Enzyme-Based Organic Synthesis. Cheanyeh Cheng

Figure 1.3 The stereospecificity of enzyme for two substrate enantiomers by ...Scheme 1.4 Enantioselective synthesis of (3aS,6aR)‐lactone.Scheme 1.5 The enantioselective conversion of HPMAE to (S)‐phenylephrine....Scheme 1.6 Regio‐ and stereoselective concurrent oxidations of racemic vicin...

      2 Chapter 2Scheme 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 pScheme 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...

      3 Chapter 3Scheme 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