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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
Enzyme-Based Organic Synthesis An insightful exploration of an increasingly popular technique in organic chemistry In Enzyme-Based Organic Synthesis, expert chemist Dr. Cheanyeh Cheng delivers a comprehensive discussion of the principles, methods, and applications of enzymatic and microbial processes for organic synthesis. The book thoroughly explores this growing area of green synthetic organic chemistry, both in the context of academic research and industrial practice. The distinguished author provides a single point of access for enzymatic methods applicable to organic synthesis and focuses on enzyme catalyzed organic synthesis with six different classes of enzyme. This book serves as a link between enzymology and biocatalysis and serves as an invaluable reference for the growing number of organic chemists using biocatalysis. Enzyme-Based Organic Synthesis provides readers with multiple examples of practical applications of the main enzyme classes relevant to the pharmaceutical, medical, food, cosmetics, fragrance, and health care industries. Readers will also find: * A thorough introduction to foundational topics, including the discovery and nature of enzymes, enzyme structure, catalytic function, molecular recognition, enzyme specificity, and enzyme classes * Practical discussions of organic synthesis with oxidoreductases, including oxidation reactions and reduction reactions * Comprehensive explorations of organic synthesis with transferases, including transamination with aminotransferases and phosphorylation with kinases * In-depth examinations of organic synthesis with hydrolases, including the hydrolysis of the ester bond Perfect for organic synthetic chemists, chemical and biochemical engineers, biotechnologists, process chemists, and enzymologists, Enzyme-Based Organic Synthesis is also an indispensable resource for practitioners in the pharmaceutical, food, cosmetics, and fragrance industries that regularly apply this type of synthesis.
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Seitenzahl: 963
Veröffentlichungsjahr: 2022
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Table of Contents
Cover
Title Page
Copyright Page
Preface
Acknowledgements
1 Introduction
1.1 Discovery and Nature of Enzyme
1.2 Enzyme Structure and Catalytic Function
1.3 Cofactors and Coenzymes
1.4 Molecular Recognition and Enzyme Specificity
1.5 Enzyme Classes and Nomenclature
1.6 Enzyme and Green Chemistry
1.8 The Winner of Year 2009: A Solvent‐Free Biocatalytic Process for Cosmetic and Personal Care Ingredients
References
2 Organic Synthesis with Oxidoreductases
2.1 Oxidation Reactions
2.2 Reduction Reactions
References
3 Organic Synthesis with Transferases
3.1 Transamination with Aminotransferases
3.2 Glycosyl‐transfer with glycosyltransferase
3.3 Phosphorylation with Kinases
3.4 Acetyl Group Transfer with Acetyltransferase
References
4 Organic Synthesis with Hydrolases
4.1 Hydrolysis of Ester Bond
4.2 Hydrolysis of Amide Bond
4.3 Hydrolysis of Phosphate Esters
4.4 Hydrolysis of Epoxides
4.5 Hydrolysis of Hydantoins
4.6 Hydrolysis of Glycosidic Bonds and Natural Polysaccharide
References
5 Organic Synthesis with Lyases
5.1 Lyases with Carbon–Carbon Bonds
5.2 Lyases with Carbon–Oxygen Bonds
5.3 Lyases with Carbon–Nitrogen Bonds
5.4 Lyases with Carbon–Sulfur Bonds
5.5 Lyases with Carbon–Halide Bonds
References
6 Organic Synthesis with Isomerases
6.1 Racemases and Epimerases
6.2 Cis‐Trans Isomerase
6.3 Intramolecular Oxidoreductases
6.4 Intramolecular Transferases
6.5 Intramolecular Lyases
References
7 Organic Synthesis with Ligases
7.1 Ligases for Carbon–Oxygen Bonds Formation
7.2 Ligases for Carbon–Sulfur Bonds Formation
7.3 Ligases for Carbon–Nitrogen Bonds Formation
7.4 Ligases for Carbon–Carbon Bonds Formation
References
8 Future Perspectives
8.1 Combinatorial Enzymatic Organic Synthesis
8.2 Artificial Intelligence Assisted Enzymatic Organic Synthesis
References
Index
End User License Agreement
List of Tables
Chapter 1
Table 1.1 Turnover numbers for some enzymes.
Table 1.2 Some inorganic metal ions as cofactor of enzymes.
Table 1.3 Some coenzymes as transient carriers of specific atoms or functio...
Table 1.4 Six major classes of enzyme.
Table 1.5 Twelve principles of green chemistry.
List of Illustrations
Chapter 1
Scheme 1.1 The primary structure of a polypeptide chain linked by the peptid...
Scheme 1.2 The proposed enzyme reaction mechanism by Michaelis and Menten.
Scheme 1.3 A generalized enzyme‐catalyzed reaction.
Figure 1.1 The number of binding sites of a substrate with enzyme determines...
Figure 1.2 Three‐point attachment rule shows that only one enantiomer of the...
Figure 1.3 The stereospecificity of enzyme for two substrate enantiomers by ...
Scheme 1.4 Enantioselective synthesis of (3
aS
,6
aR
)‐lactone.
Scheme 1.5 The enantioselective conversion of HPMAE to (
S
)‐phenylephrine....
Scheme 1.6 Regio‐ and stereoselective concurrent oxidations of racemic vicin...
Chapter 2
Scheme 2.1 Oxidation of benzyl alcohol using an oxidase and a catalase.
Scheme 2.2 Oxidation of benzyl alcohol via alcohol dehydrogenases or microbi...
Scheme 2.3 Regio‐ and stereoselective concurrent oxidations of (±)‐1,2 diols...
Scheme 2.4 Deracemization of racemic 1‐phenyl‐1,2‐ethanediol by
C. parapsilo
...
Scheme 2.5 Biocatalytic racemization of
sec
‐alcohols and acyloins using lyop...
