0.5 h; coproporphyrinogen-III oxidase (from Euglena gracilis);

1: With recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol T=37°C; pH=7; 0.5 h; Inert atmosphereBis-Tris bufferEnzymatic reaction; 2: With dihydrogen peroxide 0.25 h; Bis-Tris buffer;

1.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 0.5 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 1.2: 0.25 h / Bis-Tris buffer 2.1: sodium amalgam; potassium hydroxide / 0.08 h / 80 °C / Darkness 3.1: recombinant oxygen-independent coproporphyrinogen III oxidase; [14C]-Ademetionine; Reduced nicotinamide-adenine dinucleotide; threo-1,4-dimercapto-2,3-butanediol / 1 h / 37 °C / pH 7 / Inert atmosphere; Bis-Tris buffer; Enzymatic reaction 3.2: 0.25 h / Bis-Tris buffer View Scheme

1: With ethylenediaminetetraacetic acid; 1,4-dithio-DL-threitol; uroporphyrinogen decarboxylase in phosphate buffer; water T=37°C; pH=6.8; 2: With ethylenediaminetetraacetic acid; 1,4-dithio-DL-threitol; uroporphyrinogen decarboxylase in phosphate buffer; water T=37°C; 3: With ethylenediaminetetraacetic acid; 1,4-dithio-DL-threitol; uroporphyrinogen decarboxylase in phosphate buffer; water T=37°C; Further stages.;

1: 99 percent / H2 / 10percent Pd/C / tetrahydrofuran 2: 60 percent / trimethyl orthoformate / trifluoroacetic acid / 0.37 h / 0 °C 3: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH2Cl2 / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min 4: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

1: 60 percent / trimethyl orthoformate / trifluoroacetic acid / 0.37 h / 0 °C 2: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH2Cl2 / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min 3: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

1: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH2Cl2 / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min 2: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

1: 80 percent / lead tetra acetate, acetic anhydride / 1 h 2: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 3: H2 / 10percent palladized charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 4: 40 percent / trifluoroacetic acid / 2-3 deg C 70 min, CH2Cl2-CH3OH 18 deg C 2 min 5: 95 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 6: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 7: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

1: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 2: H2 / 10percent palladized charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 3: 40 percent / trifluoroacetic acid / 2-3 deg C 70 min, CH2Cl2-CH3OH 18 deg C 2 min 4: 95 percent / H2 / 10percent palladized charcoal / acetic acid / 4 h / Ambient temperature 5: sodium amalgam, aq. acetic acid / 18 h / 37 °C / enzymes from Euglena gracilis 6: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme

1: 86 percent / sodium benzyl oxide / phenylmethanol / 209 °C 2: 70 percent 3: toluene-p-sulphonic acid / CH2Cl2 / 1.5 h / Ambient temperature 4: 63 percent / H2 / 10percent palladized charcoal / tetrahydrofuran / Ambient temperature 5: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH2Cl2 / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min 6: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min View Scheme