Synthetic enzymes for the production of coniferyl alcohol,...

Details Synthetic enzymes for the production of coniferyl alcohol,... Synthetic enzymes for the production of coniferyl alcohol,...

1997-11-21

2003-02-25

Prouty, Rebecca E. (Department: 1652)

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing oxygen-containing organic compound

C435S189000, C435S025000, C435S325000, C435S320100, C435S069100, C435S252300, C536S023100, C536S023200

Reexamination Certificate

active

06524831

ABSTRACT:

The present invention relates to synthesis enzymes for the production of coniferyl alcohol, coniferylaldehyde, ferulic acid, vanillin and vanillic acid, the use thereof for the production of coniferyl alcohol, coniferylaldehyde, ferulic acid, vanillin and vanillic acid, DNA coding for the aforementioned enzymes and microorganisms transformed therewith.
The first article relating to the degradation of eugenol was written by Tadasa in 1977 (Degradation of eugenol by a microorganism. Agric. Biol. Chem. 41, 925-929). It describes the degradation of eugenol with a soil isolate which was presumed to be Corynebacterium sp. In this process ferulic acid and vanillin were identified as intermediate degradation products and the subsequent degradation was assumed to proceed via vanillic acid and protocatechuic acid.
In 1983 another article by Tadasa and Kyahara appeared (Initial Steps of Eugenol Degradation Pathway of a Microorganism. Agric. Biol. Chem. 47, 2639-2640) on the initial steps of eugenol degradation, this time with a soil isolate which was identified to be Pseudomonas sp. In this article eugenol oxide, coniferyl alcohol and coniferylaldehyde were described as intermediates for the formation of ferulic acid.
Also in 1983 a report by Sutherland et al. appeared (Metabolism of cinnamic, p-coumaric, and ferulic acids by
Streptomyces setonii
. Can. J. Microbiol. 29, 1253-1257) on the metabolism of cinnamic, p-coumaric and ferulic acids by
Streptomyces setonii
. In this process ferulic acid was degraded via vanillin, vanillic acid and protocatechuic acid, the ring-cleaving enzymes catechol 1,2-dioxygenase and protocatechuate 3,4-dioxygenase having been indirectly identified in the cell-free extract.
In 1985 Ötük (Degradation of Ferulic Acid by
Escherichia coli
. J. Ferment. Technol. 63, 501-506) reported on the degradation of ferulic acid by a strain of
Escherichia coli
isolated from decaying bark. Here as well vanillin, vanillic acid and protocatechuic acid were found as degradation products.
In 1987 a German patent application by BASF appeared [“Verfahren zur Gewinnung von Coniferylaldehyd und Mikroorganismus dafur” (A process for obtaining coniferylaldehyde and a microorganism therefor); DE-A 3 606 398] for a process for producing coniferylaldehyde from eugenol using a mutant of
Arthrobacter globiformis
. The aim was to obtain natural vanillin.
Abraham et al. (Microbial transformations of some terpenoids and natural compounds: Bioflavour '87, pp. 399-413) reported at “Bioflavor '87” on the metabolisation of eugenol by various microorganisms. When fungi were used, dimers were predominantly found and only when isoeugenol was used
Aspergillus niger
ATCC 9142 did also form vanillin.
In 1988 Omori et al. described a process (Protocatechuic acid production from trans-ferulic acid by Pseudomonas sp. HF-1 mutants defective in protocatechuic acid catabolism. Appl. Microbiol. Biotechnol. 29, 497-500) for obtaining protocatechuic acid with a mutant of a Pseudomonas sp. HF-1. The only intermediate mentioned was vanillic acid.
In 1989 the metabolism of ferulic acid by two fungi,
Paecilomyces variotii
and
Pestalotia palmarum
was described by Rahouti et al. (Metabolism of ferulic acid by
Paecilomyces variotii
and
Pestalotia palmarum
. Appl. Environ. Microbiol. 55, 2391-2398). It was postulated that degradation to form vanillic acid proceeded via 4-vinylguaiacol and vanillin.
In 1990 two Japanese patent applications by Hasegawa appeared on a new Pseudomonas sp. and a dioxygenase enzyme (Novel Pseudomonas sp. and dioxygenase enzyme. JP 2195-871:25.10.88-JP-267 284 (2.8.90) 9.3.89 as 055111) and on a new method for the production of an aldehyde such as for example vanillin (A new method for the preparation of aldehyde e.g. vanillin. JP 2200-192:25.10.88-JP-267 285 (8.8.90) 9.3.89 as 055112). The method is however not based on eugenol but on various starting compounds such as isoeugenol and coniferyl alcohol. Nor is there any identity between the dioxygenase claimed in the aforementioned patent applications and the enzymes claimed in the present application.
Bacteria of the genera Serratia, Enterobacter or Klebsiella were used in EP-A 405 197 (Production of natural vanillin by microbial oxidation of eugenol or isoeugenol) for the microbial oxidation of eugenol and isoeugenol. However, only when isoeugenol was used the process did produce high conversion rates; the results were very poor using eugenol.
In 1991 EP-A 453 368 appeared [“Production de vanilline par bioconversion de précurseurs benzeniques” (Production of vanillin by the bioconversion of benzene precursors)], in which the reaction to form vanillin from vanillic acid and ferulic acid using a basidiomycete—
Pycnoporus cinnabarinus
CNCM I-937 and I-938—was observed.
In 1992 the Takasago Perfumery Company was granted a Japanese patent (Preparation of vanillin, coniferyl-alcohol and -aldehyde, ferulic acid and vanillyl alcohol—by culturing mutant belonging to Pseudomonas genus in presence of eugenol which is oxidatively decomposed; JP 05 227 980 21.1.1992) for the preparation of vanillin, coniferyl alcohol, coniferylaldehyde, ferulic acid and vanillyl alcohol from eugenol using a Pseudomonas mutant.
Also in 1992 U.S. Pat. No. 5,128,253 by Labuda et al. (Kraft General Foods) (Bioconversion process for the production of vanillin) was granted, in which a biotransformation process for the production of vanillin was described. Here as well the starting material was ferulic acid and the organisms used were
Aspergillus niger, Rhodotorula glutinis
and
Corvnebacterium glutamicum
. The crucial feature was the use of sulphydryl components (e.g. dithiothreitol) in the medium. In 1993 the subject matter of the patent also appeared in the form of a publication (Microbial bioconversion process for the production of vanillin; Prog. Flavour Precursor Stud. Proc. Int. Conf. 1992, 477-482).
EP-A 542 348 (Process for the preparation of phenylaldehydes) describes a process for the preparation of phenylaldehydes in the presence of the enzyme lipoxygenase. Eugenol and isoeugenol are for example used as substrates. We have attempted to rework the process using eugenol, but have not succeeded in confirming the results of the reactions.
DE-A 4 227 076 [Verfahren zur Herstellung substitutierter Methoxyphenole und dafür geeigneter Mikroorganismus (Process for the production of substituted methoxyphenols and a microorganism suitable for said process)] describes the production of substituted methoxyphenols with a new Pseudomonas sp. The starting material used is eugenol and the products are ferulic acid, vanillic acid, coniferyl alcohol and coniferylaldehyde.
Also in 1995 a comprehensive review by Rosazza et al. (Biocatalytic transformation of ferulic acid: an abundant aromatic natural product; J. Ind. Microbiol. 15, 457-471) appeared on possible methods of biotransformation using ferulic acid.


