Biosynthesis of substituted compounds and cannabinoids
AssigneeInvizyne Technologies, Inc.
InventorsTyler P. Korman, Bastian Vogeli, Andrew Lingard, Mohammad Hayat
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Abstract
Systems and methods for prenylation and recombinant pathways for the production of compounds, cannabinoids, cannabinoid precursors, and other prenylated chemicals in a cell free system. The present invention further includes enzymes and recombinant microorganisms that catalyze the reaction. The compounds, cannabinoids, cannabinoid precursors, and other prenylated chemicals are operable to be substituted with at least one deuterium, at least one tritium, at least one halogen, at least one hydroxyl group, and/or at least one additional isotope.
Claims20
A cannabinoid composition comprising:
- a cannabinoid derived from a deuterated fatty acid, wherein the cannabinoid is a compound of Formula I:
- wherein R is a deuterated carbon chain;
- and
- wherein the deuterated carbon chain includes at least one deuterated carbon.
A method for synthesizing a cannabinoid compound or derivative thereof, comprising:
- phosphorylating prenol and/or isoprenol using hydroxyethylthiazole kinase (ThiM) to produce isopentenyl phosphate;
- isomerizing isopentenyl phosphate to produce isopentenyl diphosphate, wherein isopentenyl diphosphate is operable to be phosphorylated in the presence of inositol polyphosphate kinase to produce dimethylallyl diphosphate (DMAPP);
- synthesizing geranyl pyrophosphate from isopentenyl diphosphate and/or DMAPP in the presence of farnesyl pyrophosphate synthase;
- activating a deuterated fatty acid to produce a deuterated CoA thioester;
- activating an acid to produce a second CoA thioester;
- synthesizing the deuterated CoA thioester and the second CoA thioester;
- cyclizing the synthesized product to produce a deuterated olivetolic acid;
- prenylating the deuterated olivetolic acid in the presence of geranyl pyrophosphate to produce a deuterated cannabigerolic acid;
- cyclizing the deuterated cannabigerolic acid to produce a deuterated cannabinoid.
A method of cell-free synthesis of a cannabinoid or derivative thereof, comprising:
- cloning at least one polynucleotide sequence encoding at least one enzyme into at least one microorganism to produce a modified microorganism, wherein the modified microorganism exhibits elevated expression of the at least one enzyme in comparison to an unmodified parental microorganism;
- lysing at least one cell of the modified microorganism to obtain the at least one enzyme, wherein the at least one enzyme is used in a cannabinoid biosynthesis pathway;
- producing a cannabinoid or derivative thereof using the cannabinoid biosynthesis pathway, comprising;
- activating a deuterated fatty acid in the presence of an acyl-activating enzyme (AAE) 3 to produce a deuterated CoA thioester, wherein the deuterated fatty acid is a compound of Formula II;
- activating an acid in the presence of a corresponding CoA synthetase to produce a second CoA thioester;
- synthesizing the deuterated CoA thioester and the second CoA thioester in the presence of olivetol synthase (OLS);
- cyclizing the synthesized product in the presence of olivetolic acid cyclase (OAC) to produce a deuterated olivetolic acid;
- prenylating the deuterated olivetolic acid in the presence of geranyl pyrophosphate to produce a deuterated cannabigerolic acid;
- and
- cyclizing the deuterated cannabigerolic acid to produce a deuterated cannabinoid.
Dependencies are inferred from the claim text.