CHEMICAL ENGINEERING PROCESSES AND APPARATUS FOR THE SYNTHESIS OF COMPOUNDS
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.
1 . A method of producing a compound of Formula II, comprising:
reacting a compound according to Formula III with a compound according to Formula IV in the presence of a geranyl transferase enzyme:
to produce the compound of Formula II;
wherein
R is OH;
R 1 is —COOH;
R 2 is selected from the group consisting of linear or branched CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 6 H 13 , C 7 H 15 and C 8 H 17 ;
R 3 is H;
R 5 is
wherein R 6 is CH 3 ; and
wherein the geranyl transferase enzyme is a GPP olivetolate geranyltransferase.
2 . The method of claim 1 , wherein R 2 is selected from the group consisting of linear CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 6 H 13 , C 7 H 15 and C 8 H 17 .
3 . The method of claim 2 , wherein R 2 is a linear C 3 H 7 group.
4 . The method of claim 1 , further comprising contacting the compound of Formula II with a cannabinoid synthase to obtain a cannabinoid or cannabinoid analog; and
wherein the cannabinoid synthase is selected from the group consisting of a cannabidiolic acid (CBDA) synthase and a tetrahydrocannabinolic acid (THCA) synthase.
5 . The method of claim 4 , wherein the cannabinoid synthase is CBDA synthase.
6 . The method of claim 4 , further comprising isolating the cannabinoid or cannabinoid analog.
7 . The method of claim 4 , further comprising decarboxylating the cannabinoid or cannabinoid analog.
8 . The method of claim 4 , wherein the cannabinoid or cannabinoid analog is a single enantiomer.
9 . The method of claim 4 , wherein the enantiomeric purity of the compound of Formula II is at least 95%.
10 . The method of claim 9 , wherein the enantiomeric purity of the cannabinoid or cannabinoid analog is at least 99%.