Scheme 2.6 Oxidation of an alcohol intermediate to the precursor of atranori...
Scheme 2.7 Bioconversion of isoeugenol to vanillin and vanillic acid by
N. i
...
Figure 2.1 Hydroxylation of alkanes by cytochrome P450 monooxygenase (CYP)....
Scheme 2.8 Terminal hydroxylation of long‐chain alkanes by LadA.
Scheme 2.9 Hydroxylation of alkanes by fungal peroxygenase.
Scheme 2.10 The catalytic hydroxylation of
L
‐phenylalanine and
L-
tyrosine by...
Scheme 2.11 Hydroxylation of naringenin in the culture of the recombinant
S.
...
Scheme 2.12 Hydroxylation of isoliquiritigenin in human liver by cytochrome ...
Scheme 2.13 Hydroxylation of
d
‐amphetamine by cytochrome P450 to give
p
‐hydr...
Scheme 2.14 Catabolic pathways of monosubstituted benzene to diol via
cis
‐di...
Scheme 2.15 Chemoenzymatic preparation of pancratistatin analogs.
Scheme 2.16 Whole‐cell fermentation of methyl 2‐iodobenzoate for organic syn...
Scheme 2.17 Toluene dioxygenase catalyzed
cis
‐dihydroxylation of phenols tow...
Scheme 2.18 Naphthalene dioxygenase catalyzed
cis
‐dihydroxylation of naphtha...
Scheme 2.19 Regioselective oxidation of biphenyl by the
Rhodococcus
sp. DK17...
Scheme 2.20 Postulated reaction mechanism for the formation of thymol from
p
Scheme 2.21 The epoxidation reaction catalyzed by squalene epoxidase (SE).
Scheme 2.22 The synthesis of enantiopure 2‐amino‐1‐phenyl and 2‐amino‐2‐phen...
Scheme 2.23 Epoxidation of ally phenyl ether for producing chiral phenyl gly...
Scheme 2.24 Stereoselective epoxidation of unsaturated bicyclic γ‐lactones....
Scheme 2.25 Synthesis of optically pure
S
‐sulfoxide by co‐expressed
E. coli
....
Scheme 2.26 The multiple enzyme biosynthesis of ω‐hydroxyundec‐9‐enoic acid ...
Scheme 2.27 The Baeyer–Villiger oxidation of cyclohexanone to ε‐caprolactone...
Scheme 2.28 Enantiopure asymmetric microbial Baeyer–Villiger oxidation of ra...
Scheme 2.29 Enantioselective 2‐hydroperoxylation of saturated and unsaturate...
Scheme 2.30 Peroxidation of linoleic acid with soybean lipoxygenase and subs...
Scheme 2.31 Mn‐LO mediated peroxidation of linoleic acid.
Scheme 2.32 Kinetic resolution of aryl hydroperoxides by HRP.
Scheme 2.33 Enantioselectivities of the selenosubtilisin‐catalyzed kinetic r...
Scheme 2.34 Asymmetric reduction of ketone precursor
o
‐chloroacetophenone wi...
Figure 2.2 Structure of aprepitant.
Scheme 2.35 The asymmetric synthesis of 3,5‐bis(trifluoromethyl) acetophenon...
Scheme 2.36 Bioreduction of α‐haloketones in aqueous medium using different ...
Scheme 2.37
E. coli
or
S. cerevisiae
catalyzed reduction of bicycle[2.2.2]oc...
Scheme 2.38 Yeast mediated enantioselective reduction of ethyl benzoylacetat...
Scheme 2.39 Asymmetric reduction of ketones and polymerization of the optica...
Scheme 2.40 Asymmetric reduction of activated alkene substrates catalyzed by...
Scheme 2.41 Asymmetric reduction of α‐methylmaleic acid dimethylester with
Z
...
Scheme 2.42 Asymmetric bioreduction of citraconic acid dimethylester via a c...
Scheme 2.43 BY fermentations and OYEs 1–3 mediated bioreductions of substrat...
Scheme 2.44 The reduction of γ,δ‐double bond of the conjugated lactone in se...
Chapter 3
Scheme 3.1 The transamination between acetophenone and excessive isopropyl a...
Scheme 3.2 Enzyme cascade reactions for the conversion of
L
‐threonine to
L
‐h...
Scheme 3.3 The formation of
N
‐benzylacetamide from benzaldehyde through an e...
Scheme 3.4 The enzymatic cascade route toward all four diastereomers of 4‐am...
Scheme 3.5 The oxidation/transamination cascade reactions for the biosynthes...
Scheme 3.6 Synthesis of sitagliptin from prositagliptin ketone using immobil...
Scheme 3.7 Galactosyltransferase catalyzed glycosylation with UDP‐2‐d‐Gal as...
Scheme 3.8 Method for avoiding product inhibition in GalT‐catalyzed glycosyl...
Scheme 3.9 β‐1,4‐GalT catalyzed galactosylation of natural glycosides and co...
Scheme 3.10 Two‐step synthesis of glycogen with glycogenin functioning as an...
Scheme 3.11 The transfer of γ‐phosphoryl group from ATP to hydroxyl group co...
Scheme 3.12 Phosphorylation of 4HT to 4PHT by kinase DUF1537 for enzyme cofa...
Scheme 3.13 Sequential phosphorylation of peptide R‐SSD3 with casein kinases...
Scheme 3.14 Synthetic pathway of melatonin from serotonin by two kinds of ac...
Scheme 3.15 Protein acetylation with CRTase and DAMC without involving acety...
Chapter 4
Scheme 4.1 Esterase activity with heterotrophic bacteria isolated from neutr...
Scheme 4.2 FRET‐based PLE catalyzed ester hydrolysis.
