No description available.

The purpose of this research was to synthesize 7-bromodeaminolavendamycin methyl ester (11), deaminolavendamycin methyl ester (19), 7-N-isobutyryldemethyllavendamycin methyl ester (54), 7-N-acetyldemethyllavendamycin ethyl ester (64), 7-Nisobutyryldemethyllavendamycin butyl ester (76), 7-N-isobutyryldemethyllavendamycin tbutyl ester (78), 7-N-cetyldemethyllavendamycin phenyl ester(79), and 7-Nisobutyryldemethyllavendamycin isopropyl ester (80).Lavendamycins 54, 64, 76, 80 were synthesized via the Pictet-Spengler condensation of the corresponding tryptophan esters with 7-N-acetamido-2-formylquinolinedione (91) or 7-N-isobutyramido-2-formylquinolinedione (92). 3-Carbomethoxy-l-( 8-hydroxyquinoline2-yl )-4-methyl-(3-carboline (18), and 3-carbomethoxy-l-(5-acetamido-8-acetoxy-7bromo-2-yl)-4-methyl-(3-carboline (109) were also prepared through the Pictet-Spengler condensation of p-methyl tryptophan methyl ester with 2-formyl-8-hydroxyquinoline (103) and 5-acetamido-8-acetoxy-7-bromo-2-formylquinoline (108), respectively.Compounds 18 and 109 were oxidized by potassium dichromate or Fremy's salt to give deaminolavendamycin methyl ester (19) and 7-bromodeaminolavendamycin methyl ester (11) respectively.7-Isobutyramido-2-formylquinoline-5,8-dione (92) was prepared according to the following general procedure. 8-Hydroxy-2-methylquinoline (26) was reacted with a 70% mixture of HNO3 / H2SO4 to produce 8-hydroxy-2-methyl-5,7-dinitroquinoline (39). Compound 39 was reduced by H2 / Pd-C and then reacted with isobutyric anhydride in the presence of sodium sulfite and sodium acetate to produce 88. Recrystallization of 88 with methanol gave 5,7-diisobutyramido-8-hydroxy-2-methylquinoline (98). Compound 98 was suspended in acetic acid and oxidized by a solution of potassium dichromate to give 7isobutyramido-2-methylquinoline-5,8-dione (90). The dione derivative 90 was oxidized by selenium dioxide in 1,4-dioxane to yield the target aldehyde 92. 2-Formyl-8hydroxyquinoline (103) was synthesized through a selenium dioxide oxidation of 8hydroxy-2-methylquinoline (26).Ester 96 was prepared by the Fischer esterification of L-tryptophan with an excess amount of isopropyl alcohol in the presence of dry HCI. L-Tryptophan phenyl ester (97) was prepared through a two-step reaction. NCBZ-L-tryptophan (101) was treated with phenol and BOP reagent in the presence of triethylamine in acetonitrile to yield NCBZ-L tryptophan phenyl ester (102). The N-protected ester was reduced to L-tryptophan phenyl ester (97) by ammonium formate in the presence of palladium on charcoal in N,Ndimethylformamide. Esters 93-95 were obtained by the treatment of their commercially available hydrochloride salts with 14% NH4OH and then extraction with ethyl acetate.The structures of the compounds 11, 18, 19, 54, 64, 76, 80, 88, 90, 92, 96, 97, 98, 102, 103, 106, 108 and 109 were comfirmed through tH NMR, IR, and MS. Elemental analyses of 90, 92, 96, 98, 103 and 106 and HRMS of 98, 19, 54, 76, 95, 109 are also included. 1H NMR are also provided for compounds 39, 94,95. / Department of Chemistry

