [ |
Deracemization synthesis | Mandelate racemase, D-mandelate dehydrogenase, Leucine dehydrogenase | [ | ||
(R)-3-amino-4-(2,4,5-trifluorophenyl)butyric acid | Intermediate of siagliptin | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
L-norvaline | Intermediate of perindopril | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
(2R, 4S) -ethyl-5-([1,1′- biphenyl]-4-yl) -4- ((tert butoxycarbonyl) amino)-2-methylvaleric acid | Intermediate of sacubitril | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
L-3,4-dimethoxyphenylalanine | Drug intermediates, chemical sensors, chiral catalysts, etc | Asymmetric transfer of amino groups to keto acids | Transaminase | [ |
(3S)-5-(Benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid | Intermediate of olodanrigan (EMA401) | Enantioselective addition of ammonia to α,β-unsaturated acids | Phenylalanine ammonia-lyase | [ |
(R)-pantothenic acid | Intermediate of antimicrobials against plasmodium falciparum and multidrug-resistant staphylococcus aureus | Enantioselective addition of ammonia to α,β-unsaturated acids | 3-methylaspartate ammonia lyase, Aspartate-α-decarboxylase, β-methylaspartate-α-decarboxylase/glutamate decarboxylase, Pantothenate synthetase | [ |
L-syn-p-methylsulfonylphenylserine | Intermediate of flufenicol | Aldol condensation of an amino acid to aldehydes | L-threonine aldolase | [ |
β-(2-furyl)serine | Intermediate of furan antibiotic and 2-amino-1-(2-furanyl)ethanol | Aldol condensation of an amino acid to aldehydes | L-threonine aldolase | [ |
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