Scheme 4.3
cis
‐2‐(2‐Methyl‐acryloyloxy‐methyl)‐cyclopropanecarboxylic acid e...
Scheme 4.4 PLE catalyzed hydrolysis of chrysanthemic acid esters: (a)
cis
/
tr
...
Scheme 4.5 Kinetic resolution of racemic ester for producing chiral TA with ...
Scheme 4.6 Esterase‐catalyzed kinetic resolution of racemic IPG esters.
Scheme 4.7 Enantioselective hydrolysis of dimethyl 2‐methyl‐2‐phenylmalonate...
Scheme 4.8 Esterase‐catalyzed enantioselective hydrolysis of 2‐cyano cyclopr...
Scheme 4.9 Lipases‐catalyzed hydrolysis of triacylglycerols.
Scheme 4.10 Enantioselective hydrolysis of (±)‐1,2‐diacetoxy‐3‐chloropropane...
Scheme 4.11 BCL‐catalyzed kinetic resolution of β‐substituted‐γ‐acetyloxymet...
Scheme 4.12
Candida antarctica
lipase B‐catalyzed asymmetric alcoholysis of ...
Scheme 4.13 CPL‐catalyzed kinetic resolution of BPA alkyl esters (a–e) with ...
Scheme 4.14 Kinetic resolution of water‐insoluble α‐acyloxy esters with immo...
Scheme 4.15 Lipase‐mediated biodiesel oil production using ionic liquids as ...
Scheme 4.16 Protease‐catalyzed desymmetrization to form Valganciclovir hydro...
Scheme 4.17 Tandem enzymatic resolution of racemic α‐aminoalkanedioic acid d...
Scheme 4.18 Protease‐catalyzed degradation of TRH in blood, organs, and brai...
Scheme 4.19 Enantioselective hydrolysis of racemic naproxen amide with
R. er
...
Scheme 4.20 Whole cell catalyzed enantioselective biotransformations of race...
Scheme 4.21 Enzymatic hydrolysis pathways for nitrile to form carboxylic aci...
Scheme 4.22 Phosphatases‐catalyzed hydrolysis of a phosphate ester bond.
Scheme 4.23 Coupled enzymes synthesis of L‐fructose from
rac
‐glyceraldehyde ...
Scheme 4.24 T6PP catalyzed hydrolysis of T6P for trehalose biosynthesis.
Scheme 4.25 Kinetic resolution of racemic nitro‐substituted phenoxypropylene...
Scheme 4.26 The enantioselectivity of epoxide hydrolases from two different ...
Scheme 4.27 Enantioselective hydrolysis of racemic 3‐chlorostyrene oxide to ...
Scheme 4.28 Kinetic resolution of racemic epichlorohydrin for producing (
R
)‐...
Scheme 4.29 Enantioconvergent processes for 2‐, 3‐, or 4‐pyridyloxirane by t...
Scheme 4.30 Kinetic resolution of glycidate ester with immobilized crude ext...
Scheme 4.31 Hydrolysis of DL‐5‐monosubstituted hydantoins for optically pure...
Scheme 4.32 Production of
N
‐carbamoyl‐D‐phe derivatives using D‐hydantoinase...
Scheme 4.33 Enantiospecific hydrolysis of fluorinated
rac
‐5‐arylhydantoins w...
Scheme 4.34 Enantioselective synthesis of L‐homophenylalanine by hydantoinas...
Scheme 4.35 The route of hydantoinase catalyzed hydrolysis of racemic 6‐subs...
Figure 4.1 (a) Linear polymer of amylose molecule with α‐D‐1,4‐glycosidic bo...
Figure 4.2 (a) Molecular structure of cellulose with β‐1,4‐glycosidic linkag...
Scheme 4.36 Integrated enzyme cascade‐chemocatalytic cellulose conversion in...
Scheme 4.37 Acetone‐butanol‐ethanol (ABE) produced from rice straw via ethan...
Figure 4.3 Structure of xylan with different side chains attached.
Chapter 5
Scheme 5.1 Stereochemical complementary sets of DHAP‐dependent aldolases....
Scheme 5.2 FSA‐catalyzed self‐aldol addition using glycoaldehyde as the dono...
Scheme 5.3
N
‐Acetylneuraminic acid (NeuAc) aldolase‐catalyzed aldol reaction...
Scheme 5.4 KDPG mutant aldolase accepting nonphosphorylated and altered subs...
Scheme 5.5 Aldol reactions catalyzed by acetaldehyde‐dependent DERA. In comp...
Scheme 5.6 Sequential aldol reaction catalyzed by DERA with acetaldehyde as ...
Scheme 5.7 Application DERA mutant S238D catalyzed sequential on‐pot reactio...
Scheme 5.8 Stereocomplementary aldol reactions with glycine‐dependent ThrAs....
Scheme 5.9 Synthetic application of glycine‐dependent ThrA.
Scheme 5.10 PDC‐catalyzed synthesis of (
R
)‐PAC and its use for the productio...
Scheme 5.11 Direct asymmetric synthesis of meta‐ and
para
‐substituted (
S
)‐be...
Scheme 5.12 Benzoylformate decarboxylase‐mediated asymmetric acyloin condens...
Scheme 5.13 General reaction scheme for BAL‐catalyzed carboligations.
Scheme 5.14 Diastereoselective condensation of benzaldehyde and racemic (±)‐...
Scheme 5.15 (a) BAL‐catalyzed 2,3‐dioxygenated aryl propanones.
Source:
Base...
Scheme 5.16 Acyloin condensation of phenylacetic acid with PhDC.
Scheme 5.17 HNL‐catalyzed enantioselective cyanohydrin formation.
Scheme 5.18 HNL‐catalyzed enantioselective synthesis of cyanohydrins from al...
Scheme 5.19 HNL‐catalyzed enantioselective synthesis of cyanohydrins from ar...
