Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Patent
1980-09-24
1982-12-28
Warden, Robert J.
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Resolution of optical isomers or purification of organic...
C07B 1902
Patent
active
043662501
DESCRIPTION:
BRIEF SUMMARY
The present invention concerns itself with a preparation process of optically active .alpha.-aminated acids by biological hydrolysis of corresponding .alpha.-amino amides or of corresponding .alpha.-amino nitriles.
Formerly the optically active .alpha.-aminated acids were prepared from racemic amino acids by resolution of stereoisomeres by the already known method, in particular by the formation of salts with other optically active compounds or by the resorting to resins, which offer certain stereospecific characteristics.
In addition to the fact, that these technical procedures are very delicate to be put into operation, they naturally impose an additional step at the time of the synthesis of amino acids from other products like the corresponding amino amides or the corresponding amino nitriles, which, generally, are the normal precursors of these amino acids.
Now, the present invention proposes a process, which will permit the direct preparation of the amino acid in optically active form, either from amino amides, or from amino nitriles.
For this purpose, the present invention concerns itself with a process of preparation of L.alpha.-amino acids, characterized by the fact, that the corresponding racemic .alpha.-amino amide is hydrolized in a liquid medium by an agent, which contains a L stereospecific amidase, and further, that the L.alpha.-amino acid, obtained from the non-hydrolized D.alpha.-amino amide, is then separated.
In a preferable method of operation pursuant to this invention the racemic L.alpha.-amino amide is prepared in situ from the corresponding L.alpha.-amino nitrile by action of an agent, which contains a general nitrilase.
In the following statements the terms "amino amide" or "amino nitrile" or "amino acid" comprise also the compounds in free form or in the form of salt, particularly of hydrochloride.
The agents, which are used in the framework of this invention, are preferably bacteria or non-cellular preparations of bacterial origin, which do not possess general amidase.
In the event, that the .alpha.-amino acid is prepared from the corresponding .alpha.-amino nitrile, it is especially interesting to note, that the bacterium or the a(non)-cellular preparation of bacterial origin possess both the L stereospecific amidase and the general nitrilase in such a manner, that only one source (mother liquid) or a(non)-cellular preparation of bacterial origin has to be used.
Of course, it is possible, by proceeding with nitrile, to effect the reaction in two steps, using two agents, which separately possess, the one the L stereospecific amidase, the other the general nitrilase.
The bacteria or the a(non)-cellular preparations of bacterial origin, come preferably from a mutant of a strain, which itself possesses a general amidase, which mutant is able to grow in a nutrient medium, containing monofluor acetamide through the loss of the general amidase.
Actually, it has been found, that in the event that strains which possess a general amidase, are made to grow in a nutrient medium containing monofluor-acetamide, they transform the monofluor-acetamide into monofluor acetic acid according to the reaction: make spontaneous defective mutants appear, which means, they no longer possess the general amidase, but only the L stereospecific amidase.
The mutants thus obtained are spontaneous mutants, but, of course, it is possible to utilize the known mutagene agents, like ultraviolet radiation, X or .gamma. or the chemical compounds like ethylmethane sulfonate, nitrous acid, alkylating agents, nitroso-guanidine, or acryflavine, for example, in order to increase the frequency of appearance of strains, which possess the L stereospecific amide base.
Among the strains, which possess a general amidase, one has to cite particularly the genus Bacillus, Bacteridium as defined by Prevot, Micrococcus and Brevibacterium as defined by Bergey. As regards the more preferred, these bacteria are chosen among the strains of the collection of the Professorship for Genetics and Microbiology of the National Superior Agronom
REFERENCES:
patent: 2511867 (1950-06-01), Neuberg et al.
patent: 3635795 (1972-01-01), Demain et al.
patent: 3971700 (1976-07-01), Boester
patent: 4080259 (1978-03-01), Boester et al.
Chemical Abstracts, vol. 89, No. 19, 161521y; 19786.
Arnaud Alain
Galzy Pierre
Jallageas Jean C.
ANVAR
Warden Robert J.
LandOfFree
Preparation process of optically active .alpha.-aminated acids b does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation process of optically active .alpha.-aminated acids b, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation process of optically active .alpha.-aminated acids b will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1337667