REFERENCES:
patent: 4847422 (1989-07-01), Klemola et al.
patent: 5017388 (1991-05-01), Rabenhorst et al.
patent: 5128253 (1992-07-01), Labuda et al.
patent: 5358861 (1994-10-01), Markus et al.
patent: 5510252 (1996-04-01), Hopp et al.
patent: 5712132 (1998-01-01), Mane et al.
patent: 0 583 687 (1984-02-01), None
patent: 0 761 817 (1997-03-01), None
patent: WO 94/02621 (1994-02-01), None
patent: WO 95/02062 (1995-01-01), None
patent: WO 97/35999 (1997-10-01), None
Fraaije, M. et al., Eur. J. Biochem., vol. 234, pp. 271-277, 1995.*
Lee, C. et al., Science, vol. 239, pp. 1288-1291, 1988.*
Studier, F. et al., Meth. Enzymol., vol. 185, pp. 60-89, 1990.*
Matthews, C. et al., Biochemistry, The Benjamin/Cummings Publishing Co., Inc., Redwood City, CA, Chapter 1, p. 13, 1990.*
Tadasa, Agric.Biol.Chem., 41 (6), 925-929 (1977): “Degradation of Eugenol by a Microorganism”.
Tadasa et al., Agric.Biol.Chem., 47 (11), 2639-2640 (1983): “Initial Steps of Eugenol Degradation Pathway of a Microorganism”.
Sutherland et al., Can.J.of Microbiology, 29, 1253-1257 (1983): “Metabolism of cinnamic, p-coumaric, , and ferulic acids byStreptomyces se

Affiliated with

Also associated with

Rating

Synthetic enzymes for the production of coniferyl alcohol,... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthetic enzymes for the production of coniferyl alcohol,..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthetic enzymes for the production of coniferyl alcohol,... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3157729