Process for the preparation of L-amino acids and amino acid amid

Details Process for the preparation of L-amino acids and amino acid amid Process for the preparation of L-amino acids and amino acid amid

1990-01-05

1992-03-31

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

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

Process involving micro-organisms of different genera in the...

435106, 435108, 435110, 435113, 435114, 435115, 435250, C12P 1302, C12P 1304, C12P 3900, C12P 4100

Patent

active

051007827

DESCRIPTION:

BRIEF SUMMARY
The invention relates to the process for the preparation of L-amino acids and amino acid amides as characterized in the claims.
Processes for the fermetative production of L-amino acids from D,L-.alpha.-aminonitriles are conventional (European Patent Application 23214). In these previously known methods, the L-form of the .alpha.-aminonitrile is hydrolyzed to the L-amino acid whereas the o D-form of the .alpha.-aminonitrile either is not hydrolyzed at all or is hydrolyzed merely to the D-amino acid amide. As a consequence thereof, the conventional methods theoretically allow only yields of 50%.
It has now been found hat certain micro-organisms not only possess L-amino acid amide amidases but moreover also contain amino acid amide racemases which racemize the D-amino acid amides to D,L-.alpha.-amino acid amides. These microorganisms thus have the capability to convert also the D-form of the D,L-.alpha.-amino acid amides into L-amino acids. Finding such micro-organisms does not present any difficulties to one skilled in the art. Various microorganisms are tested by means of the usual screening methods whether they show the capability of converting D-amino acid amides into L-amino acids. Previously known micro-organisms possessing this capability to an excellent degree are, in accordance with investigations conducted in-house, Arthrobacter sp. ATCC 31 652 and Corynebacterium sp. ATCC 31 662.
It has furthermore been found that micro-organisms exist having the capability of converting .alpha.-aminonitriles into amino acid amides without hydrolyzing them further. A microorganism has been isolated from soil samples which has the capability of splitting D,L-.alpha.-amino-.beta.-phenylpropionitrile to phenylalanine.
This microorganism has the following taxonomic properties:


______________________________________ Colony morphology round, smooth-edged, translucent, slimy Cytomorphology immobile, short rods length 1.5-2.5 .mu.m, width 1 .mu.m Gram stain Gram-negative Endospores negative Catalase positive Cytochrome-C oxidases negative Citrate use positive Nitrite from nitrate negative Voges-Proskauer negative Methyl red negative Indole formation negative Urease positive H.sub.2 S formation negative Use of sugar acid from glucose, no acid from sucrose, fructose, lactose, maltose, mannitol, glycerol, no gas formation ______________________________________
Based on its morphological and physiological properties, the microorganism was identified as Actinetobacter calcoaceticus in accordance with the criteria of "Bergey's Manual of Determinative Bacteriology".
This microorganism was mutated by means of N-methyl-N'-nitro-N-nitrosoguanidine (MNNG), and an amidase-free mutant was isolated having the capability of hydrolyzing D,L-.alpha.-aminonitriles only as far as to the stage of the D,L-.alpha.-amino acid amides. This mutant was deposited on Oct. 17, 1986 in the "Deutsche Samlung von Mikro-organismen" [German Culture Collection], Grisebachstrasse 8, Gottlingen, Germany, under the number DSM 3875.
With the aid of the novel microorganism Actinetobacter calcoaceticus SM 3875, as well as the previously known microorganisms Arthrobacter sp. ATCC 31 652 or Corynebacterium sp. ATCC 31 662, it is now possible to hydrolyze D,L-.alpha.-aminonitriles to L-amino acids without D-amino acid amides remaining as by-products.
Amino acids that can be synthetized by means of the process of this invention are, for example, the amino acids listed in Hoppe-Seyler's "Z. Physiol. Chem." 348:256-261 (1967), as well as their derivatives wherein optionally hydroxy groups, thiol groups, amino groups and carboxy groups present in the residue A according to Formula I are blocked by suitable blocking groups.
With respect to their industrial exploitation, those amino acids are preferred process products of the synthesis according to the invention wherein the residues A have the meanings set forth in claim 4.
Suitable alkyl residues A are those carrying, for example, the methyl group, the ethyl group, t

REFERENCES:
patent: 4080259 (1978-03-01), Boesten et al.
patent: 4276380 (1981-06-01), Yukawa et al.
patent: 4366250 (1982-12-01), Jallageas et al.
patent: 4427774 (1984-01-01), Yukawa et al.
patent: 4705752 (1987-11-01), Boesten et al.
patent: 4812403 (1989-03-01), Boesten et al.
patent: 4847412 (1989-07-01), Boesten et al.
patent: 4880737 (1989-11-01), Kerkhoffs et al.
patent: 4918196 (1990-04-01), Doya et al.
Derwent Abs. 86-346609/52, Godtfredse et al, WO8607386 (Dec. 1986).
Derwent Abs. 90-227356/30, J02154692, Ashai Chem. 6-1990.
Derwent Abs. 87-025758/07 J61282087, Asahi Chem. 12-86.

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