Scheme 5.20 HNL‐catalyzed cyanohydrin formation from 2‐, 3‐, 4‐monosubstitut...
Scheme 5.21 HNL‐catalyzed production of chiral unsaturated cyanohydrins as i...
Scheme 5.22 Chemoenzymatic synthesis of (
R
)‐pantolactone for vitamin B
5
prod...
Scheme 5.23 (
R
)‐HNL‐catalyzed synthesis of (
R
)‐4‐methylsulfanyl‐mandelonitri...
Scheme 5.24 (a) Electrophilic water addition to isolated C=C bonds following...
Scheme 5.25 Hydration of oleic acid by OAH yielding (
R
)‐hydroxystearic acid....
Scheme 5.26 A two‐step process with the combination of oleate hydratase from...
Scheme 5.27 Multistep enzymatic cascade synthesis of α,ω‐dicarboxylic acid, ...
Scheme 5.28 Linalool dehydratase‐isomerase catalyzed transformation of (
S
)‐l...
Scheme 5.29 Limonene hydratase catalyzed addition of water to (
R
)‐(+)‐limone...
Scheme 5.30 Fumarase‐catalyzed hydration of fumarate to form (
S
)‐malate.
Scheme 5.31 Fumarase‐catalyzed synthesis of l‐
threo
‐chloromaleic acid and it...
Scheme 5.32 Malease‐catalyzed water addition of maleic acid to form (
R
)‐mali...
Scheme 5.33 ECH1‐ and ECH2‐catalyzed water addition to
trans
‐2‐enoyl‐CoA thi...
Scheme 5.34 Aspartate ammonia lyase catalyzed reversible deamination reactio...
Scheme 5.35 Industrial synthesis of artificial sweetener aspartame with the ...
Scheme 5.36 Multienzymatic cascade synthesis of l‐phenylalanine from phenylp...
Scheme 5.37 Multienzymatic cascade reaction for the production of β‐alanine ...
Scheme 5.38 Synthesis of
N
‐substituted aspartic acid derivatives with aspart...
Scheme 5.39 Synthesis of enantiopure (
R
)‐3‐aminobutyric acid with mutant asp...
Scheme 5.40 3‐Methylasparte ammonia lyase catalyzes the reversible deaminati...
Scheme 5.41 Synthesis of aspartic acid derivatives with wild‐type CtMAL.
Scheme 5.42 Engineered MAL variants catalyzed amination with broad nucleophi...
Scheme 5.43 Aromatic amino acid ammonia‐lyases catalyzed reversible deaminat...
Scheme 5.44 RgPAL‐catalyzed amination for the synthesis of substituted pheny...
Scheme 5.45 RgPAL‐catalyzed biphasic amination for l‐phenylalanine methyl es...
Scheme 5.46 PAL‐catalyzed deamination of nonaromatic cyclic phenylalanine an...
Scheme 5.47 Synthesis of l‐propargylglycine by PcPAL immobilized on MNPs in ...
Scheme 5.48 Preparation of d‐AADs by kinetic resolution of racemic AADs.
Scheme 5.49 Kinetic resolution of
rac
‐histidine using HAL for simultaneous s...
Scheme 5.50 Synthesis of substituted d‐phenylalanines from corresponding cin...
Scheme 5.51 Synthesis of (
S
)‐β‐arylalanines by the direct amination of aryla...
Scheme 5.52 Kinetic resolution of racemic β‐phenylalanines using coupled PAM...
Scheme 5.53 Kinetic resolution of racemic β‐phenylalanines using coupled Enc...
Scheme 5.54 Three‐step one‐pot chemoenzymatic synthesis of enantiopure aryal...
Scheme 5.55 Two‐step one‐pot chemoenzymatic synthesis of l‐aryalanines from ...
Scheme 5.56 RgPAL‐mediated chemoenzymatic cascade synthesis of (
S
)‐2‐indolin...
Scheme 5.57 Multienzymatic cascade synthesis for substituted
para
‐vinylpheno...
Scheme 5.58 PAL/TAL‐mediated
in vivo
biosynthesis of various secondary metab...
Scheme 5.59 γ‐Cleavage of l‐cystathionine catalyzed by cystathionine γ‐lyase...
Scheme 5.60 β‐elimination reaction with cystathionine β‐lyase to produce cor...
Scheme 5.61 β‐elimination of
S
‐alkyl‐l‐cysteine sulfoxides with alliin lyase...
Scheme 5.62 l‐Methionine degradation catalyzed by methione γ‐lyase to yield ...
Scheme 5.63 Two aerobic biosynthetic pathways for ergothioneine.
Scheme 5.64 Proposed biosynthetic pathway for ovothiol A.
Scheme 5.65 The dehalogenation of a vicinal halohydrin by halohydrin dehalog...
Scheme 5.66 Synthesis of chiral epoxides by HHDH: (a) DehA‐catalyzed reactio...
Scheme 5.67 DKR process of aromatic chlorohydrins catalyzed by HHDH for prod...
Scheme 5.68 HheA10‐catalyzed kinetic resolution of racemic aromatic halohydr...
Scheme 5.69 HHDH‐catalyzed 1,2‐epoxybutane ring opening for yielding various...
Scheme 5.70 Enantioselective epoxide ring‐opening reactions catalyzed by Hhe...
Scheme 5.71 HHDH‐catalyzed synthesis of atorvastatin side‐chain precursor et...
Scheme 5.72 HHDH‐catalyzed one‐pot tandem enantioselective epoxide ring open...
Scheme 5.73 HHDH‐catalyzed regio‐ and enantioselective azidolysis of spiroep...
Scheme 5.74 HheC‐catalyzed nitrite‐mediated ring opening of
p
‐nitrostyrene o...
Scheme 5.75 HHDH‐catalyzed epoxide ring opening with cyanate for chiral oxaz...
