Biosynthesis of cyclolavandulyl derivatives of aromatic compounds
AssigneeInvizyne Technologies, Inc.
InventorsJohn BILLINGSLEY, Tyler P. KORMAN, Mohammad HAYAT
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Abstract
The present disclosure relates to compositions comprising cyclolavandulyl derivatives of aromatic compounds, such as cannabinoids, flavonoids, and alkaloids, and methods for preparing and using the compositions.
Claims40
A compound of structural formula (Ia) or (Ib):
- wherein, R1 is selected from
- wherein,
- R2 is —H or —OH;
- R3 is —H or —COOH;
- and
- R4 is —H, —OH, linear or branched C1-C10 alkyl, linear or branched C1-C10 alkyl-amide, linear or branched C1-C10 alkyl-amine, linear or branched C1-C10 alkyl-alkylene, linear or branched C1-C10 alkyl-alkoxy, or C1-C10 alkyl-aryl, wherein any of the C1-C10 groups is optionally substituted with —OH, —OCH3, or halogen.
A method for preparing a cyclolavandulyl-substituted aromatic compound comprising:
- (a) contacting under suitable reaction conditions:
- a prenyitransferase, a cyclolavandulyl pyrophosphate of compound (1)
- and an aromatic compound selected from a compound of structural formulas (II), (MV), (V), and (VI)
- wherein,
- R2 is —H or —OH;
- R3 is —H or —COOH;
- and
- R4 is —H, —OH, linear or branched C1-C10 alkyl, linear or branched C1-C10 alkyl-amide, linear or branched C1-C10 alkyl-amine, linear or branched C1-C10 alkyl-alkylene, linear or branched C1-C10 alkyl-alkoxy, or C1-C10 alkyl-aryl, wherein any of the C1-C10 groups is optionally substituted with —OH, —OCH3, or halogen;
- and
- (b) recovering the cyclolavandulyl-substituted aromatic compound from the reaction mixture.
A composition comprising a prenyltransferase, a cyclolavandulyl pyrophosphate of compound (1)
- and an aromatic compound selected from a compound of structural formula (III), (IV), (V), and (VI):
- wherein,
- R2 is —H or —OH
- R3 is —H or —COOH;
- and
- R4 is —H, —OH, linear or branched C1-C10 alkyl, linear or branched C1-C10 alkyl-amide, linear or branched C1-C10 alkyl-amine, linear or branched C1-C10 alkyl-alkylene, linear or branched C1-C10 alkyl-alkoxy, or C1-C10 alkyl-aryl, wherein any of the C1-C10 groups is optionally substituted with a —OH, —OCH3, or a halogen.
A method for preparing a cyclolavandulyl-substituted aromatic compound comprising:
- (a) contacting under suitable reaction conditions cyclolavandulyl diphosphate synthase (CLDS), dimethylallyl pyrophosphate, a prenyltransferase, and an aromatic compound selected from a compound of structural formulas (III), (IV), (V), and (VI)
- wherein,
- R2 is —H or —OH
- R3 is —H or —COOH;
- and
- R4 is —H, —OH, linear or branched C1-C10 alkyl, linear or branched C1-C10 alkyl-amide, linear or branched C1-C10 alkyl-amine, linear or branched C1-C10 alkyl-alkylene, linear or branched C1-C10 alkyl-alkoxy, or C1-C10 alkyl-aryl, wherein any of the C1-C10 groups is optionally substituted with a —OH, —OCH3, or a halogen;
- and
- (b) recovering the cyclolavandulyl-substituted aromatic compound from the reaction mixture.
A composition comprising a cyclolavandulyl diphosphate synthase (CLDS), dimethylallyl pyrophosphate, a prenyltransferase, and an aromatic compound selected from a compound of structural formulas (III), (IV), (V), and (VI)
- wherein,
- R2 is —H or —OH
- R3 is —H or —COOH;
- and
- R4 is —H, —OH, linear or branched C1-C10 alkyl, linear or branched C1-C10 alkyl-amide, linear or branched C1-C10 alkyl-amine, linear or branched C1-C10 alkyl-alkylene, linear or branched C1-C10 alkyl-alkoxy, or C1-C10 alkyl-aryl, wherein any of the C1-C10 groups is optionally substituted with a —OH, —OCH3, or a halogen.
Dependencies are inferred from the claim text.