Production of guaialene and cyperazulenone

文档序号:1301703 发布日期:2020-08-07 浏览:17次 中文

阅读说明:本技术 愈创木烯和莎草薁酮的生产 (Production of guaialene and cyperazulenone ) 是由 A·戈克 J·查培迪尔 B·希林格 F·施罗德 于 2018-11-21 设计创作,主要内容包括:提出了用于由α-愈创木烯生产莎草薁酮的方法,特别地通过氧化C(3)来进行,其中α-愈创木烯由前体通过倍半萜合酶生产。倍半萜合酶在微生物在产生。(A process for the production of cyperazulenone from α -guaiene is proposed, in particular by oxidation of C (3), wherein α -guaiene is produced from a precursor by a sesquiterpene synthase.)

1. A process for the production of cyperazulenone from α -guaialene, in particular by oxidation of the C (3) position, wherein the α -guaialene is produced from a precursor by a sesquiterpene synthase, wherein the sesquiterpene synthase is produced in a microorganism.

2. The method of claim 1, wherein the microorganism is cultured under conditions suitable for the production of α -guaiene.

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

4. The method of any one of claims 1-3, wherein the microorganism is a recombinant microorganism.

5. The method according to any one of claims 1 to 4, wherein the precursor is an acyclic precursor, in particular farnesyl pyrophosphate.

6. The method of any of claims 1-5 wherein the sesquiterpene synthase has at least 70%, preferably at least 80%, more preferably at least 90%, even more preferably at least 95% sequence identity with SEQ ID No. 2, SEQ ID No. 4 or SEQ ID No. 6.

7. The process of any of claims 1-6, wherein the cyperazulene ketone is produced from α -guaiene by oxidation selected from the group consisting of transition metal catalysis, organic catalysis, chromium oxidation, selenium oxidation, manganese oxidation, air oxidation, enzymatic oxidation, electrochemical oxidation, and combinations thereof.

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

9. The process of claim 8, wherein the cyperazulene ketone is produced from α -guaiene by ferriporphyrin catalysis comprising the steps of:

-forming a mixture comprising α -guaialene and an iron (III) -X porphyrin complex catalyst in a solvent;

-introducing molecular oxygen into the mixture;

-oxidation of the C (3) position of α -guaialene for the production of cyperazulenone.

10. The process of claim 7, wherein the cyperazulene ketone is produced from α -guaiene by an organocatalysis, in particular comprising the following steps:

-forming a mixture comprising α -guaiene, an organic catalyst, preferably selected from N-hydroxyphthalimide and tetrachloro-N-hydroxyphthalimide, and an oxidizing agent in a solvent;

-carrying out the oxidation of the C (3) position of α -guaialene.

Use of α -guaialene for the production of cyperazulenone, in particular by oxidation of the C (3) position, wherein the α -guaialene is produced from a precursor, in particular an acyclic precursor, by a sesquiterpene synthase wherein the sesquiterpene synthase is produced in a microorganism.

12. A flavor or fragrance ingredient obtainable by the process of any one of claims 1 to 11.

13. A flavour or fragrance ingredient, in particular an ingredient according to claim 12, wherein the cyperazulenone fraction comprises 10-95wt. -%, preferably 20-70wt. -%, even more preferably 25-50wt. -%.

14. A flavor or fragrance ingredient according to claim 13, additionally comprising ketone 5

15. Use of a flavour or fragrance ingredient according to any one of claims 12-14.

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