Scheme 5.76 Multienzymatic cascade synthesis of β‐substituted alcohols by th...
Scheme 5.77 One‐pot bienzymatic cascade synthesis of ethyl (
R
)‐hydroxyglutar...
Scheme 5.78 Chemoenzymatic cascade synthesis of (S)‐chromanmethanol toward o...
Chapter 6
Scheme 6.1 Racemases catalyzed racemization of amino acids.
Scheme 6.2 Proline racemase catalyzed interconversion of L‐proline to D‐prol...
Scheme 6.3 Diaminopimelate epimerase catalyzed stereoconversion of (L,L)‐2,6...
Scheme 6.4 Amino acid racemase catalyzed isomerization of L‐ or D‐threonine ...
Scheme 6.5 The production of D‐glutamic acid from L‐glutamic acid by enzymat...
Scheme 6.6 Lactate racemase (LarA) catalyzed racemization of D‐ and L‐lactic...
Scheme 6.7 Mandelate racemase catalyzed reversible interconversion of the (
R
Scheme 6.8 Deracemization of
rac
‐mandelate using a stepwise lipase‐mandelate...
Scheme 6.9 One‐pot enzymatic cascade production of methyl (
R
)‐
o
‐chloromande...
Scheme 6.10 One‐pot three‐step enzymatic cascade biotransformation for enant...
Scheme 6.11 Enantioconvergent synthesis of (
R
)‐mandelic ethyl ester catalyze...
Scheme 6.12 Reversible conversion of
N
‐acetyl‐D‐glucosamine to
N
‐acetyl‐D‐ma...
Scheme 6.13 Synthesis of Neu5Ac from GlcNAc with a two‐step enzymatic cascad...
Scheme 6.14 Reversible racemization of D‐ and L‐isomers of 5‐monosubstituted...
Scheme 6.15 The enzymatic cascade reactions for the total conversion of race...
Scheme 6.16 The “double‐racemase hydantoinase process” for optically pure L‐...
Scheme 6.17 Hydantoinase process used for the production of D‐phenylglycine ...
Scheme 6.18 Maleate isomerase catalyzed isomerization of maleic acid to fuma...
Scheme 6.19 Bioconversion of maleic acid into L‐malic acid by consecutive ca...
Scheme 6.20 Linoleate isomerase catalyzed isomerization of
cis
‐9,
cis
‐12‐oct...
Scheme 6.21 The isomerization of either D‐xylose or D‐glucose catalyzed by x...
Scheme 6.22 Hydride shift mechanism of xylose (glucose) isomerase.
Scheme 6.23 Simultaneous isomerization and fermentation of D‐xylose for etha...
Scheme 6.24 Conversion of D‐glucose to D‐psicose by coupling D‐xylose isomer...
Scheme 6.25 Integrated enzyme cascade‐chemocatalytic conversion of cellulose...
Scheme 6.26 D‐Mannitol production by simultaneous enzymatic isomerization an...
Scheme 6.27 L‐Rhamnose isomerase catalyzed reversible isomerization between ...
Scheme 6.28 Production of D‐allose from D‐fructose via D‐psicose by using D‐...
Scheme 6.29 Production of L‐lyxose from ribitol using sequential microbial a...
Scheme 6.30 Two‐step enzymatic synthesis of 6‐deoxy‐L‐psicose from L‐rhamnos...
Scheme 6.31 The isomerization reaction of L‐fucose catalyzed by L‐fucose iso...
Scheme 6.32 Two‐step enzymatic synthesis of L‐fuculose from L‐fucose.
Scheme 6.33 A step‐by‐step coupled enzymatic synthesis of L‐glucose and L‐fr...
Scheme 6.34 Enzyme cascade reactions for the synthesis of L‐fucose analogs....
Scheme 6.35 Structures of L‐fucose and L‐fucose analogs modified at chain te...
Scheme 6.36 Phosphopentomutase catalyzed reversible transfer of a phosphate ...
Scheme 6.37 Biosynthesis of adenosine from ribose 5‐phosphate by immobilized...
Scheme 6.38 Isomerization of D‐xylose 1‐phosphate into D‐xylulose 5‐phosphat...
Scheme 6.39 Enzymatic synthesis of 2’‐deoxyinosine from glucose, acetaldehyd...
Scheme 6.40 One‐pot multistep enzymatic synthesis of thymidine 5’‐diphosphat...
Scheme 6.41 Lysine 2,3‐aminomutase catalyzes the interconversion of L‐lysine...
Scheme 6.42 Chemical structures of tuberactinamine A, tuberactinomycin A, an...
Scheme 6.43 Pathway of
N
ε
‐acetyl‐β‐lysine synthesis in methanogenic arc...
Scheme 6.44 Stereochemical reactions catalyzed by lysine 5,6‐aminomutase....
Scheme 6.45 Reaction of racemic lysine catalyzed by lysine 2,3‐aminomutase a...
Scheme 6.46 Tyrosine 2,3‐aminomutase catalyzed isomerization of L‐tyrosine t...
Scheme 6.47 Biosynthetic pathway for the β‐amino acid moiety of the C‐1027 e...
Scheme 6.48 Biosynthetic pathway for the synthesis of chondramides from L‐ty...
Scheme 6.49 Biosynthesis of (
R
)‐β‐dopa in
C. violaceous
with L‐tyrosine as p...
Scheme 6.50 Phenylalanine aminomutase from
Taxus chinensis
catalyzed L‐α‐phe...
Scheme 6.51 Dynamic kinetic resolution of racemic α‐phenylalanine to yield (
Scheme 6.52 Kinetic resolution of racemic β‐phenylalanine and its derivative...
Scheme 6.53 Conversion of α‐phenylalanine to β‐phenylalanine catalyzed by PA...
