FI83962B - Isolering av icke-reducerade oligosackarider. - Google Patents
Isolering av icke-reducerade oligosackarider. Download PDFInfo
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- FI83962B FI83962B FI863592A FI863592A FI83962B FI 83962 B FI83962 B FI 83962B FI 863592 A FI863592 A FI 863592A FI 863592 A FI863592 A FI 863592A FI 83962 B FI83962 B FI 83962B
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- Finland
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- process according
- oligosaccharides
- cellulose
- cellulose column
- Prior art date
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- 150000002482 oligosaccharides Chemical class 0.000 claims abstract description 80
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 54
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 45
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- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/005—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
-
- C—CHEMISTRY; METALLURGY
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catching Or Destruction (AREA)
- Polyesters Or Polycarbonates (AREA)
- Respiratory Apparatuses And Protective Means (AREA)
- Noodles (AREA)
- Spark Plugs (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Claims (17)
1. Förfarande för isolering av icke-reducerade oli-gosackarider frÀn ett glykoprotein eller glykohormon med 5 en N-förbunden oligosackaridstruktur, kÀnneteck-n a t dÀrav, att det omfattar följande steg: a) hydrazinolys av glykoproteinet eller glykohor-monet genom uppvÀrmning av det vÀsentligen vattenfria och vÀsentligen saltfria glykoproteinet eller glykohormonet i 10 nÀrvarande av vÀsentligen vattenfritt hydrazin under reaktionsbetingelser, vilka Àr tillrÀckliga att förorsaka spjÀlkning vid N-bindningsstÀllena för producering av en blandning, vilken som huvudkomponent innehÀller ett de-N-acetylerat hydrazonderivat av en oligosackarid, 15 b) N-acetylering av hydrazonderivatet i punkt (a) med ett önskat acetylerande medel för bildande av ett N-acetylerat hydrazonderivat av oligosackariden, c) underkastande av hydrazonderivatet i punkt (b) för syrakatalys för producering av de icke-reducerade 20 oligosackariderna, d) underkastande av de icke-reducerade oligosackariderna i punkt (c) för cellulosakolonnkromatografisk be-handling för avlÀgsnande av föroreningarna och tillvara-tagande av de icke-reducerade oligosackariderna. 25
2. Förfarande enligt patentkravet 1, kÀnne- t e c k n a t dÀrav, att hydrazinolysen utförs genom stegvis uppvÀrmning av utgÀngsÀmnena frÀn en utgÀngstem-peratur av cirka rumstemperatur tili ett temperaturomrÀde av cirka 65-100eC under cirka 2-10 timmar. 30
3. Förfarande enligt patentkravet 1, kÀnne- t e c k n a t dÀrav, att det N-acetylerande medlet Àr Àttiksyraanhydrid.
4. Förfarande enligt patentkravet 1, kÀnne-t e c k n a t dÀrav, att syrakatalysen utförs genom an-35 vÀndning av ett starkt surt katjonbytesharts. 24 83962
5. Förfarande enligt patentkravet 4, kÀnne-t e c k n a t dÀrav, att katjonbyteshartset utgörs av ett tvÀrbundet styren/divinylbensen-harts, som innehÀller funktionella sulfonsyragrupper. 5
6. Förfarande enligt patentkravet 4, kÀnne- t e c k n a t dÀrav, att cellulosakolonnen fyllts med mikrokristallin cellulosa.
7. Förfarande enligt patentkravet 1, kÀnne-t e c k n a t dÀrav, att cellulosakolonnkromatografin 10 utförs genom att tvÀtta cellulosakolonnen med en extrak-tionslösning av butanol, etanol och vatten för avlÀgsnan-de av föroreningarna och dÀrefter med elueringslösningar av metanol och vatten för erhÀllande av de icke-reducera-de oligosackariderna. 15
8. Förfarande enligt patentkravet 7, kÀnne- t e c k n a t dÀrav, att förhÀllandet mellan butanol, etanol och vatten i extraktionslösningen, som anvÀnds i cellulosakolonnen, Àr cirka 4:1:1, berÀknat pd volymen.
