Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Cyclic peptides
Patent
1986-02-06
1989-11-21
Moskowitz, Margaret
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Cyclic peptides
530333, 530344, 530335, 530336, C07K 750, C07K 100, C07K 114
Patent
active
048824194
DESCRIPTION:
BRIEF SUMMARY
Antibiotic L 17392 is an antibiotic substance which is obtained by removing all the sugar moieties from the glycopeptidic antibiotic teicoplanin. Teicoplanin is the international non-proprietary name (INN) of the antibiotic substance formerly named teichomycin which is obtained by cultivating the strain Actinoplanes teichomyceticus nov. sp. ATCC 31121 in a culture medium containing assimilable sources of carbon, nitrogen and inorganic salts (see U.S. Pat. No. 4,239,751). According to the procedure described in the above cited patent an antibiotic complex containing teichomycin A.sub.1, A.sub.2 and A.sub.3 is recovered from the separated fermentation broth by extraction with a suitable water insoluble organic solvent and precipitation from the extracting solvent according to common procedures. Teichomycin A.sub.2, which is the major factor of the isolated antibiotic complex, is then separated from the obtained antibiotic mixture by means of column chromatography on Sephadex.RTM..
PHYSICO-CHEMICAL CHARACTERISTICS OF CRYSTALLINE PURE ANTIBIOTIC L 17392
ethanol and acetone; slightly soluble in ethyl alcohol and dimethylformamide maxima: =87.1) =165.3) significant absorption maxima (cm.sup.-1): selective decoupling experiments of the .sup.1 H NMR spectrum registered at 270 MHz with a Bruker WH-270 Spectrometer, in DMSO-d.sub.6 at 50.degree. C. (internal standard TMS, .delta.=0.00 ppm) are as follows: (.delta., multiplicity): 5.14, d; 5.35, d; 5.56, d; 5.60, d; 6.3-7.9, m; 6.55, d; 7.37, d; 7.50, d; 7.61, d; 8.26, d; 8.28, d; 8.5-10.2, br; percentage composition (average): carbon 58.05%; hydrogen 3.58%; nitrogen 8.23%; chlorine 5.85%; (after correction for a weight loss of 11%, measured by thermal gravimetric analysis) pre-column (5 cm) packed with Perisorb RP-8 (30 .mu.m; Merck) followed by a column Hibar RT 250-4 (Merck) prepacked with LiChrosorb RP-8 (10 .mu.m) and eluting with a liner step-gradient ranging from 10% to 30% acetonitrile in 0.2% aqueous ammonium formate; flow rate: 2 ml/min. (internal standard: Teicoplanin A.sub.2 component 2 of U.K. Patent Application Publication 2121401, t.sub.R =22.4 min)
On the basis of the chemico-physical data the following formula may be attributed to antibiotic L 17392: ##STR2## A substance having the same structural formula is disclosed in European Patent Application No. 0098578 and is named antibiotic A 41030 factor B. This substance is obtained by mans of a microbiological process which involves the fermentation of the strain Streptomyces virginiae NRRL 12525 or Streptomyces virginiae NRRL 15156 in a suitable medium, the isolation, purification and separation into its components of antibiotic A 41030 factor B, included.
Antibiotic L 17392 possesses acid and basic functions capable of forming salts with bases and acids, respectively. The acid and/or basic salts of antibiotic L 17392 can be in general prepared according to known per se procedures.
These procedures includes reacting antibiotic L 17392 with at least a molar equivalent of the selected acid or base.
A preferred procedure for preparing a salt of antibiotic L 17392 with a base includes reacting antibiotic L 17392 and the base in about equimolecular amount in water, conveniently at room temperature, and lyophilizing the solution obtained at the end of the salification reaction.
A preferred procedure for preparing a salt of antibiotic L 17392 with an acid includes reacting antibiotic L 17392 with the selected acid in an aqueous lower alkanol, conveniently at room temperature. Then, the water is eliminated and the desired salt of antibiotic L 17392 is precipitated by adding a non-solvent, such as ethyl ether, to the organic phase. A preferred example of aqueous lower alkanol is a mixture of water and butanol. The preferred ratio water/butanol is about 30:70.
Representative examples of salts of antibiotic L 17392 with bases are the alkali metal, such as sodium or potassium, the ammonium and alkylammonium salts. These salts with bases encompass also the salts with basic amino acids such as lysine and arginine.
REFERENCES:
patent: 3960828 (1976-06-01), Meienhofer
patent: 4293490 (1981-10-01), Abbott et al.
patent: 4322343 (1982-03-01), Debono
patent: 4497802 (1985-02-01), Debono
Malabarba et al., Journal of Antibiotics, vol. XXXVII, No. 9, pp. 988-999, (911984).
Barna et al., Journal of Antibiotics, vol. XXXVII, No. 10, pp. 1204-1208, (10/1984).
Hunt et al., J. Am. Chem. Soc. vol. 106, No. 17, pp. 4891-4895, (8/22/84).
Barna et al., J. Am. Chem. Soc., vol. 106, No. 17, pp. 4895-4902, (8/22/84).
Cram et al., Organic Chemistry, Second Ed. McGraw-Hill Book Company, New York, P. 559 (1964).
Cavalleri Bruno
Malabarba Adriano
Strazzolini Paolo
Chan Christina
Gruppo Lepetit S.p.A.
Moskowitz Margaret
Nesbitt Stephen L.
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