Scheme 6.54 Isomerization of L‐phenylalanine to (
S
)‐β‐phenylalanine catalyze...
Scheme 6.55 Isomerization of L‐phenylalanine catalyzed by PAM from
P. fluore
...
Scheme 6.56 Whole‐cell biocatalyst catalyzed substituted α‐phenylalanines to...
Scheme 6.57 L‐Phenylalanine to (
S
)‐β‐phenylalanine catalyzed by the enzyme A...
Scheme 6.58 PAM HitA catalyzed conversion of L‐phenylalanine to (
S
)‐β‐phenyl...
Scheme 6.59 Cyclization of all‐
trans
geranylgeranyl diphosphate to
ent
‐copal...
Scheme 6.60 Conversion from geranylgeranyl diphosphate to
ent
‐kaurene cataly...
Scheme 6.61 Biosynthetic pathways in
S. miltiorrhiza
for gibberellins produc
...
Scheme 6.62 Miltiradiene production from GGPP catalyzed by the fusion of
Sm
C
...
Scheme 6.63 Triptolide production catalyzed by
Tripterygium wilfordii
.
Scheme 6.64 The biosynthesis of defense‐related dolabralexins in maize.
Scheme 6.65 Lycopene β‐cyclase catalyzed conversion of lycopene to β‐caroten...
Scheme 6.66 Carotenoid biosynthetic pathway in higher plants.
Scheme 6.67 Biosynthesis of isorenieratene form β‐carotene via β‐isorenierat...
Scheme 6.68 Biosynthetic pathway of carotene and xanthophyll in
Capsicum
.
Scheme 6.69 Biosynthetic pathway in
P. tricornutum
from β‐carotene to diadin...
Chapter 7
Scheme 7.1 ATP‐dependent olefin β‐lactone synthetase catalyzed β‐lactone for...
Scheme 7.2 Proposed reaction mechanism for the formation of β‐lactone from β...
Scheme 7.3 β‐Lactones formation from β‐hydroxy acids catalyzed by ATP‐depend...
Scheme 7.4 Formation of acetyl‐CoA from acetate, ATP, and CoA catalyzed by a...
Scheme 7.5 Two‐step reaction for the conversion of acetate into acetyl‐CoA c...
Scheme 7.6 Coupled‐enzymatic reactions for citric acid production from oxalo...
Scheme 7.7
In vitro
biosynthesis of poly(3‐hydroxybutyric acid) using cascad...
Scheme 7.8 Simplified metabolic pathways for fatty acids biosynthesis from a...
Scheme 7.9 MACS‐catalyzed two‐step reaction of medium‐chain carboxylate to f...
Scheme 7.10 Glycine conjugation of carboxylic acids catalyzed by MACS and GL...
Scheme 7.11 Biosynthetic pathway for mcl‐PHAs synthesis from 2‐alkenoic acid...
Scheme 7.12 SCL‐
co
‐MCL copolymer production using engineered
E. coli
with in...
Scheme 7.13 Enantioselective thioesterification of racemic CPPA catalyzed by...
Scheme 7.14 (a) Production of butylmalonyl‐CoA from (
E
)‐2‐hexenoyl‐CoA catal...
Scheme 7.15 Biosynthesis of novel terminal‐alkyne‐bearing polyketide startin...
Scheme 7.16 Pathways of JA biosynthesis in plant peroxisomes.
Scheme 7.17 (a) Schematic pathway for the conversion of sucrose to triacylgl...
Scheme 7.18 Acyl‐CoA‐dependent or –independent TAG synthesis pathway derived...
Scheme 7.19 The
de novo
TAG biosynthesis pathway constructed by modification...
Scheme 7.20 Condensation of glutamate and ammonia to generate glutamine cata...
Scheme 7.21 Two primary pathways for glutamate synthesis in
E. coli
.
Scheme 7.22 Biosynthetic pathway of nitrogen assimilation into glutamine, as...
Scheme 7.23 Theanine production by coupling the reaction of GS with glucose ...
Scheme 7.24 Biosynthesis of the antibiotic bacilysin from
L-
alanine and the ...
Scheme 7.25 Hypothesized biosynthetic pathway from prephenate to bacilysin....
Scheme 7.26 Enzymatic production of 2‐amino‐
N
‐(2‐furylmethyl)propanamide (AF...
Scheme 7.27 ATP‐dependent formation of carbapenam‐3‐carboxylate catalyzed by...
Scheme 7.28 Biosynthetic pathway of (5
R
)‐carbapen‐2‐em‐3‐carboxylic acid cat...
Scheme 7.29 CarA catalyzed conversion of three different stereoisomers of 5‐...
Scheme 7.30 Conversion of disubstituted‐5‐CMP derivatives into disubstituted...
Scheme 7.31 Pyruvate carboxylase catalyzed MgATP‐dependent carboxylation of ...
Scheme 7.32 Glucose metabolism in
E. coli
expressed with
R. etli
PYC. (a) Ae...
Scheme 7.33 Central anaerobic metabolic pathway of mutant
E. coli
SBS110MG b...
Scheme 7.34 Anaerobic mixed acid fermentation pathway for
E. coli
. (a) Coexp...
Scheme 7.35 Predominant anaerobic metabolic pathways of
C. glutamicum
for su...
Scheme 7.36 Metabolically engineered
S. cerevisiae
employed for succinate pr...
Scheme 7.37 Major metabolic pathways for the production of malate in
T. glab
...
Scheme 7.38 PMA biosynthesis based on comparative metabolome analysis.
Scheme 7.39 Major metabolic pathways lead to the formation of fumarate I in
Scheme 7.40 Proposed metabolic pathways of propionic acid fermentation with ...
Scheme 7.41 Biosynthetic pathway toward 3‐hydroxypropionic acid from glucose...
