Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing heterocyclic carbon compound having only o – n – s,...
Patent
1995-12-28
1998-05-19
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing heterocyclic carbon compound having only o, n, s,...
435118, 435119, 435120, 435121, 435122, 435123, 435124, 435125, 435126, 435128, 435156, 4352521, 435855, 549369, 549374, C07C 5960, C12P 722, C12P 724, C12N 120
Patent
active
057534713
DESCRIPTION:
BRIEF SUMMARY
The invention relates to a process for the biotechnological preparation of alcohols, aldehydes and carboxylic acids.
Highly functionalized alcohols, aldehydes and carboxylic acids are interesting products which are in demand for preparing drugs, polymers, fine chemicals etc. and which are often synthesized by oxidation of appropriate precursors.
As a rule, chemical oxidations show low regiospecificities. In addition, the reagents required for the oxidation are often toxic and/or difficult to handle.
It is known that bacteria are able in principle to oxidize methyl groups.
Thus, Raymond et al. (Appl. Microbiol. 15, (1967) 857-865) describe the oxidation of methyl groups by cooxidation with n-paraffins in the genus Nocardia.
It is known that the genus Pseudomonas oxidizes p-cymene in three steps via the alcohol and aldehyde to p-isopropylbenzoic acid (J. Bacteriol. 129, (1977) 1356-1364 and 1365-1374 and ibid 171, (1989) 5155-5161).
Besides this oxidation of benzylic methyl groups, a number of microorganisms is known to oxidize allylic methyl groups.
Thus, Noma et al. describe the oxidation of limonene by Aspergillus cellulosae (Phytochemistry, 31, (1992) 2725-2727) inter alia to perillyl alcohol.
Pseudomonas incognita oxidizes linalool inter alia to 8-hydroxylinalool (J. Bacteriol. 171, (1989) 5155-5161).
Bhattacharyya et al. have investigated in a series of studies (Indian. J. Biochem. 5, (1968) 79-91 and 92-101, Indian. J. Biochem. 3, (1966) 144-157 and Biochem. Biophys. Res. Commun. 29, No. 3, (1967) 275-279) the oxidation of terpenes (eg. limonene, .alpha.- and .beta.-pinene) by Pseudomonas PL strains. These PL strains also oxidize p-cymene to cumic acid (Indian. J. Biochem. 5, (1968) 161-167). However, the cited studies show that, besides the required methyl group oxidations in benzylic and allylic positions, the microorganisms bring about a number of additional oxidations on the precursors used (such as limonene, p-cymene etc.).
The oxidation described in CH-B 677 791 and Tetrahedron 48, (1992) 6681-6688 of an allylic methyl group of terpenes using microorganisms of the genera Bacillus, Pseudomonas, Absidia, Rhizopus, Streptomyces, Mycobacterium, Cunninghamella, Nocardia etc. is likewise associated with the problem of side reactions.
The described reactions therefore cannot be applied industrially.
EP-A 442 430, EP-A 466 042 and EP-A 477 828 describe industrially utilizable methyl group oxidations. The disadvantage of these reactions is, however, the induction of the microorganisms by, for example, p-xylene as sole source of carbon and energy. In addition, the described reactions are restricted to 5- and 6-membered heterocycles.
Industrial processes using microorganisms which selectively oxidize both benzylic and allylic methyl group positions in a wide range of aromatic, heteroaromatic and aliphatic substances have not hitherto been disclosed.
We have now found an industrially utilizable process for the microbial preparation of alcohols, aldehydes and carboxylic acids.
The invention relates to a process for preparing compounds of the formula I ##STR1## where R.sup.1 is hydrogen, C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl or unsubstituted or substituted aryl, or substituted aryl, or bonded, a) a 6-membered ring which may contain 1 or 2 other double bonds and/or be substituted by 1, 2 or 3 halogen atoms, C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, C.sub.1-4 -acyl, C.sub.1-4 -alkoxy groups and/or 1 or 2 cyano, amino, C.sub.1-4 -alkylamino or di-C.sub.1-4 -alkylamino groups and/or one nitro group, and/or may be fused to another aromatic or heteroaromatic 6-membered ring to give a ring system which may be substituted by one to four C.sub.1-4 -alkoxy, C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, cyano, nitro, carboxyl, C.sub.1-4 -alkoxycarbonyl, amino, C.sub.1-4 -alkylamino, di-C.sub.1-4 -alkylamino and/or unsubstituted or substituted benzoyl group and/or one to four halogen atoms, or b) a heterocyclic 5-membered ring which contains 1, 2 or 3 heteroatoms and/or may contain another double bond and may be fused to another arom
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patent: 5213973 (1993-05-01), Hoeks
patent: 5217884 (1993-06-01), Zimmermann et al.
patent: 5236832 (1993-08-01), Kiener
Hook G. et al., Biochem. J., vol. 102, No. 2, Feb. 1967, pp. 504-510.
Ballal et al., Biochem. and Biophys. Res. Comm., vol. 29, No. 3, 1967, pp. 275-280.
Raymond et al., Appl. Microbio., vol. 15, No. 4, Jul. 1967, pp. 857-865.
Madhyastha et al., Ind. J. Biochem., vol. 5, pp. 161-167, 1968.
Dhavalikar et al., Ind. J. Biochem., vol. 3, pp. 144-157, 1966.
Shukla et al., Ind. J. Biochem., vol. 5, pp. 79-91, 92-101, 1968.
Noma et al., Phytochem., vol. 31, No. 8, pp. 2725-2727, 1992.
De Smet et al., J. of Bacteriology, vol. 171, No. 9, Sep. 1989, pp. 5155-5161, 1989.
De Frank et al., J. of Bacteriology, vol. 129, No. 3, Mar. 1977, pp.. 1356-1364, pp. 1365-1374.
Abraham et al., Tetrahedron, vol. 48, No. 32, pp. 6681-6688, 1992.
Balkenhohl Friedhelm
Hauer Bernhard
Ladner Wolfgang
Pressler Uwe
Schnell Ursula
BASF - Aktiengesellschaft
Lilling Herbert J.
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