Cheanyeh Cheng - Enzyme-Based Organic Synthesis

4 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.

5 Chapter 5Scheme 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 5prod...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...