Biotransformation of compounds using non-prokaryotic microalgae
AssigneeTethys Research LLC
InventorNancy G. Kravit
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Abstract
A method for biotransformation of organic compounds using non-prokaryotic microalgae is disclosed. The method is useful to biotransform a chemical precursor compound, preferably a heterocyclic compound, to a chemically distinct final product, which is useful in, e.g., pharmaceutical, agrichemical, nutraceutical, ecological, hazardous waste, food flavoring, or food additive applications.
Claims52
A process for biotransformation of a precursor compound comprising:
- (A) obtaining a panel of different non-prokaryotic microalgae which are evolutionarily and ecologically diverse;
- (B) exposing each member of said panel of non-prokaryotic microalgae to a solvent for the precursor compound, and selecting a subset of non-prokaryotic microalgae that grow in the presence of said solvent;
- (C) exposing each non-prokaryotic microalgae of the resulting subset to the precursor compound, and selecting a further subset of non-prokaryotic microalgae whose growth is inhibited or increased in the presence of said precursor compound;
- (D) growing the resulting further subset of non-prokaryotic microalgae in the presence of said precursor compound so as to transform said precursor compound to produce a metabolite of said precursor compound, and so as to obtain a cellular biomass of said non-prokaryotic microalgae and a culture supernatant;
- (E) separating the resulting cellular biomass from the resulting culture supernatant and optionally extracting the resulting separated cell biomass with said solvent so as to obtain said metabolite of said precursor compound;
- and optionally
- (F) purifying said metabolite from the resulting culture supernatant or solvent extract of the resultant biomass and analyzing said metabolite so as to identify the structure of said metabolite and the modification in said precursor compound.
N1-(tert-butoxycarbonyl)-N1-[1-phenyl(2,3-dihydroxypropyl)methyl]cysteinamide.
S-{2-hydroxy-3-[(tert-butoxycarbonyl)amino]-4-phenylbutyl}cysteine.
A method for preparing N1-(tert-butoxycarbonyl)-N-1-[1-phenyl(2,3-dihydroxypropyl)methyl]cysteinamide, comprising:
- (A) culturing Cryptomonas, in the presence of tert-butyl[S-(R*-R*)]-(−)-(1-oxiranyl-2-phenylethylcarbamate);
- or
- (B) contacting a cell extract of Cryptomonas or enzymes purified therefrom with tert-butyl[S-(R*-R*)]-(−)-(1-oxiranyl-2-phenylethylcarbamate),
- so as to produce N1-(tert-butoxycarbonyl)-N1-[1-phenyl(2,3-dihydroxypropyl)methyl]cysteinamide.
A method for preparing S-{2-hydroxy-3-[(tert-butoxycarbonyl)amino]-4-phenylbutyl}cysteine, comprising:
- (A) culturing Cryptomonas in the presence of tert-butyl[S-(R*-R*)]-(−)-(1-oxiranyl-2-phenylethylcarbamate);
- or
- (B) contacting a cell extract of Cryptomonas or enzymes purified therefrom with tert-butyl[S-(R*-R*)]-(−)-(1-oxiranyl-2-phenylethylcarbamate),
- so as to produce S-{2-hydroxy-3-[(tert-butoxycarbonyl)amino]-4-phenylbutyl}cysteine.
A method for preparing (S)-(−)-3-(Benzyloxycarbonyl)-1-amino-2-hydroxycarboxylic acid, comprising:
- (A) culturing Chlamydomonas in the presence of (S)-(−)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acid;
- or
- (B) contacting a cell extract of Chlamydomonas or enzymes purified therefrom with (S)-(−)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acid,
- so as to produce (S)-(−)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acid.
A method for preparing S-(2-hydroxyethyl) cysteine or a derivative thereof containing substitutions in the ethyl group, comprising:
- (A) culturing Cryptomonas in the presence of oxirane or a 2-substituted derivative thereof, or
- (B) contacting a cell extract of Cryptomonas or enzymes purified therefrom with 2-oxirane or a 2-substituted derivative thereof,
- so as to produce S-(2-hydroxyethyl)cysteine or a derivative thereof containing substitutions in the ethyl group.
Dependencies are inferred from the claim text.