GB762976A - Erythromycin b and acid addition salts thereof - Google Patents

Erythromycin b and acid addition salts thereof

Info

Publication number
GB762976A
GB762976A GB1867/54A GB186754A GB762976A GB 762976 A GB762976 A GB 762976A GB 1867/54 A GB1867/54 A GB 1867/54A GB 186754 A GB186754 A GB 186754A GB 762976 A GB762976 A GB 762976A
Authority
GB
United Kingdom
Prior art keywords
erythromycin
nrrl
solvent
culture medium
extraction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1867/54A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB762976A publication Critical patent/GB762976A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/44—Preparation of O-glycosides, e.g. glucosides
    • C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
    • C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
    • C12R2001/465—Streptomyces

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Molecular Biology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Erythromycin B is produced by cultivating an erythromycin - B - producing strain of Streptomyces erythreus in a culture medium containing an assimilable source of carbohydrate, nitrogen and inorganic salts under submerged aerobic conditions until substantial antibiotic activity is produced by said organism in said culture medium and extracting the filtered medium with a waterimmiscible polar solvent, removing the solvent and separating the erythromycin B by countercurrent extraction from any erythromycin present. Suitable micro-organisms are S. erythreus strains NRRL 2338 (preferred), NRRL 2359, NRRL 2360 and NRRL 2361. The culture medium and conditions of culture are similar to those employed in Specification 708,159 for the preparation of erythromycin per se. Specified water-immiscible polar solvents are alkyl esters of fatty acids, e.g. ethyl acetate and amyl acetate; chlorinated hydrocarbons, e.g. chloroform and ethylene dichloride; alcohols, e.g. butanol and pentanol; ketones, e.g. methyl amyl ketone, ethyl ether and dibutyl ether. Preferably the filtered broth is adjusted to at least pH 9.5 before extraction with the polar solvent. Erythromycin B is separated from erythromycin by (a) adsorption and e.g. purified cellulose fibre followed by selective elution with e.g. aqueous ammonia saturated with methyl isobutyl ketone; or (b) extraction in a Craig countercurrent apparatus using as solvent a mixture of methyl isobutyl ketone, 0.1 M phosphate buffer at pH 6.5 and acetone. Erythromycin B is a nitrogenous base forming salts <FORM:0762976/IV(b)/1> <FORM:0762976/IV(b)/2> with acids; in 2 : 1 dimethylformamide-water solution pK1a of 8.5; molecular weight of about 736; infra-red absorption spectrum of chloroform solution shows absorption maxima at 2.80; 3.34; 5.80; 5.90; 6.84; 7.24; 7.50; 7.79; 8.04; 8.54; 8.98; 9.14; 9.48; 9.86; 10.24; 10.56; 10.96; 11.22; 11.54 and 11.94 microns. Specified salts are the hydrochloride, sulphate, citrate, mandelate, succinate, oleate, palmitate, myristate, stearate, oxalate, thiocyanate and glucoheptanate.
GB1867/54A 1953-07-29 1954-01-21 Erythromycin b and acid addition salts thereof Expired GB762976A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US762976XA 1953-07-29 1953-07-29

Publications (1)

Publication Number Publication Date
GB762976A true GB762976A (en) 1956-12-05

Family

ID=22131095

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1867/54A Expired GB762976A (en) 1953-07-29 1954-01-21 Erythromycin b and acid addition salts thereof

Country Status (1)

Country Link
GB (1) GB762976A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1266905A1 (en) * 2000-03-22 2002-12-18 Chugai Seiyaku Kabushiki Kaisha Process for producing purified erythromycin

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1266905A1 (en) * 2000-03-22 2002-12-18 Chugai Seiyaku Kabushiki Kaisha Process for producing purified erythromycin
EP1266905A4 (en) * 2000-03-22 2003-05-07 Chugai Pharmaceutical Co Ltd Process for producing purified erythromycin
US6767998B2 (en) 2000-03-22 2004-07-27 Chugai Seiyaku Kabushiki Kaisha Method for preparing purified erythromycin

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