The synthesis of 7-acetyl-11'-benzyloxylavendamycin methyl ester (47), 7acetyl-11'-hydroxylavendamycin methyl ester (48), 11'-hydroxylavendamycin methyl ester (49), 11'-benzyloxylavendamycin methyl ester (50), are described. Pictet-Spengler condensation of 7-N-acetyl-2-formylquinoline-5,8-dione (26) with 5-benzyloxytrytophan methyl ester (45) or 5-hydroxytryptophan methyl ester (46) in dry xylene or anisole directly afforded lavendamycin analogs 47 or 48. Compound 49 was obtained by hydrolysis of 48 with 70% H2SO4 - H2Osolution. Compound 50 was obtained by hydrolysis of 47 with sodium carbonate solution.Aldehyde 26 was prepared according to the following general procedure. Nitration of 8-hydroxy-2-methylquinoline (28) yielded 8-hydroxy-2-methyl5,7-dinitroquinoline (29). Compound 29 was then hydrogenated and acylated with acetic anhydride to yield 5,7-bis(diacetamido)-8-hydroxy-2methylquinoline (31). Compound 31 was oxidized to give 5,8- dione 25 by using potassium dichromate. Treatment of compound 25 with selenium dioxide in refluxing 1,4-dioxane yielded compound 26.3 (Isopropylaminoethylidene)-6,7-dimethoxyindole (39) was prepared via the following procedure. Acylation of vanillin (32) with acetic anhydride yielded acetylvanillin (33). Compound 33 was nitrated and hydrolyzed to give 2nitrovanillin (35). Compound 35 was then methylated using dimethyl sulfate to produce 2-nitroveratric aldehyde (36). Condensation of compound 36 with nitromethane yielded 3,4-dimethoxy-2-f3-nitrostyrene (37). Ammonium formate reductive cyclization of compound 37 in refluxing methanol in the presence of a catalytic amount of 10% palladium on charcoal yielded 6,7dimethoxyindole (38). Electrophilic substitution reaction of compound 38 with ethylideneisopropylamine (41) in dry toluene yielded compound 39.Methyl (2RS, 3SR)-2-amino-3-[3-(5-benzyloxyindolyl)]butanoate (45) and methyl (2RS, 3SR)-2-amino-3-[3-(5-hydroxyindolyl)]butanoate (46) were obtained following the procedure described below. Electrophilic substitutionreaction of 5-bezyloxyindole (40) with ethylideneisopropylamine (41) in dry toluene yielded 3-(isopropylaminoethylidene)-5-benzyloxyindole (42). Condensation of compound 42 with methyl nitroacetate (43) in dry toluene gave methyl 3-[3-(5-benzyloxyindolyl)]3-nitrobutanoate (44). Hydrogenation of compound 44 in the presence of Raney nickel and trifluoroacetic acid in ethanol yielded methyl (2RS, 3SR)-2-amino-3-[3-(5-benzyloxyindolyl)] butanoate (45). Hydrogenation of compound 44 in the presence of 10% palladium on charcoal and trifluoroacetic acid in ethanol yielded methyl (2RS, 3SR)-2-amino-3-[3-(5-hydroxyindolyl)] butanoate (46).The structures of the novel compounds were confirmed by 1H NMR, IR, and HRMS or elemental analysis. / Department of Chemistry

There is no abstract available for this thesis. / Department of Chemistry

The synthesis of several 7-substituted analogs of 2-methylquinoline-5,8-dione and their chemistry are described. In this investigation the following compounds were prepared.5,7-Diformamido-8-hydroxy-2-methylquinoline (207), 7-formamido-2methylquinoline-5,8-dione (199), 7-acetamido-2-methylquinoline-5,8-dione (6), 7-isobutyramido-2-methylquinoline-5,8-dione (200), 7-amino-2-methylquinoline-5,8-dione (210), 7-amino-6-chloro-2-methylquinoline-5,8-dione (213), 7-methoxy-2-methylquinoline5,8-dione (214), 7-ethoxy-2-methylquinoline-5,8-dione (215), 7-isopropyloxy-2methylquinoline-5,8-dione (216), 7-amino-5-ethyl-5-hydroxy-2-methylquinoline-8-one (218), 7-acetamido-5-ethyl-5-hydroxy-2-methylquinoline-8-one (220), and 7-chloro-2methylquinoline-5,8-dione (222).Trimetylacetic formic anhydride (206) was prepared according to McGarvy,s 68 method from treatment of sodium formate (204) and trimethylacetyl chloride (203) in the presence of poly (4-vinylpyridine-N-oxide) (205) as catalyst. 