Enzyme-Based Organic Synthesis. Cheanyeh Cheng

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...

      6 Chapter 6Scheme 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 (RScheme 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 SmC...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...

      7 Chapter 7Scheme 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