9. Förfarande enligt patentkravet 7, kÀnne-20 tecknat dÀrav, att cirka 5-10 kolonnvolymer av extraktionslösning anvÀnds för cellulosakolonnen för av-lÀgsnande av föroreningarna.
10. Förfarande enligt patentkravet 7, kÀnne-tecknat dÀrav, att cirka en kolonnvolym av metanol 25 och sedan cirka 5 kolonnvolymer av destillerat vatten anvÀnds för cellulosakolonnen för eluering av de icke-redu-cerade oligosackariderna.
11. Förfarande enligt patentkravet 1 för isolering av icke-reducerade oligosackarider frdn ett glykoprotein 30 eller glykohormon med en N-förbunden oligosackaridstruk-tur, kÀnnetecknat dÀrav, att det omfattar följande steg: a) hydrazinolys av glykoproteinet eller glykohor-monet genom uppvÀrmning av det vÀsentligen vattenfria och 35 vÀsentligen saltfria glykoproteinet eller glykohormonet i 25 83962 nÀrvarande av vÀsentligen vattenfritt hydrazin tili en temperatur av cirka 65-100°C, varvid reaktionstiden Àr cirka 2-10 timmar, för spjÀlkning av N-bindningsstÀllena och för producering av en blandning, vilken som huvudkom-5 ponent innehÀller ett de-N-acetylerat hydrazonderivat av en oligosackarid, b) N-acetylering av hydrazonderivatet i punkt (a) genom att anvÀnda ett överskott av Àttiksyraanhydrid i nÀrvaro av en mÀttad NaHC03-lösning, varvid reaktions- 10 temperaturen i början Àr cirka 4°C och den höjs tili cirka 20-25°C, för bildande av ett N-acetylerat hydrazonderivat av oligosackariden, c) underkastande av hydrazonderivatet i punkt (b) för syrakatalys genom att bringa blandningen i kontakt med 15 ett surt katjonbytesharts, som bestÀr av ett tvÀrbundet styren/divinylbensen-harts med funktionella sulfonsyra-grupper, för ersÀttning av Na*-joner med H*-joner och producering av de icke-reducerade oligosackariderna, d) underkastande av de i punkt (c) erhÀllna icke- 20 reducerade oligosackariderna för cellulosakolonnkromato- grafisk behandling genom att tvÀtta cellulosakolonnen med en extraktionslösning av butanol, etanol och vatten för avlÀgsnande av föroreningarna och dÀrefter genom att tvÀtta med elueringslösningar av metanol och vatten för 25 tillvaratagande av de icke-reducerade oligosackariderna.
12. Förfarande enligt patentkravet 11, kÀnne-t e c k n a t dÀrav, att hydrazinolysen utförs genom stegvis uppvÀrmning av utgÀngsÀmnena frÀn en utgÀngstem-peratur av cirka rumstemperatur genom att höja temperatu- 30 ren med cirka 10°C per timme.
13. Förfarande enligt patentkravet 11, kÀnne-t e c k n a t dÀrav, att cellulosakolonnen fyllts med mikrokristallin cellulosa.
14. Förfarande enligt patentkravet 11, kÀnne-35 tecknat dÀrav, att förhÀllandet mellan butanol, 26 83962 etanol och vatten i extraktionslösningen, sora anvÀnds i cellulosakolonnen, Àr cirka 4:1:1, berÀknat pÀ volymen.
15. Förfarande enligt patentkravet 11, kÀnne-t e c k n a t dÀrav, att cirka 5-10 kolonnvolymer av ex- 5 traktionslösning anvÀnds för cellulosakolonnen för avlÀgs-nande av föroreningarna.
16. Förfarande enligt patentkravet 11, kÀnne-t e c k n a t dÀrav, att en kolonnvolym av metanol och dÀrefter cirka 5 kolonnvolymer av destillerat vatten anvÀ- 10 nds för cellulosakolonnen för eluering av de icke-reduce-rade oligosackariderna.