7-Formamido-2methylquinoline-5,8-dione (199) was prepared according to the following general procedure. 8-Hydroxy-2-mehylquinoline (5) was reacted with a 70% mixture of HNO3/H2SO4 to produce 5,7-dinitro-8-hydroxy-2-methylquinoline (18). Compound 18 was reduced by H2/Pd-C in the presence of HCl and then the resulting 5,7-diamino-8-hydroxy-2 methylquinolin-5,8-dione hydrochloride salt (198) reacted with trimethylacetic formic anhydride to produce 5,7-diformamido-8-hydroxy-2-methylquinoline-5,8-dione (207). Compound 207 was treated with a solution of potassium dichromate in acetic acid-water mixture to give product 199.7-Acetamido-2-methylquinoline-5,8-dione (6) was prepared from reaction of a solution of 198 with acetic anhydride in the presence of sodium acetate and sodium sulfite followed by oxidation with potassium dichromate in acetic acid-water solution. 7-Isobutyramido-2methylquinoline-5,8-dione (200) was prepared according to following procedure. Treatment of a solution of 198 with isobutyric anhydride in the presence of sodium acetate and sodium sulfite afforded 5,7-diisobutyramido-8-isobutyroxy-2-methylquinoline (212). Partial hydrolysis of 212 in boiling methanol-water mixture gave 5,7-diisobutyramido-8-hydroxy-2methylquinoline (211). Oxidation of 211 by a solution of potassium dichromate in acetic acid-water mixture afforded product 200.7-amino-2-methylquinoline-5,8-dione (210) was prepared from alcoholysis of 7-acylamino-2-methylquinoline-5,8-diones 6, 199,and 200 with methanol and sulfuric acid. 7-Alkoxy-2-methylquinoline-5,8-diones 214, 215, and 216 were prepared from reaction of 7-acetamido compound 6 with alcohols in the presence of sulfuric acid. Reaction of 7-acylamino compounds 6, 199, and 200 with methanol in the presence of hydrogen chloride gas at 60°C afforded 7-amino-6-chloro-2-methylquinoline-5,8-dione (213).Reaction of compound 210 with diethylaluminum cyanide gave 7-amino-5-ethyl-5hydroxy-2-methylquinoline-8-one (218). The same reaction was carried out on compound 6 to give 7-acetamido-5-ethyl-5-hydroxy-2-methylquinoline-8-one (220).1-[(tert-Butyldimethylsilyl)oxy]-2-methyl-l-aza-1,3-butadiene (4) was prepared from treatment of methyl vinyl ketone (210) and t-butylmethylsilylhydroxylamine (202) in dichloromethane in the presence of molecular sieves. Cycloaddition reaction of a solution of 4 in dichloromethane with 2,6-dichloro-1,4-benzoquinone (221) in sealed tube afforded 7-chloro-2-methylquinoline-5,8-dione (222). / Department of Chemistry

The synthesis of 7-N -furoyllavendamycin methyl ester (35), 7-N -furoyl demethyllavendamycin methyl ester (36), 7-N -furoyldemethyllavendamycin ethyl ester (37), 7-N -furoyldemethyllavendamycin propyl ester (38), 7-N -furoyl demethyl lavendamycin butyl ester (39), 7-N -furoyldemethyllavendamycin isoamyl ester (40),7-N -furoyldemethyllavendamycin cyclohexyl ester (41), 7-N -furoyldemethyl lavendamycin octyl ester (42), 7-N -furoyldecarboxydemethyllavendamycin (43), and demethyl lavendamycin isoamyl ester (44) are described. Pictet-Spengler condensation of 7-furoylamino-2-formylquinoline-5, 8-dione (55) with (3-methyltryptophan methyl ester (4), Ltryptophan methyl ester (56), L-tryptophan ethyl ester (57), L-tryptophan propyl ester (58), L-tryptophan butyl ester (59), L-tryptophan isoamyl ester (60), L-tryptophan cyclohexyl ester (61), L-tryptophan octyl ester (62), L-tryptamine (63), in