Chemistry: molecular biology and microbiology – Process of utilizing an enzyme or micro-organism to destroy... – Resolution of optical isomers or purification of organic...
Patent
1987-10-08
1992-01-07
Rosen, Sam
Chemistry: molecular biology and microbiology
Process of utilizing an enzyme or micro-organism to destroy...
Resolution of optical isomers or purification of organic...
435106, 435128, C12P 1304
Patent
active
050791672
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to a method of racemate resolution.
2. Brief Description of the Prior Art
The constantly increasing need for amino acids leads to the existing sources being extended and optimized and furthermore to new ways of synthesis being discovered. In the chemical syntheses generally racemates are formed which must be separated in further steps into the antipodes.
SUMMARY OF THE INVENTION
According to the invention a method is provided for racemate resolution of amino acid derivatives which proceeds from an amino acid carbamate racemate and enzymatically resolves said racemate.
The advantage of using amino acid carbamates for preparing optically active amino acids is that in the synthesis of the starting compounds it is not necessary to start from the corresponding amino acids but that amino acid precursor (for example alpha-halogen carboxylic acid) can be converted directly to the carbamates.
The method according to the invention for racemate resolution can also be applied to the norephedrine carbamate racemate. Norephedrine acts as sympathomimetic.
In the method according to the invention for example methyl carbamates with the methoxycarbonyl group may be used.
Advantageously a water-soluble amino acid carbamate racemate and/or the racemate of a naturally occurring amino acid is used.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS OF THE INVENTION
The method according to the invention may be carried out hydrolytically resolves one of the enantiomers of an amino acid carbamate racemate or norephedrine carbamate racemate and which has been found in a test for said enzyme activity, or (a).
In variant (b) the resolution may be carried out with the aid of the enzyme activity in the form of the culture medium of the microorganism according to variant (a), of the culture medium separated from the microorganism, an extract of the culture medium or an extract of the microorganism.
Suitable microorganisms can be obtained from soil samples. For the isolation for example soil samples may be used which have been treated with carbamates. It is easily conceivable that for example land which has been treated with carbamate pesticides such as Betanal or Unden, carbamate-decomposing microorganisms live which enjoy therein a selection advantage so that an enrichment of strains with the desired characteristics can occur.
In another embodiment the method according to the invention may also be carried out with the aid of an enzyme which hydrolytically resolves one of the enantiomers of an amino acid carbamate racemate or norephedrine carbamate racemate and which has been determined in a test for this enzyme activity.
Such enzymes can open up a wide area of new uses. Possible uses are conceivable in peptide synthesis where a mild splitting off of protective groups introduced, for example t-butyloxycarbonyl or benzoxycarbonyl groups is of great interest.
Finally, according to an embodiment of the method according to the invention racemate resolution is isolated and/or acid, enantiomeric to the formed amino acid and further forming in the racemate resolution is resolved in a manner familiar to one skilled in the art and the enantiomeric amino acid recovered.
In the following examples, for instance the following enzymatic racemate resolution will be described: CO.sub.2 +methanol shifted to the right or downwards so that both enantiomers can be recovered with high purity.
Below the invention will be explained in detail with the aid of experimental methods and examples.
Execution of a screening with soil samples
One gram soil sample was incubated in 100 ml minimum medium (M2) containing a carbamate derivative as sole C and N source at 27.degree. C. and 100 rpm in a rotary vibrator. After 48 h, with 1% (v/v) a further culture was inoculated into the same medium. For recovering single colonies a dilution series with sterile saline* was made. Aliquots are spread onto agar plates with the minimum medium (M2). The Petri dishes are incubated at 27.degree. C. f
REFERENCES:
patent: 4202943 (1980-05-01), Suhara et al.
Baker et al-Am. J. Enol. Viliculture-vol. 27 No. 1 (1976) pp. 12-14.
Suhara et al-Chem. Abst. vol. 102 (1985) p. 20,930 f.
Sambale et al-Chem. Abst. vol. 107 (1987) p. 231, 994w.
Baker et al-Chem Abst. vol. 85 (1976) p. 29884g.
Drauz Karlheinz
Hummel Werner
Kula Maria-Regina
Sambale Clemens
Degussa AG, Zweigniederlassung Wolfgang
Gesellschaft fur Biotechnologische Forschung mbH (GBF)
Rosen Sam
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