17. Förfarande enligt patentkravet 16, kÀnne-t e c k n a t dÀrav, att en kolonnvolym av metanol och dÀrefter cirka 5 kolonnvolymer av destillerat vatten an- 15 vÀnds för cellulosakolonnen för eluering av de icke-re-ducerade oligosackariderna.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77298885 | 1985-09-06 | ||
| US06/772,988 US4719294A (en) | 1985-09-06 | 1985-09-06 | Isolation of unreduced oligosaccharides |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI863592A0 FI863592A0 (fi) | 1986-09-05 |
| FI863592A FI863592A (fi) | 1987-03-07 |
| FI83962B true FI83962B (fi) | 1991-06-14 |
| FI83962C FI83962C (sv) | 1991-09-25 |
Family
ID=25096828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI863592A FI83962C (sv) | 1985-09-06 | 1986-09-05 | Isolering av icke-reducerade oligosackarider |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US4719294A (sv) |
| EP (1) | EP0215766B1 (sv) |
| JP (1) | JPS6263524A (sv) |
| AT (1) | ATE68213T1 (sv) |
| AU (1) | AU580686B2 (sv) |
| CA (1) | CA1266265C (sv) |
| DE (1) | DE3681865D1 (sv) |
| DK (1) | DK425186A (sv) |
| FI (1) | FI83962C (sv) |
| GR (1) | GR862279B (sv) |
| IE (1) | IE59088B1 (sv) |
| IL (1) | IL79953A0 (sv) |
| NO (1) | NO164478C (sv) |
| ZA (1) | ZA866774B (sv) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3528654A1 (de) * | 1985-08-09 | 1987-02-19 | Hoechst Ag | Verfahren zur herstellung von alkylierten hydroxylgruppenfreien glycosylfluoriden |
| US4719294A (en) * | 1985-09-06 | 1988-01-12 | Monsanto Company | Isolation of unreduced oligosaccharides |
| JPH01502266A (ja) * | 1986-12-11 | 1989-08-10 | ăžă§ăłăžă ă»ăłăŒăăŹăŒă·ă§ăł | ïŒâăąăăâïŒâăăȘăă·ăȘăȘăŽçłăšăăźèȘć°äœăźèŁœé |
| US5324828A (en) * | 1986-12-11 | 1994-06-28 | Genzyme Corporation | 1-amino-1-deoxyoligosaccharides and derivatives thereof |
| US5344870A (en) * | 1987-12-02 | 1994-09-06 | Alberta Research Council | Sialic acid glycosides, antigens, immunoadsorbents, and methods for their preparation |
| US5079353A (en) * | 1987-12-02 | 1992-01-07 | Chembiomed, Ltd. | Sialic acid glycosides, antigens, immunoadsorbents, and methods for their preparation |
| DE3923365A1 (de) * | 1989-07-14 | 1991-01-24 | Suedzucker Ag | Oligosaccharidalditole mit amidbindung sowie verfahren zu ihrer herstellung |
| EP0462794B1 (en) * | 1990-06-21 | 1998-09-09 | Oxford GlycoSciences (UK) Limited | Automated process equipment for cleavage of biomolecules |
| GB9013828D0 (en) * | 1990-06-21 | 1990-08-15 | Oxford Glycosystems Ltd | Release and isolation of unreduced'n-and o-linked type'oligosaccharides |
| US5422079A (en) * | 1990-06-21 | 1995-06-06 | Oxford Glycosystems Limited | Automated process equipment |
| GB9013830D0 (en) * | 1990-06-21 | 1990-08-15 | Oxford Glycosystems Ltd | Release and isolation of unreduced'o-linked type'oligosaccharides |
| GB9013831D0 (en) * | 1990-06-21 | 1990-08-15 | Oxford Glycosystems Ltd | Release and isolation of unreduced'n-linked type'oligosaccharides |
| EP0462795A3 (en) * | 1990-06-21 | 1993-02-24 | Oxford Glycosystems Limited | Isolation of glycans |
| CA2136070C (en) * | 1992-06-01 | 1997-06-03 | Brad K. Bendiak | Sequential removal of monosaccharides from the reducing end of oligosaccharides and uses thereof |
