Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing compound containing saccharide radical
Patent
1997-09-25
1999-01-19
Lilling, Herbert J.
Chemistry: molecular biology and microbiology
Micro-organism, tissue cell culture or enzyme using process...
Preparing compound containing saccharide radical
435147, 435189, 568426, 568431, 568432, 568436, 568437, 568438, C12P 724, C12P 1944, C07C 4758, C07H 15203
Patent
active
058612866
DESCRIPTION:
BRIEF SUMMARY
The invention relates to a biochemical process for the preparation of certain aromatic substances.
The term aromatic substances means natural aldehydes having an aromatic interest, that is, a perfume and/or a flavour suitable for the use thereof in the food, pharmaceutical or perfume industries.
Various processes for the preparation of natural aldehydes have already been described. For example: benzaldehyde and acetaldehyde by means of a "retro-aldol" reaction, application no. 542 348, 368 describe processes for the preparation of vanillin involving the use of microorganisms, compositions of vanilla by means of vegetable cells.
Said processes require, however, the use of specific and expensive compounds or products which have to be used under relatively stringent conditions.
The object of the present invention is to overcome the disadvantages of the art and allows the preparation of aromatic substances by means of compounds which are easy to procure, inexpensive and under reaction conditions which are simple to achieve.
To its credit, the applicant has, in fact, established that it was possible to prepare aromatic substances having the formula: ##STR2## by submitting to oxidation in the presence of at least one protein and at least one metal ion, a substrate corresponding to the formula ##STR3## wherein R.sub.1 may be a radical --H, --CH.sub.3, --CH.sub.2 OH, --CHO, --COOH, --OCH.sub.3, or --COO--CH(COOH)--CH.sub.2 --C.sub.6 H.sub.3 (OH).sub.2,
With regard to the radical R.sub.3, the glucoside of the radical 0-glucoside is chosen from the group comprising the glucopyranoside alone or attached to an oside such as glucopyranoside, rhamnopyranoside, arabinopyranoside.
Advantageously, the aromatic substances according to the invention belong to the group comprising vanillin, benzaldehyde, anisaldehyde and protocatechualdehyde.
The protein used in the process according to the invention may be chosen from: haemoglobin, cytochromes (c, P450 . . . ) and numerous oxydoreductases such as peroxydase, catalase, cytochrome oxydase, or dehydrogenases such as alcohol dehydrogenase, or oxygenases, ferredoxin and certain dioxygenases, context of the present invention, must be completed by a metal ion not contained in their structure, this metal ion being either in the free form or in the complexed form (for example, complexed with porphyrins or protoporphyrins); these may include gelatin, casein, bovine serum albumin.
Whatever the protein used in the process according to the invention, the metal ion in the free or complexed form is chosen from the group comprising iron, cobalt, copper, magnesium, manganese, and zinc.
Advantageously, several proteins and several metal ions in the free or complexed form, may be used simultaneously in the process according to the invention. Indeed, it was observed that the yields obtained were all the higher if they resulted from the use of the combination of at least two of the following compounds: a "simple" protein, a metalloprotein, a metal ion, a protoporphyrin, a porphyrin.
The process according to the invention has, in particular, the advantage that it may be used with compounds that are inexpensive and easy to procure. Moreover, the reaction conditions do not require any particular precautions as regards sterility or regulation of the reaction medium.
According to an advantageous embodiment of the process according to the invention, the metal ion in whatever form it may take is used in a quantity of 0.0005 to 0.2% by weight with respect to the substrate.
Advantageously, the substrates subjected to the joint action of a protein and a metal ion are chosen from the group comprising isoeugenol, eugenol, cinnamaldehyde, anethole and rosmarinic acid.
The proteins used in the process according to the invention may be used in the purified or unpurified form. In an unpurified form, said proteins may be used by way of compositions containing them such as a suspension of microbial cells, a ground preparation of cells, tissues or organs of vegetable or animal origin, or of a protein preconcentrat
REFERENCES:
Derwent Abstract 93-316614/40 JP05227980 (Sept. 07, 1993) Takasago Peerfumery Co. Ltd. Sep. 7, 1993.
Mane Jean
Zucca Joseph
Lilling Herbert J.
V. Mane Fils
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