Scheme 7.42 Biosynthetic pathway of
L-
lysine via the d,
L-
diaminopimelate int...
Scheme 7.43 Lysine and biotin production using PYC and biotin protein ligase...
Scheme 7.44 Acetyl‐CoA carboxylase catalyzed carboxylation of acetyl‐CoA to ...
Scheme 7.45 Type II fatty acid synthetic pathway. The ACC is a heterotetrame...
Scheme 7.46 Fatty acid metabolic pathway of engineered
E. coli
. Overexpressi...
Scheme 7.47 Engineered
E. coli
for free monounsaturated fatty acid productio...
Scheme 7.48 Simplified principal metabolic pathways for lipid synthesis in
Y
...
Scheme 7.49 Proposed mechanism of SCD‐mediated deregulation of fatty acid pa...
Scheme 7.50 Lipid metabolism of engineered
S. cerevisiae
for fatty alcohol p...
Scheme 7.51 Engineered
E. coli
for production of phloroglucinol from glucose...
Scheme 7.52 Metabolically engineered
S. argillaceus
for production of mithra...
Scheme 7.53 Metabolic pathways of engineered
Y. lipolytica
for TAAL synthesi...
Scheme 7.54 Engineered ethanol‐driven biosynthetic system for production of ...
Scheme 7.55 Biosynthesis of (2
S
)‐flavanones by engineered
E. coli
.
Scheme 7.56 Engineering central metabolic pathways in
E. coli
for plant flav...
Scheme 7.57 Engineered
E. coli
for biosynthesis of 7‐OMA starting from
p
‐cou...
Scheme 7.58 Biosynthesis of 5‐deoxyflavanones in engineered
E. coli
.
Scheme 7.59 Engineered
E. coli
for biosynthesis of 4‐hydroxycoumarin, naring...
Scheme 7.60 Metabolically engineered
S. cerevisiae
for high kaempferol produ...
Scheme 7.61 Modular strategy to optimize biosynthetic pathways in
S. cerevis
...
Scheme 7.62 3‐Hydroxypropionic acid production from glucose through malonyl‐...
Scheme 7.63 Proposed 3‐HP cycle of autotrophic CO
2
fixation in the phototrop...
Scheme 7.64 Biosynthetic pathway of 3‐HP in engineered
Synechocystis
.
Scheme 7.65 Engineered
S. elongatus
with a balanced driving force module for...
Scheme 7.66 3‐HP biosynthetic pathway in engineered
S. cerevisiae
. Bold arro...
Chapter 8
Scheme 8.1 Merrifield’s solid‐phase synthesis of a dipeptide; Cbz, benzyloxy...
Figure 8.1 Split–mix synthesis library in three cycles and each cycle with t...
Scheme 8.2 Removal of the enzyme‐labile urethane protecting group from lipop...
Scheme 8.3 Enzymatic cleavage of (a)
endo
‐ and (b)
oxo
‐linker to release pro...
Figure 8.2 Orthogonality issues in biocatalysis.
Scheme 8.4 Significance of orthogonality on the production of analogues usin...
Scheme 8.5 Iterative synthesis of a 600‐member library from bergenin in two ...
Scheme 8.6 Chemically synthesized combinatorial library of cross‐conjugated ...
Scheme 8.7 Chemoenzymatically library synthesis by Ugi four‐component conden...
Scheme 8.8 Unnatural oligosaccharide library synthesized by using UDP‐Gal an...
Scheme 8.9 Enzymatic synthesis of the glycosylated amino acid derivative bui...
Scheme 8.10 (a) Biosynthesis of Csypyrone B1 with mutant CsyB. (b) Combinato...
Scheme 8.11 Chemical genetic strategy for discovery new macrolide antibiotic...
Scheme 8.12 The precursor‐directed biosynthesis of micacocidin derivatives w...
Scheme 8.13 DhbE catalyzed aryl acid activation and the generation of nonnat...
Scheme 8.14 Triterpene saponin biosynthesis pathway in engineered yeast.
Figure 8.3 Biodegradation pathway for propylene retrieved from the UM‐BBD. (...
Guide
Cover Page
Title Page
Copyright Page
Preface
Acknowledgements
Table of Contents
Begin Reading
Index
Wiley End User License Agreement
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Enzyme‐Based Organic Synthesis
Cheanyeh Cheng
Department of Chemistry
Chung Yuan Christian University
Chungli
Taiwan
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Library of Congress Cataloging‐in‐Publication Data
Names: Cheng, Cheanyeh, author.Title: Enzyme‐based organic synthesis / Cheanyeh Cheng, Department of Chemistry, Chung Yuan Christian University, Chungli, Taiwan.Description: Hoboken, NJ : Wiley, 2022. | Includes bibliographical references and index.Identifiers: LCCN 2021031980 (print) | LCCN 2021031981 (ebook) | ISBN 9781118027943 (hardback) | ISBN 9781118995143 (adobe pdf) | ISBN 9781118995150 (epub)Subjects: LCSH: Enzymes–Synthesis. | Organic compounds–Synthesis. | Biocatalysis. | Enzymes–Biotechnology.Classification: LCC TP248.E5 C44 2021 (print) | LCC TP248.E5 (ebook) | DDC 661/.805–dc23LC record available at https://lccn.loc.gov/2021031980LC ebook record available at https://lccn.loc.gov/2021031981
Cover Design: WileyCover Image: Courtesy of author
Preface
The first time I was introduced to the field of microbiology was during the year 1982–1987, when I studied in the United States in the Department of Chemical & Biochemical Engineering of the Graduate and Professional School of Rutgers University to pursue my PhD degree. I was surprised that bacteria can live in an environment without air and at a temperature much higher than room temperature as well as ferment glucose to acetic acid. This study ignited my interest in the research of microorganisms and enzymes. As soon as I finished my PhD study in 1987, I came back to my alma mater, Chung Yuan Christian University, and worked as an associate professor in the Department of Chemistry, the place where I obtained my BS degree in 1974. I decided to continue my PhD research work to study the enzymatic cellulose hydrolysis for producing glucose using raw materials such as waste paper, dead tree branch, or waste bamboo chopsticks and the enantioselective bioreduction of ketones catalyzed by whole yeast cells for producing chiral secondary alcohols. I also taught a course called bioorganic chemistry, which focuses on the chemo‐, stereo‐, and regioselective enzyme or whole microbial cell catalyzed organic synthesis.
