GB992132A - Polysaccharides and methods for their production - Google Patents
Polysaccharides and methods for their productionInfo
- Publication number
- GB992132A GB992132A GB18470/62A GB1847062A GB992132A GB 992132 A GB992132 A GB 992132A GB 18470/62 A GB18470/62 A GB 18470/62A GB 1847062 A GB1847062 A GB 1847062A GB 992132 A GB992132 A GB 992132A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polysaccharide
- water
- phenol
- gives
- acid
- 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
Links
- 229920001282 polysaccharide Polymers 0.000 title abstract 6
- 239000005017 polysaccharide Substances 0.000 title abstract 6
- 150000004676 glycans Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 12
- 238000010521 absorption reaction Methods 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 150000004804 polysaccharides Chemical class 0.000 abstract 4
- 239000007787 solid Substances 0.000 abstract 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- 229960005486 vaccine Drugs 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 206010041925 Staphylococcal infections Diseases 0.000 abstract 2
- 241000191967 Staphylococcus aureus Species 0.000 abstract 2
- -1 amine salts Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 230000003053 immunization Effects 0.000 abstract 2
- 238000002649 immunization Methods 0.000 abstract 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- PZAGQUOSOTUKEC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.OS(O)(=O)=O PZAGQUOSOTUKEC-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 229920001284 acidic polysaccharide Polymers 0.000 abstract 1
- 150000004805 acidic polysaccharides Chemical class 0.000 abstract 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229960001950 benzethonium chloride Drugs 0.000 abstract 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000005119 centrifugation Methods 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 230000009918 complex formation Effects 0.000 abstract 1
- 238000000502 dialysis Methods 0.000 abstract 1
- 238000001962 electrophoresis Methods 0.000 abstract 1
- 238000004108 freeze drying Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- 229960003742 phenol Drugs 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 abstract 1
- 229940033663 thimerosal Drugs 0.000 abstract 1
- 238000004448 titration Methods 0.000 abstract 1
Classifications
-
- 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
- C12P21/00—Preparation of peptides or proteins
- C12P21/005—Glycopeptides, glycoproteins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/02—Bacterial antigens
- A61K39/085—Staphylococcus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/02—Bacterial antigens
- A61K39/09—Lactobacillales, e.g. aerococcus, enterococcus, lactobacillus, lactococcus, streptococcus
- A61K39/092—Streptococcus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Wood Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
The invention comprises a white, solid water-soluble, heat-stable, non-dialysable acidic polysaccharide of very high molecular weight and salts thereof, which contains, in free acid form, only the elements carbon, hydrogen, oxygen and nitrogen and is characterized by the following analytical data: [a ]23D=about - 79.4 degrees in water when dried to constant weight at 50 DEG C.; in free acid form shows infra-red absorption maxima at approximately 2.95, 3.22, 3.33, 3.37, 5.73, 6.00, 6.43, 6.96, 7.24, 7.61, 8.04, 8.77, 9.49, 10.83, 11.13 and 11.52 microns in a potassium bromide disc; gives negative Molisch and anthrone tests; on hydrolysis gives a positive Elson-Morgan test; by heating with diphenylamine in acetic acid-sulphuric acid mixture gives a blue solution showing an absorption maximum at 575 millimicrons; by heating in 79% sulphuric acid gives a solution having an ultra-violet absorption maximum at 290 millimicrons; by heating in acetic acid containing 10% sulphuric acid gives a solution having absorption maxima at 283, 410 and 470 millimicrons; moves towards the anode in electrophoresis at pH values of 4 and above and is detectable as a pink spot when sprayed with para-anisidine in butanol and sulphuric acid; and has a viscosity of about 0.0151 poises at 23 DEG C. (0.3% in water). The polysaccharide is prepared by heating, with dilute acetic acid, the phenol-insoluble, water-insoluble solid residue resulting from the extraction of strains of Staphylococcus aureus