Process for the production of L-amino acids

Details Process for the production of L-amino acids Process for the production of L-amino acids

1988-09-23

1991-12-10

Elmore, Carolyn

Chemistry: molecular biology and microbiology

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

Preparing alpha or beta amino acid or substituted amino acid...

435106, 435107, 435108, 435110, 435114, 435115, 435116, 4352532, 435280, 435872, 435109, C12P 4100, C12P 1312, C12P 1306, C12P 1304

Patent

active

050717529

DESCRIPTION:

BRIEF SUMMARY
The invention relates to a process for the production of L-amino acids of general formula I ##STR3## in which R.sub.1 means an alkyl radical with at most 12 carbon atoms optionally substituted by hydroxy groups, mercapto groups, halogen atoms, amino groups, carbonyl groups or guanidino groups and/or interrupted by oxygen atoms, nitrogen atoms or sulfur atoms, and in the case of mercapto compounds of formula I also their dithio compounds, which is characterized in that the microorganism Nocardia spec. DSM 3306 or its enzymes are allowed to act on a D,L-imidazolidinedione derivative of general formula II ##STR4## in which R.sub.1 has the above-named meaning or, in the case of mercapto compounds of formula II, also on their dithio compounds.
The D,L-imidazolidinedione derivatives of general formula II and therefore also L-amino acids of general formula I produced from them can carry as substituents R.sub.1, for example, the methyl group, the ethyl group, the propyl group, the 1-methylethyl group, the butyl group, the 1-methylpropyl group, the 2-methylpropyl group, the 1,1-dimethylethyl group, the pentyl group, the 1-methylbutyl group, the 3-methylbutyl group or the hexyl group. Especially preferred alkyl groups R.sub.1 are those with at most 6 carbon atoms, such as the methyl group of the process product alanine, the 1-methylethyl group of valine, the 2-methylpropyl group of leucine, the 1-methylpropyl group of isoleucine or the ethyl group of the alpha-aminobutyric acid.
The alkyl groups R.sub.1 can optionally be substituted by hydroxy groups, mercapto groups, halogen atoms, amino groups, carbonyl groups or guanidino groups, and single substituted alkyl groups are preferred, or can be interrupted by oxygen atoms (preferably one), nitrogen atoms (preferably one or two) or sulfur atoms (preferably one). As alkyl groups, which are substituted by hydroxy groups or mercapto groups, there can be especially emphasized the hydroxymethyl group of serine, the 1-hydroxyethyl group of threonine, the mercaptomethyl group of cysteine, the 2-mercaptoethyl group of homocysteine and the 1-mercapto-1-methylethyl group of beta-thiovaline. As an alkyl group R.sub.1 interrupted by a sulfur atom there can be emphasized the 2-methyl thioethyl group of methionine. Alkyl groups R.sub.1, which carry an amino group or a guanidino group as substituents R.sub.1, are, for example, the 2-amino ethyl group of the alpha,gamma-diaminobutyric acid, 3-aminopropyl group of ornithine, the 3-guanidinopropyl group of arginine and the 4-aminobutyl group of lysine. Suitable as oxy-or oxoalkyl groups R.sub.1 are preferably those that also additionally are substituted by a hydroxy group, amino group or guanidino group and/or are interrupted by an oxygen atom or a nitrogen atom--more precisely an imino group; such groups are, for example, the acetoxymethyl group of 0-acetylserine, the 1-acetoxyethyl group of 0-acetylthaeonne, the carboxymethyl group of asparaginic acid, the 2-carboxyethyl group of glutaminic acid, the 2-methoxy-2-oxoethyl group of the omega-asparaginic acid monomethyl ester, the 3-guanidinooxy group of citruline or the 3-guanidino-3-oxopropyl group of canavanine.
The process according to the invention is performed by the use of the microorganism Nocardio spec. DSM 3306. This microorganism was isolated as earth samples, by it being mixed with a mineral salt medium, which contained 5-(2-methylpropyl)-hydantoin as sole nitrogen source, incubated and the grown culture are plated out on agar plates, which also contain 5-(2-methylpropyl)-hydantoin as sole nitrogen source.
The microorganism obtained was deposited at the German Collection of microorganisms (Deutsche Sammlung von Mikroorganismen, Grisebachstr. 8, D-3400 Goettingen) on May 9, 1985, and received the number DSM 3306 there. It is irrevocably available to experts.
Taxonomically, it has the following properties:


______________________________________ Colony morphology round, irregular edge, not translucent Cell morphology in young cultures bacilli 1.2 micrometers thick, 8

REFERENCES:
patent: 4094741 (1978-06-01), Yamada et al.
patent: 4211840 (1980-07-01), Nakamori et al.
patent: 4237227 (1980-12-01), Yamada et al.
patent: 4242452 (1980-12-01), Yamada et al.
CA 93:43950x (1980).
CA 107:5729g (1987).

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