Ten years ago, I received an invitation from Wiley to write this book. At that moment I did not realize it is a big challenge for me to write a comprehensive book concerning enzyme‐catalyzed organic synthesis using six classes of enzymes. With the kind of courage that “the newborn calf is not afraid of tigers,” I accepted this invitation and wrote a book writing proposal. Fortunately, my proposal was approved by reviewers and I immediately started writing this book. Then I found I cannot concentrate my mind on writing this book and it takes me a long time to finish a chapter due to my teaching loads, my research works, student and family affairs, and many other trivial things. In fact, I could put all my time and mind on writing this book only after my retirement from school three and half years ago. I really appreciate the tolerant heart of Wiley editor to allow me to finish this book in such a long time. I learned a lot from writing this book, which also opened a new vision for me in the field of microbes and enzyme‐catalyzed organic synthesis. I also deeply understood the meaning of the Chinese proverb “Live and Learn.” What I did and what knowledge I acquired in my 30 years of academic career is only a small part of the field, just like a drop in the ocean. However, I sincerely hope that through this book more people will be interested in the field of enzyme‐catalyzed organic synthesis.
Life originated from single‐cell microorganisms, and microorganisms that cannot be seen by the human eye have existed on Earth since prehistoric times. Enzymes catalyze diverse chemical reactions in microbial cells from time to time and silently participate in the progress of life. The life phenomena presented by the variety of chemistry involved in the microbial cells is like a solemn and brisk music suite of life. No one would have expected that the relationship between enzymes and the tiny universe of microorganisms is so close and inseparable. Microorganisms are also taken as a cell factory by scientists due to their ability to produce various kinds of useful chemicals for human. However, as a result of the division of labor in science today, chemists, biochemists, biologists, biomedical scientists, biochemical engineers, etc., each use their own specialized scientific expertise to explore this life community, which has led to the difficulty in communication and the inefficient integration among different academic disciplines. Therefore, one of the goals of this book is to enable researchers from different disciplines to communicate and gain consensus to achieve integration.
The difference between enzyme‐based organic synthesis and traditional organic synthesis is that it uses a highly selective biocatalyst (enzyme), and the enzyme selectivity includes reaction substrate specificity, stereospecificity, and regiospecificity. The selectivity of enzyme also makes the enzyme‐based organic synthesis, particularly the asymmetric synthesis, more easy, convenient, and efficient to produce specialty chemicals. Because the enzyme‐based reaction is usually performed in aqueous solution under mild conditions and in many cases using sustainable renewable substrates, which demonstrates environmentally friendly, enzyme‐based organic synthesis fulfils the requirements of green chemistry. The development of enzymatic biotransformation or microbial fermentation has been over 50 years and has been implemented in numerous industrial applications. The recent advances in enzyme technology, such as protein engineering, site‐specific evolution, metabolic engineering, and enzyme immobilization, have made enzyme‐based organic synthesis more and more competitive with organic synthesis derived from fossil fuels.
This book contains eight chapters. Chapter 1 is an introduction to enzyme, coenzyme, enzyme specificity, and the green chemistry. Chapter 2 is about organic syntheses and their applications using class I oxidoreductases. Chapter 3 focuses on the transamination, glycosyl‐transfer, phosphorylation, and acetyl‐group transfer reactions using class II transferases and their applications. Chapter 4 is about class III hydrolases‐based organic syntheses including hydrolysis reactions of ester bond, amide bond, phosphate esters, epoxides, hydantoins, glycosidic bonds with natural polysaccharides, and their applications. Chapter 5 contains organic syntheses and applications using class IV lyases and concentrates on carbon‐carbon bond formation, carbon‐oxygen bond formation, carbon‐nitrogen bond formation, carbon‐sulfur bond formation, and carbon‐halide bond formation. Chapter 6 describes organic syntheses using class V isomerases including racemases and epimerases, cis–trans isomerase, intramolecular oxidoreductases, intramolecular transferases, intramolecular lyases, and their applications. Chapter 7 presents class VI ligases‐based organic syntheses and their applications focusing on carbon‐oxygen bond formation, carbon‐sulfur bond formation, carbon‐nitrogen bond formation, and carbon‐carbon bond formation reactions. The final Chapter 8 shows two major techniques that could assist the advancements of enzyme‐based organic syntheses in the future: one is the combinatorial chemistry and the other is artificial intelligence.
The level of contents of this book is medium to high suitable for readers having some basic knowledge of chemistry, organic chemistry, biochemistry, biology, microbiology, and chemical engineering. This book would be a very good reference book for academic researchers and industrial experts working on research and development. This book could also be used as a textbook for one semester course in senior class or graduate school class. Finally, I hope that this book will be able to “throw a brick to attract jade” to elicit truly outstanding books by experts and scholars in this field.
Cheanyeh ChengChungli, January 2021
Acknowledgements
I would like to thank my parents, Mr. Yet‐Sen Cheng and Mrs. Yen‐In Chen Cheng, for working hard to raise me and for providing me the necessary fees for higher education.
I would like to thank my former teachers and professors for the education they gave me and for inspiring me so that I continue in the academic field and have a good performance.
I would like to thank God for giving me the opportunity to write this book.