xylene, or anisole afforded ten lavendamycin analogs.Aldehyde 55 was prepared according to the following general procedure.Nitration of 8-hydroxy-2-methylquinoline (30) gave 8-hydroxy-2-methyl-5,7dinitroquinoline (31). Compound 31 was then hydrogenated and acylated with 2-furoyl chloride (or acetic anhydride ) to yield 5,7-difuroylamino-8-hydroxy-2-methylquinoline (53) or 5,7-diacetamino-8-acetoxy-2-methyl- quinoline (33). Compounds 53 and 33 were oxidized by potassium dichromate to give the corresponding 5,8-diones 54, and 27. Treatment of 53, and 27 with selenium dioxide in refluxing wet dioxane afforded compounds 55 and 28.Compound 4 was previously prepared by other members of our group, compounds 56, 57, 59, and 62 were obtained through the neutralization of the corresponding Ltryptophan ester hydrochlorides with a 14% ammonium hydroxide solution followed by extraction. Compounds 58, 60, 61 were synthesized via a Fischer esterification of Ltryptophan with : propyl alcohol, isoamyl alcohol, and cyclohexyl alcohol saturated with hydrogen chloride.The structures of compounds 53, 54, 55, 35, 36, 37, 38, 39, 40, 41, 42, 43, and 44 were confirmed through 1H NMR, IR, EIMS, and HRMS. Elemental analyses of 53, 54, and 55 are also included.The structures of esters 56, 57, 58, 59, 60, 61, 62, and 63 were confirmed by 1H NMR. / Department of Chemistry

The synthesis of 7-N-acetyldemethyllavendamycin butyl amide (47), 7-Nacetyldemethyllavendamycin isopropyl amide (48), 7-N-acetyldemethyllavendamycin amide of piperidine (49), 7-N-acetyldemethyllavendamycin amide of pyrrolidine (50), 7N-acetyldemethyllavendamycin amide of morpholine (51), demethyllavendamycin butyl amide (52), demethyllavendamycin amide of pyrrolidine (53), and demethyllavendamycin amide of morpholine (54) are described. Pictet Spengler condesation of 7-acetamido-2formylquinoline-5,8-dione (28) with tryptophan butyl amide (66), tryptophan isopropyl amide (67), tryptophan amide of piperidine (68), tryptophan amide of pyrrolidine (69), and tryptophan amide of morpholine (70) in an anisole - pyridine solution directly afforded the five lavendamycin amides 47-51. Compounds 52, 53, and 54 were obtained by hydrolysis of 47, 50, and 51 with 70% H2SO4-H20 solution.Aldehyde 28 was prepared according to the following general procedure.Nitration of 8-hydroxy-2-methylquinoline (30) yielded 8-hydroxy-2-methyl-5,7 dinitroquinoline (31). Compound 31 was then hydrogenated and acylated with acetic anhydride to yield 5,7-diacetamido-2-methyl-8-acetoxyquinoline (33). Compound 33 was oxidized by potassium dichromate to give 7-acetamido-2-methylquinoline-5,8-dione (27). Treatment of 27 with selenium dioxide in refluxing 1,4-dioxane afforded compound 28.Compounds 66, 67, 68, 69, and 70 were synthesized from compounds 61,62, 63, 64, and 65. These compounds were deprotected with ammonium formate in the presence of 10% Palladium on charcoal in methanol under an argon balloon at atmospheric pressure.Compounds 61, 62, 63, 64, and 65 were obtained from 58 with butylamine, isopropylamine, piperidine, pyrrolidine, and morpholine respectively in the presence of triethylamine under an argon balloon at atmospheric pressure.Compound 58 was synthesized by the reaction of N-carbobenzyloxytryptophan, with N-hydroxy succinimide, in the presence of N-dicyclohexylcarbodimide in dried and distilled dioxane under an argon balloon at atmospheric pressure.The structures of the novel compounds 58, 47, 48, 49, 50, 51, 52, 53, and 54 were confirmed by 1H NMR, IR, EIMS, and HRMS.The structures of protected and deprotected amides 61, 62, 63, 64, 65, 66, 67, 68, 69, and 70 were also confirmed by 1 H NMR and IR spectroscopy. / Department of Chemistry

