Chemical engineering processes and apparatus for the synthesis of compounds
AssigneeTeewinot Technologies Limited
InventorsRichard PEET, Malcolm J. KAVARANA, Robert WINNICKI, Marc DONSKY, Mingyang SUN
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Abstract
The present invention provides methods for producing cannabinoids and cannabinoid analogs as well as a system for producing these compounds. The inventive method is directed to contacting a compound according to Formula I or Formula II with a cannabinoid synthase. Also described is a system for producing cannabinoids and cannabinoid analogs by contacting a THCA synthase with a cannabinoid precursor and modifying at least one property of the reaction mixture to influence the quantity formed of a first cannabinoid relative to the quantity formed of a second cannabinoid.
Claims20
A system for producing cannabinoid products, comprising:
- a fermentor holding a cell culture medium comprising genetically engineered yeast or bacterial cells that are (a) producing a cannabinoid synthase selected from the group consisting of tetrahydrocannabinolic acid (THCA) synthase and cannabidiolic acid (CBDA) synthase and (b) secreting the cannabinoid synthase into the culture medium;
- and
- a bioreactor containing a reaction mixture comprising the cannabinoid synthase and 3-(3,7-dimethylocta-2,6-diene-1-yl)-2,4-dihydroxy-6-propyl-1-benzoic acid (CBGVA) and configured to form one or more cannabinoid products.
A method for producing a tetrahydrocannabinol, cannabichromene, or both tetrahydrocannabinol and cannabichromene, or their analogs comprising the steps of:
- (a) selecting a compound according to Formula V:
- (b) reacting the Formula V compound with THCA synthase in the presence of a solvent;
- (c) modifying at least one property of a reaction mixture comprising the Formula V compound and THCA synthase to obtain a tetrahydrocannabinol, a cannabichromene, or both tetrahydrocannabinol and cannabichromene, or their analogs as products;
- wherein
- R is selected from —OH, halogen, —SH, or a —NRaRb group;
- R1 and R2 are each independently selected from the group consisting of —H, —C(O)Ra, —ORa, an optionally substituted C1-C10 linear or branched alkylene, an optionally substituted C2-C10 linear or branched alkenylene, an optionally substituted C2-C10 linear or branched alkynylene, an optionally substituted C3-C10 aryl, an optionally substituted C3-C10 cycloalkyl, (C3-C10)aryl-(C1-C10)alkylene, (C3-C10)aryl-(C2-C10)alkenylene, and (C3-C10)aryl-(C1-C10)alkynylene, or
- R1 and R2 together with the carbon atoms to which they are bonded form a C5-C10 cyclic ring;
- R3 is selected from the group consisting of H, —C(O)Ra, and C1-C10 linear or branched alkyl;
- and
- Ra and Rb are each independently selected from the group consisting of —H. —OH, —SH, —NH2, (C1-C10) linear or branched alkyl, and a C3-C10 cycloalkyl.
A method for optimizing production of one or more cannabinoids comprising:
- (a) cloning cannabinoid synthases from multiple sources into host cells, expressing the cannabinoid synthases in the host cells, and isolating the cannabinoid synthases from the host cells;
- (b) determining the catalytic activity of each of the isolated cannabinoid synthases and comparing the catalytic activities to identify an optimal cannabinoid synthase having a high catalytic activity;
- (c) inserting multiple copies of the optimal cannabinoid synthase into an expression vector;
- (d) transforming a host cell with the expression vector obtained in step (c), expressing the optimal cannabinoid synthase in the transformed host cell, and isolating the optimal cannabinoid synthase from the transformed host cell;
- and
- (e) reacting cannabigerolic acid (CBGA) or CBGVA with the optimal cannabinoid synthase isolated in step (d) in a reaction mixture to produce one or more cannabinoids;
- wherein the optimal cannabinoid synthase is a CBDA synthase or a THCA synthase, and wherein the reaction mixture comprises one or more solvents of DMSO, DMF, iso-propyl alcohol, and cyclodextrin.
Dependencies are inferred from the claim text.