| US5411892A (en) * | 1993-08-13 | 1995-05-02 | University Of Washington | Method and apparatus for carbohydrate analysis |
| US5585473A (en) * | 1994-12-09 | 1996-12-17 | The Biomembrane Institute | Compounds and methods for monosaccharide analysis |
| WO2002012254A1 (fr) * | 2000-08-02 | 2002-02-14 | Takara Bio Inc. | Procede de production de derives d'hydrazino monosaccharide et utilisation correspondante |
| US20040096948A1 (en) * | 2002-11-15 | 2004-05-20 | Yunping Huang | Glycoprotein cleavage protocol for oligosaccharide analysis |
| US20040096933A1 (en) * | 2002-11-15 | 2004-05-20 | Yunping Huang | Method of preparation of oligosaccharides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4362720A (en) * | 1977-04-14 | 1982-12-07 | Chembiomed Ltd. | Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals |
| US4719294A (en) * | 1985-09-06 | 1988-01-12 | Monsanto Company | Isolation of unreduced oligosaccharides |
-
1985
- 1985-09-06 US US06/772,988 patent/US4719294A/en not_active Expired - Lifetime
-
1986
- 1986-09-05 GR GR862279A patent/GR862279B/el unknown
- 1986-09-05 CA CA517634A patent/CA1266265C/en not_active Expired
- 1986-09-05 AT AT86870123T patent/ATE68213T1/de not_active IP Right Cessation
- 1986-09-05 AU AU62358/86A patent/AU580686B2/en not_active Ceased
- 1986-09-05 DE DE8686870123T patent/DE3681865D1/de not_active Expired - Lifetime
- 1986-09-05 EP EP86870123A patent/EP0215766B1/en not_active Expired - Lifetime
- 1986-09-05 FI FI863592A patent/FI83962C/sv not_active IP Right Cessation
- 1986-09-05 IL IL79953A patent/IL79953A0/xx not_active IP Right Cessation
- 1986-09-05 JP JP61209417A patent/JPS6263524A/ja active Granted
- 1986-09-05 DK DK425186A patent/DK425186A/da not_active Application Discontinuation
- 1986-09-05 NO NO863564A patent/NO164478C/no unknown
- 1986-09-05 IE IE237186A patent/IE59088B1/en not_active IP Right Cessation
- 1986-09-05 ZA ZA866774A patent/ZA866774B/xx unknown
- 1986-11-12 US US06/929,962 patent/US4736022A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ZA866774B (en) | 1987-07-29 |
| NO863564L (no) | 1987-03-09 |
| US4719294A (en) | 1988-01-12 |
| NO863564D0 (no) | 1986-09-05 |
| US4736022A (en) | 1988-04-05 |
| DE3681865D1 (de) | 1991-11-14 |
| IL79953A0 (en) | 1986-12-31 |
| FI863592A0 (fi) | 1986-09-05 |
| JPS6263524A (ja) | 1987-03-20 |
| IE862371L (en) | 1987-03-06 |
| NO164478B (no) | 1990-07-02 |
| EP0215766A3 (en) | 1988-07-27 |
| IE59088B1 (en) | 1994-01-12 |
| EP0215766B1 (en) | 1991-10-09 |
| DK425186D0 (da) | 1986-09-05 |
| EP0215766A2 (en) | 1987-03-25 |
| DK425186A (da) | 1987-03-07 |
| AU580686B2 (en) | 1989-01-27 |
| GR862279B (en) | 1987-01-12 |
| NO164478C (no) | 1990-10-10 |
| FI83962C (sv) | 1991-09-25 |
| JPH0579079B2 (sv) | 1993-11-01 |
| AU6235886A (en) | 1987-03-12 |
| CA1266265A (en) | 1990-02-27 |
| ATE68213T1 (de) | 1991-10-15 |
| CA1266265C (en) | 1990-02-27 |
| FI863592A (fi) | 1987-03-07 |
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| Date | Code | Title | Description |
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| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: MONSANTO COMPANY |