This thesis investigates the use of arene chromium complexes as phenyl cation synthons in the synthesis of homochiral N-phenylamino esters, and the dianion formation of a series of complexed aryl ethers. Chapter 1 reviews the properties of arene chromium tricarbonyl complexes and discusses in detail the ability of some of these complexes to undergo nucleophilic aromatic substitution. Chapter 2 outlines the biological importance of homochiral N-phenylamino esters. The N-phenylation of a series of amino alcohols are first investigated both by direct reaction of haloarene complexes with amino alcohols and also via a Smiles rearrangement of an aryl ether derivative. In addition, methodology is developed for the synthesis of a series of homochiral N-phenyl-α-amino esters and N-phenyl-β-amino esters. The synthetic strategy is then applied to the synthesis of some N-phenyl-β-lactams, in particular (+)SCH 48461. Chapter 3 reviews the directed metallation of complexed and uncomplexed arene compounds and discusses the mechanism involved. The generation of dianions in a series of complexed aryl ethers is investigated. Regioselective deprotonation is observed using different alkyllithium bases and the degree of dianion formation is confirmed by electrophilic quench of the dianionic intermediates with CD₃OD and TMSC1.

Several camphor and pinane derivatives have been synthesised and evaluated for use as chiral auxiliaries in asymmetric synthesis. Various blocking groups have been attached to the camphor skeleton in attempts to improve stereofacial selectivity; these include α-methoxybenzyl and xylyl groups, and novel stereoisomeric ketal moieties derived from meso- and (R,R)-(-)-2,3-butanediol. Benzylation reactions carried out on the lithium enolates of ester derivatives of the camphor-derived chiral auxiliaries afforded α-benzylated products in 5-60% diastereomeric excess. Stereochemical aspects have been explored using high resolution NMR, X-ray crystallographic and computer modelling techniques, and hydrolysis of selected α-benzylated products has permitted the diasteroselective bias to be confirmed. Opposite configurations at the new stereogenic centre are clearly favoured by the xylyl and ketal blocking groups - an observation rationalised in terms of the presence or absence of chelating potential in the blocking group. Baylis-Hillman reactions carried out on a series of specially prepared camphor-derived acrylic esters containing the ketal blocking group exhibited both low diastereoselectivities (0-30% d.e.) and very long reaction times. Chiral silyl enol ethers, synthesised using both pinane and camphor derivatives as chiral auxiliaries, showed up to 20% diastereomeric excess in MCPBA oxidation, alkylation and Mukaiyama reactions. Attempts to bring the prochiral centre in the silyl enol ether substrates closer to the chiral auxiliary, and thus improve the stereofacial selectivity, proved unsuccessful. The silyl enol ether derivatives, however, display interesting fragmentation patterns in their electron impact mass spectra, which were investigated using a combination of high resolution MS, comparative low resolution MS and metastable peak analysis.

