Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1980-07-14
1983-05-10
Phillips, Delbert R.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
435 70, 435253, C07C10352, C12P 2102, C12N 120
Patent
active
043828884
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE ART
The present invention relates to a novel tryptophan derivative having an inhibitory activity against metallo proteinases, and a process for biochemically producing the tryptophan derivative. The novel metallo proteinase inhibitor is useful for medicine such as an agent for treating Pseudomonas aeruginosa infections disease and an agent for regulating growth of a microorganism. The microorganism for producing such derivative is Streptomyces mozunensis, which is a new species of the genus Streptomyces.
BACKGROUND OF THE ART
Proteinase inhibitors are useful in a medical field, and some of them are put to practical use. Particularly, it is thought that a metallo proteinase inhibitor can be used as an agent for treating Pseudomonas aeruginosa infectious disease. It is known that the metallo proteinase of Pseudomonas aeruginosa plays an important part for Pseudomonas aeruginosa infectious disease.
On the other hand, in a field of biochemistry, the material having inhibitory activity against a metallo proteinase produced by a microorganism, is useful. For example, it is expected that the material is used for regulating growth and metabolism of a microorganism.
Accordingly, it is significant in a field of medicine and biochemistry that a material inhibiting against the metallo proteinase produced by Pseudomonas aeruginosa is given.
Phosphoramidon (The Journal of Antibiotics 26, [10], 621 (1973) and S-MPI (Agric. Biol. Chem., 42, [4],899 (1978)) are known as a metallo proteinase inhibitor produced by the genus Streptomyces, and differ from the object compound of the present invention.
DISCLOSURE OF THE INVENTION
The present invention relates to a novel compound, N-(6-deoxy-L-talosyloxy hydroxyphosphinyl)-L-leucyl-L-tryptophan having the following structural formula: ##STR1## which hereinafter may be referred to as novel tryptophan derivative, and to a process for producing the novel tryptophan derivative which comprises culturing a microorganism belonging to the genus Streptomyces and capable of producing novel tryptophan derivative, which may be referred to as novel tryptophan derivative producing microorganism, producng the novel tryptophan derivative in the culture medium and recovering it.
The novel tryptophan derivative may be in the salt form and ester form. The hydroxyl group in the sugar moiety of the compound may be protected. The salt and ester thereof, wherein phosphoric acid residue and/or carboxyl group are modified, is within the present invention. Examples of the salt are metal salts such as sodium, potassium, rubidium, cesium, and calcium salt, and ammonium salt. Examples of the ester are alkyl, aryl and aralkyl ester such as methyl, ethyl, phenyl and benzyl ester.
As protecting group for hydroxyl group of the sugar moiety, one in common use as protecting group for hydroxyl group of the part of sugar mentioned above, for example, acyl group such as acetyl and benzoyl group can be used.
Novel tryptophan derivative can be produced by culturing novel tryptophan derivative producing microorganism and recovering the tryptophan derivative produced in the culture medium.
As liquid medium used in a culture of the microorganism, one in common use for culturing ordinary microorganism may be able to be used.
Carbon source which can be assimilated by novel tryptophan derivative producing microorganism, for example, carbohydrates such as glucose, galactose, maltose, starch and hydrolyzed starch, alcohol such as glycerol, nitrogen source, for example, ammonium salts such as ammonium sulfate and ammonium chloride, amino acids, peptone, meat extract, hydrolyzed soy bean, and inorganic salts, and materials containing minor nutrients, if necessary, may be used.
The microorganism may be cultured, for example, usually at pH 5.0 to 9.0, and at a temperature of 15.degree. to 40.degree. C. under aerobical condition such as shaking and airation with stirring.
The novel tryptophan derivative is produced in the culture medium of the novel tryptophan derivative producing microorganism and in the microo
REFERENCES:
Chem. Abstr. vol. 93, 1980, 219326q.
Fukuhara Kenichi
Murao Sawao
Ajinomoto Company Incorporated
Phillips Delbert R.
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