Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound
Patent
1982-12-01
1985-12-24
Wiseman, Thomas G.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing oxygen-containing organic compound
435132, 435134, 435136, 435148, 435155, 435195, 435198, 435280, C12P 726, C12P 702, C12P 700, C12P 764, C12P 742, C12N 914, C12N 120, C07B 1902
Patent
active
045606560
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention is concerned with a microbial process for the production of optically active .gamma.-decalactone. Considerable time and effort have been expended by microbiologists in the search for better processes for the production of optically active lactones. U.S. Pat. No. 3,076,750 disclose a method of preparing certain optically active lactones and the corresponding hydroxycarboxylic acids by microbial reduction of ketocarboxylic acids. The metabolism of ricinoleic acid by some Candida strains was investigated by Okui et al. (J. Biochemistry, 54,536-540, 1963) who showed that .gamma.- hydroxydecanoic acid was an intermediate in the oxidative degradation of ricinoleic acid. However, only trace amounts of .gamma.-hydroxydecanoic acid were recovered from the fermentation medium due to the metabolysis of .gamma.-hydroxydecanoic acid upon completion of the fermentation, and the toxicity of ricinoleic acid to the microorganism, which limits the amount of substrate that can be used.
SUMMARY OF THE INVENTION
This invention provides a method of producing optically active .gamma.-hydroxydecanoic acid which coprises culturing or incubating a microorganism capable of hydrolyzing castor oil, and effecting .beta.-oxidation of the resulting hydrolysate in the presence of castor oil, to produce .gamma.-hydroxydecanoic acid.
In another embodiment, the invention provides a method of producing optically active .gamma.-hydroxydecanoic acid which comprises enzymatically hydrolyzing castor oil using lipase to form an enzymatic hydrolysate and culturing or incubating a microorganism capable of effecting .beta.-oxidation of the enzymatic hydrolysate in the presence of said hydrolysate to produce .gamma.-hydroxydecanoic acid.
In still another embodiment, the invention provides a method of producing optically active .gamma.-hydroxydecanoic acid which comprises culturing or incubating a microorganism capable of hydrolyzing castor oil and a microorganism capable of effecting .beta.-oxidation of castor oil hydrolysate in the presence of castor oil to produce .gamma.-hydroxydecanoic acid.
DETAILED DESCRIPTION OF THE INVENTION
The invention provides a fermentation process for the production of optically active .gamma.-hydroxydecanoic acid which may optionally be converted by lactonization to .gamma.-decalactone. Depending on the embodiment of the invention employed, the fermentation process involves culturing or incubating a microorganism capable of hydrolyzing castor oil and effecting .beta.-oxidation of the resulting hydrolysate, or a microorganism capable of effecting .beta.-oxidation of hydrolysate of castor oil, or a microorganism capable of effecting .beta.-oxidation of an enzymatic hydrolysate of castor oil, in a suitable medium in the presence of the castor oil or castor oil hydrolysate substrate. The use of castor oil or castor oil hydrolysate as the substrate is determined by the microorganism(s) employed in the process. A co-oxidant may be added to the culture medium in order to increase the yield of the process.
The selection of the appropriate microorganism for the process is crucial depending on the embodiment of the invention employed, the yield of product required, and the resistance to the toxicity of the fatty acids found in the castor oil hydrolysate. The microorganisms in the invention may be bacteria, yeast or filamentous fungi. Where a microorganism is employed to hydrolyze the castor oil substrate and .beta.-oxidize the resulting hydrolysate, the preferred microorganisms are: Aspergillus oryzae, Candida rugosa, Geotrichum klebahnii or Yarrowia lipolytica, (formerly known as Saccharomycopsis lipolytica and previously Candida lipolytica), more preferably Yarrowia lipolytica. Where the microorganism is employed to only .beta.-oxidize castor oil hydrolysate, the preferred microorganisms are: Hansenula saturnus, Candida guilliermondii, Candida albicans, Candida krusei, Candida parakrusei, Candida pseudotropicals, Candida stellatoidea, Candida tropicalis, Aspergillus oryzae, Cand
REFERENCES:
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patent: 4275081 (1981-06-01), Coleman et al.
patent: 4302540 (1981-11-01), Hirata et al.
Okui, S. et al., The Journal of Biochemistry, vol. 54, No. 6, pp. 536-540, (1963), "Metabolism of Hydroxy Fatty Acids".
Final, I. L. Organic Chemistry, vol. 1, 6th Edition, Longman Group Limited, London, pp. 468-472, (1973).
Okui et al., Biochim. Biophys. Acta, 70, (1963), pp. 346-348.
Farbood Mohamad I.
Willis Brian J.
Fritzsche Dodge & Olcott Inc.
Teskin Robin
Wiseman Thomas G.
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