Kam, Shuk Fan. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2009. / Includes bibliographical references (leaves 124-134). / Abstracts in English and Chinese. / Abstract --- p.ii / Abstract in Chinese --- p.iv / Acknowledgements --- p.vi / List of Figures --- p.xi / List of Tables --- p.xii / Chapter Chapter 1 --- Literature Review --- p.1 / Chapter 1.1 --- Soybeans as Food --- p.1 / Chapter 1.1.1 --- Backgrounds --- p.1 / Chapter 1.1.2 --- Soybean Composition --- p.1 / Chapter 1.1.3 --- Diseases Prevention of Soybean Consumption --- p.3 / Chapter 1.1.4 --- Traditional Soyfoods --- p.3 / Chapter 1.2 --- Sufu --- p.5 / Chapter 1.2.1 --- Historical Information and Synonyms --- p.5 / Chapter 1.2.2 --- Features --- p.5 / Chapter 1.2.3 --- Manufacturing Techniques --- p.5 / Chapter 1.2.4 --- Types and Varieties of Sufu --- p.10 / Chapter 1.2.5 --- Compositional Changes during Fermentation and Ripening --- p.11 / Chapter 1.2.5.1 --- Proteins and Amino Acids --- p.11 / Chapter 1.2.5.2 --- Fats and Free Fatty Acids --- p.13 / Chapter 1.2.5.3 --- Carbohydrates --- p.14 / Chapter 1.2.5.4 --- Isoflavones --- p.15 / Chapter 1.2.6 --- Volatile Flavor Compounds --- p.15 / Chapter 1.3 --- Accelerated-Ripened Sufu --- p.17 / Chapter 1.4 --- Objectives of Project --- p.18 / Chapter Chapter 2 --- Contribution of Lipid to the Fatty Acids and Ethyl Esters in Model Plain Sufu --- p.20 / Chapter 2.1 --- Introduction --- p.20 / Chapter 2.2 --- Materials and Methodology --- p.23 / Chapter 2.2.1 --- Sufu Preparation --- p.23 / Chapter 2.2.1.1 --- Preparation of Tofu --- p.23 / Chapter 2.2.1.2 --- Preparation of Inoculum --- p.23 / Chapter 2.2.1.3 --- Spore Count in Spore Suspension --- p.24 / Chapter 2.2.1.4 --- Preparation of Pehtzes --- p.25 / Chapter 2.2.1.5 --- Brining and Ripening --- p.26 / Chapter 2.2.1.6 --- Sampling --- p.26 / Chapter 2.2.1.7 --- Free Fatty Acid Analysis --- p.26 / Chapter 2.2.1.7.1 --- Extraction --- p.26 / Chapter 2.2.1.7.2 --- Gas Chromatography-Mass Spectrometry Analysis (GC-MS) for Free Fatty Acid Analysis --- p.27 / Chapter 2.2.1.7.3 --- Compounds Identification and Quantification --- p.28 / Chapter 2.2.1.8 --- Ethyl Ester Analysis --- p.29 / Chapter 2.2.1.8.1 --- Extraction --- p.29 / Chapter 2.2.1.8.2 --- Gas Chromatography-Mass Spectrometry Analysis (GC-MS) for Ethyl Ester Analysis --- p.29 / Chapter 2.2.1.8.3 --- Compounds Identification and Quantification --- p.30 / Chapter 2.2.1.9 --- Enzymatic Activities --- p.30 / Chapter 2.2.1.9.1 --- Enzyme Extracts --- p.30 / Chapter 2.2.1.9.2 --- Lipase Activity Measurement --- p.31 / Chapter 2.2.1.9.3 --- Lipoxygenase Activity Measurement --- p.32 / Chapter 2.2.1.10 --- Determination of Peroxide Value --- p.33 / Chapter 2.2.1.11 --- pH Value Determination --- p.34 / Chapter 2.2.1.12 --- Moisture Content --- p.34 / Chapter 2.2.1.13 --- Statistical Analysis --- p.34 / Chapter 2.3 --- Results and Discussions --- p.35 / Chapter 2.3.1 --- Change of Free Fatty Acids with Sufu Processing Stage --- p.35 / Chapter 2.3.2 --- Change in Ethyl Esters with Sufu Processing Stage --- p.41 / Chapter 2.3.3 --- Activity of Lipase in the Sufu Enzyme Extracts --- p.47 / Chapter 2.3.4 --- Activity of Lipoxygenase in the Sufu Enzyme Extracts --- p.50 / Chapter 2.3.5 --- Lipid Oxidation determined by Peroxide Value --- p.50 / Chapter 2.3.6 --- pH Value Change during Sufu Production --- p.54 / Chapter 2.3.7 --- Moisture Content during Sufu Production --- p.56 / Chapter 2.3.8 --- Overall Discussions --- p.58 / Chapter 2.3.8.1 --- Lipolysis and Ester Synthesis --- p.58 / Chapter 2.3.8.2 --- Lipid Oxidation --- p.58 / Chapter 2.4 --- Conclusion --- p.61 / Chapter Chapter 3 --- A Study on Ripening Model Systems of Sufu --- p.63 / Chapter 3.1 --- Introduction --- p.63 / Chapter 3.2 --- Materials and Methodology --- p.68 / Chapter 3.2.1 --- Partial Purification Lipase from Mucor hiemalis --- p.68 / Chapter 3.2.1.1 --- Inoculum --- p.68 / Chapter 3.2.1.2 --- Culture --- p.68 / Chapter 3.2.1.3 --- Protein Precipitation --- p.68 / Chapter 3.2.1.4 --- Gel Filtration Column Chromatography --- p.69 / Chapter 3.2.1.5 --- Enzyme Assay --- p.69 / Chapter 3.2.1.6 --- Lipase Activity Confirmation --- p.70 / Chapter 3.2.1.7 --- Protein Determination --- p.70 / Chapter 3.2.2 --- Model Studies of the Formation of Free Fatty Acids and Ethyl Esters --- p.70 / Chapter 3.2.2.1 --- "A System with Lipid, Alcohol, and Lipase" --- p.70 / Chapter 3.2.2.2 --- A System with Different Lipase Concentrations --- p.71 / Chapter 3.2.2.3 --- A System with an Exogenous Fatty Acid --- p.71 / Chapter 3.2.3 --- Characterization of the Crude Lipase from Mucor hiemalis Culture on the Formation of Free Fatty Acids and their Ethyl Esters --- p.72 / Chapter 3.2.3.1 --- Effect of a Phospholipid --- p.72 / Chapter 3.2.3.2 --- Effect of Ethanol Concentration --- p.72 / Chapter 3.2.3.3 --- Effect of Sodium Chloride Concentration --- p.72 / Chapter 3.2.3.4 --- Effect of initial pH --- p.73 / Chapter 3.2.4 --- Orthogonal Design Experiment L9 (33) --- p.73 / Chapter 3.2.5 --- Free Fatty Acids Identification and Quantification --- p.76 / Chapter 3.2.5.1 --- Extraction --- p.76 / Chapter 3.2.5.2 --- Gas Chromatography-Mass Spectrometry Analysis (GC-MS) --- p.76 / Chapter 3.2.5.3 --- Compounds Identification and Quantification --- p.77 / Chapter 3.2.6 --- Ethyl Esters Identification and Quantification --- p.77 / Chapter 3.2.6.1 --- Extraction --- p.77 / Chapter 3.2.6.2 --- Gas Chromatography-Mass Spectrometry Analysis (GC-MS) --- p.78 / Chapter 3.2.6.3 --- Compounds Identification and Quantification --- p.78 / Chapter 3.2.7 --- Statistical Analysis --- p.79 / Chapter 3.3 --- Results and Discussions --- p.80 / Chapter 3.3.1 --- Lipase Partial Purification --- p.80 / Chapter 3.3.2 --- Lipase Activity Confirmation --- p.80 / Chapter 3.3.3 --- Model Studies on the Formation of Free Fatty Acids and Ethyl Esters --- p.84 / Chapter 3.3.3.1 --- "A System with Lipid, Alcohol and Lipase" --- p.84 / Chapter 3.3.3.2 --- A System with Different Lipase Concentrations --- p.84 / Chapter 3.3.3.3 --- A System with an Exogenous Fatty Acid --- p.89 / Chapter 3.3.3.4 --- Summary --- p.92 / Chapter 3.3.4 --- Characterization of the Crude Lipase from Mucor hiemalis Culture on the Formation of Free Fatty Acids and their Ethyl Esters Formation --- p.92 / Chapter 3.3.4.1 --- Effect of a Phospholipid --- p.92 / Chapter 3.3.4.2 --- Effect of Ethanol Concentration --- p.96 / Chapter 3.3.4.3 --- Effect of Sodium Chloride Concentration --- p.103 / Chapter 3.3.4.4 --- Effect of initial pH --- p.109 / Chapter 3.3.5 --- Orthogonal Design Experiment L9 (33) Optimizing the Ethyl Esters Formation --- p.114 / Chapter 3.4 --- Conclusion --- p.118 / Chapter 4 Overall Conclusions --- p.120 / References --- p.124