with phenol and an aqueous solvent. Preferably the solid is heated with 0.1 N acetic acid for 5 minutes under pressure at 121 DEG C. The aqueous phase, containing the polysaccharide is then separated by e.g. centrifugation. The free-acid polysaccharide may be isolated by dialysis and freeze-drying and purified by means of chromatography or complex-formation. The free acid may be converted to e.g. sodium, potassium, calcium, magnesium, ammonium and amine salts by titration with appropriate bases. Aqueous solutions of the polysaccharide or salts thereof are used as vaccines for immunization against staphylococcal infections (see Division A5).ALSO:Vaccines for immunization against staphylococcal infection comprise aqueous solutions of a nitrogen-containing polysaccharide obtained by acetic acid hydrolysis of the phenol-insoluble, water-insoluble solid residue resulting after extraction of strains of staphylococcus aureus with phenol and water (Division C3). The vaccine may be rendered isotonic, e.g. by addition of sodium chloride, and may be sterilized by means of heat, ultraviolet irradiation or by addition of preservatives, e.g. thimerosal, benzethonium chloride or phenol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10997861A | 1961-05-15 | 1961-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB992132A true GB992132A (en) | 1965-05-19 |
Family
ID=22330610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18470/62A Expired GB992132A (en) | 1961-05-15 | 1962-05-14 | Polysaccharides and methods for their production |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH417852A (en) |
| DE (1) | DE1185335B (en) |
| DK (1) | DK105490C (en) |
| FI (1) | FI40107C (en) |
| FR (1) | FR2679M (en) |
| GB (1) | GB992132A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2468372A1 (en) * | 1977-09-30 | 1981-05-08 | Yoshida Kosaku | NEW VACCINE AGAINST INFECTIOUS DISEASES IN BOVINE AND METHOD OF PRODUCING THE SAME |
| WO1999040440A1 (en) * | 1998-02-03 | 1999-08-12 | Bracco S.P.A. | Method for the determination of prosthetic infections |
| US20120282295A1 (en) * | 2009-10-30 | 2012-11-08 | Novartis Ag | Purification of staphylococcus aureus type 5 and type 8 capsular saccharides |
| CN112694541A (en) * | 2020-12-26 | 2021-04-23 | 成都大学 | Mild decoloring method for abelmoschus manihot polysaccharide |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1338879C (en) * | 1985-05-13 | 1997-01-28 | Commonwealth Scientific And Industrial Research Organisation | Mastitis vaccine |
-
1962
- 1962-05-14 GB GB18470/62A patent/GB992132A/en not_active Expired
- 1962-05-14 DK DK217262AA patent/DK105490C/en active
- 1962-05-14 DE DEP29409A patent/DE1185335B/en active Pending
- 1962-05-14 FI FI97262A patent/FI40107C/en active
- 1962-05-14 CH CH576762A patent/CH417852A/en unknown
- 1962-08-13 FR FR906872A patent/FR2679M/en active Active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2468372A1 (en) * | 1977-09-30 | 1981-05-08 | Yoshida Kosaku | NEW VACCINE AGAINST INFECTIOUS DISEASES IN BOVINE AND METHOD OF PRODUCING THE SAME |
| WO1999040440A1 (en) * | 1998-02-03 | 1999-08-12 | Bracco S.P.A. | Method for the determination of prosthetic infections |
| JP2010145416A (en) * | 1998-02-03 | 2010-07-01 | Bracco Spa | Method for the determination of prosthetic infections |
| US7807395B2 (en) | 1998-02-03 | 2010-10-05 | Bracco S.P.A. | Method for the determination of prosthetic infections |
| US20120282295A1 (en) * | 2009-10-30 | 2012-11-08 | Novartis Ag | Purification of staphylococcus aureus type 5 and type 8 capsular saccharides |
| US9060965B2 (en) * | 2009-10-30 | 2015-06-23 | Glaxosmithkline Biologicals Sa | Purification of Staphylococcus aureus type 5 capsular saccharides |
| US9441004B2 (en) | 2009-10-30 | 2016-09-13 | Glaxosmithkline Biologicals Sa | Purification of staphylococcus aureus type 8 capsular saccharides |
| US11208424B2 (en) | 2009-10-30 | 2021-12-28 | Glaxosmithkline Biologicals Sa | Staphylococcus aureus type 5 capsular saccharides |
| CN112694541A (en) * | 2020-12-26 | 2021-04-23 | 成都大学 | Mild decoloring method for abelmoschus manihot polysaccharide |
Also Published As
| Publication number | Publication date |
|---|---|
| FI40107C (en) | 1968-10-10 |
| DE1185335B (en) | 1965-01-14 |
| FR2679M (en) | 1964-07-27 |
| DK105490C (en) | 1966-10-03 |
| CH417852A (en) | 1966-07-31 |
| FI40107B (en) | 1968-06-28 |
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