Production of guaiene and rotundone

Patent metadata

Field	Value
Publication number	US-11485985-B2
Application number	US-201816765649-A
Country	US
Kind code	B2
Filing date	Nov 21, 2018
Priority date	Dec 5, 2017
Publication date	Nov 1, 2022
Grant date	Nov 1, 2022

Abstract

A process for producing rotundone from α-guaiene, in particular by oxidation of the C(3) position, wherein the α-guaiene is produced from a precursor by a sesquiterpene synthase. The sesquiterpene synthase is produced in a microorganism.

First claim

The invention claimed is:

1. A process for producing rotundone from α-guaiene, wherein the α-guaiene is produced from a precursor by a sesquiterpene synthase, wherein the sesquiterpene synthase is produced in a microorganism, and wherein the sesquiterpene synthase has a sequence identity with SEQ ID NO.: 2, SEQ ID NO.: 4 or SEQ ID NO.: 6 of at least 70%.

2. The process according to claim 1 , wherein the microorganism is cultured under conditions suitable to produce α-guaiene.

3. The process according to claim 1 , wherein the sesquiterpene synthase is isolated from the microorganism prior to production of α-guaiene.

4. The process according to claim 1 , wherein the microorganism is a recombinant microorganism.

5. The process according to claim 1 , wherein the precursor is an acyclic precursor.

6. The process according to claim 1 , wherein rotundone is produced from α-guaiene by an oxidation selected from the group consisting of transition metal catalysis, organocatalysis, chromium oxidation, selenium oxidation, manganese oxidation, aerial oxidation, enzymatic oxidation, electrochemical oxidation and combinations thereof.

7. The process according to claim 6 , wherein rotundone is produced from α-guaiene by transition metal catalysis and the transition metal is selected from the group consisting of iron, copper, vanadium, manganese, molybdenum, cobalt, ruthenium, palladium, iridium, rhodium, titanium, chromium, gold, osmium and combinations thereof.

8. The process according to claim 7 , wherein rotundone is produced from α-guaiene by iron porphyrin catalysis comprising the steps of:
Forming a mixture containing α-guaiene and an iron (III)-X porphyrin complex catalyst in a solvent;
Introducing molecular oxygen into the mixture;
Effecting production of rotundone oxidation of the C(3) position of α-guaiene.

9. The process according to claim 6 , wherein rotundone is produced from α-guaiene by organocatalysis.

10. The process according to claim 1 , wherein rotundone is produced from α-guaiene by oxidation of the C(3) position.

11. The process according to claim 5 , wherein the precursor is farnesyl pyrophosphate.

12. The process according to claim 1 , wherein the sesquiterpene synthase has a sequence identity with SEQ ID NO.: 2, SEQ ID NO.: 4 or SEQ ID NO.: 6 of at least 80%.

13. The process according to claim 12 , wherein the sesquiterpene synthase has a sequence identity with SEQ ID NO.: 2, SEQ ID NO.: 4 or SEQ ID NO.: 6 of at least 90%.

14. The process according to claim 13 , wherein the sesquiterpene synthase has a sequence identity with SEQ ID NO.: 2, SEQ ID NO.: 4 or SEQ ID NO.: 6 of at least 95%.

15. The process according to claim 9 , wherein rotundone is produced from α-guaiene by organocatalysis comprising the steps of:
Forming a mixture containing α-guaiene, an organocatalyst, selected from the group consisting of N-hydroxyphthalimide and tetrachloro-N-hydroxyphthalimide, and an oxidant in a solvent; and
Effecting oxidation of the C(3) position of α-guaiene.

Assignees

• Givaudan Sa

Inventors

• Goeke Andreas
• Charpentier Julie
• Schilling Boris
• Schröder Fridtjof

Classifications

• C07C49/637

  the condensed ring system containing ten carbon atoms · CPC title

• C12P7/38 Primary

  Cyclopentanone- or cyclopentadione-containing products · CPC title

• A23L29/03

  Organic compounds · CPC title

• C12P5/002

  cyclic (compounds containing at least three condensed carbocyclic rings C12P15/00) · CPC title

• C11B9/0049

  the condensed rings sharing two common C atoms · CPC title