SE454357B - Forfarande for framstellning av maltoheptaosderivat - Google Patents
Forfarande for framstellning av maltoheptaosderivatInfo
- Publication number
- SE454357B SE454357B SE8400206A SE8400206A SE454357B SE 454357 B SE454357 B SE 454357B SE 8400206 A SE8400206 A SE 8400206A SE 8400206 A SE8400206 A SE 8400206A SE 454357 B SE454357 B SE 454357B
- Authority
- SE
- Sweden
- Prior art keywords
- derivatives
- procedure
- maltoheptaos
- preparing
- phenylglucoside
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- NEZJDVYDSZTRFS-RMPHRYRLSA-N Phenyl beta-D-glucopyranoside Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1 NEZJDVYDSZTRFS-RMPHRYRLSA-N 0.000 claims description 5
- 241000178960 Paenibacillus macerans Species 0.000 claims description 3
- 239000004382 Amylase Substances 0.000 description 2
- 102000013142 Amylases Human genes 0.000 description 2
- 108010065511 Amylases Proteins 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 2
- 235000019418 amylase Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 dinitrophenyl residues Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 101000935015 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) N-acetyl-6-hydroxytryptophan oxidase ivoB Proteins 0.000 description 1
- 239000001116 FEMA 4028 Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 102000006995 beta-Glucosidase Human genes 0.000 description 1
- 108010047754 beta-Glucosidase Proteins 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
- C12Q1/40—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase involving amylase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
- C12Q2334/10—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases p-Nitrophenol derivatives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/805—Test papers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/81—Packaged device or kit
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Description
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454 357 2
Användbara är emellertid även i ß-ställning stående substi-
tuenter. I sistnämnda fall användes dessutom förutom OC-gluko-
sidas jämväl ß-glukosidas.
Vid dinitrofenylrester kan de båda nitrogrupperna förefin-
nas i godtycklig ställning, exempelvis som 2,4-, 2,6- eller
3,5-substituenter.
De vid avspjälkningen av nitrogrupper innehållande substi-
tuenter frigjorda nitrofenolerna resp. dinitrofenolerna är själva
färgade föreningar, som utan vidare kan bestämmas optískt. Av-
spjälkas fenol som sådan, sä kan denna bestämmas enligt kända
metoder, exempelvis genom omsättning med ett nukleofílt reagens,
såsom 3-metyl-6-sulfonyl-benstiazolon-hydrazon-(2) (HSK) i när-
varo av monofenoloxidas. Vid denna reaktion bildas ett rött
färgämne, som kan mätas. De för detta ändamål använda malto-
heptaosderivaten framställes enligt uppfinningen genom ett för-
farande, som kännetecknas därav, att fenylglukosid resp. nítrerad
fenylglukosid bringas att reagera med M-cyklodextrin i närvaro
av Bacillus macerans amylas E.C.2.4.1.19. I den enligt uppfin-
ningen genomförda.transglukosideringen användes den kända amylasen
från Bacillus macerans [E.C. 2.4.1.19. DSM 24; isolering: J.A.
de Pinto, L.L. Cambell, Biochemistry 1, 114 (1968); Transfer-
reaction: Methods in Carbohydr. Chemistry, vol II, 3471].
Följande exempel åskådliggör uppfinningen._
Exempel
p-nítrofenyl- - maltooligosackarid genom enzymatisk
syntes med Bac. maeerans-amylas
(E.C.2.4.1.19 ur Bac. macerans DSM 24)
Bacillus macerans-amylas har förutom hydrolytisk och cyk-
liserande verkan även glukosyl-transfererande egenskaper, vilka
kan användas för syntes av olígosackarider och -derivat (Methods
in Carbohydrate Chemistry II, 347). För syntesen av p-nitro-
fenyl-oligosackarider optimerades detta förfarande på följande
sätt:
680 mg Bacillus macerans-amylas (E.C.2.4.1.19 ur Bac.
macerans DSM 24) Clyofilisat) (0,46 U/mg invägning, proteinhalt
av invägningen 28,5%, fri från p-nitrofenyl- -D-glukosid-spjä1-
kande aktiviteter),
400 mg 0eD-p-nitrofenylglukosid,
3,5 g oecyklodextrin, och
70 ml Sörensen-fosfatbuffert, pH 6,2; 0,01 M blandades.
3 454 ss?
.p
Satsen ínkuberades 24 h vid 37°C. För rening separerades därpå
ol- och bildad ß-cyklodextrin närmast över tetrakloretylen-ínne-
slutningsföreníng. Efter kromatografi medelst tvärbindningsbun-
det dextrans ("Sephadex LI-I20") erhölls 50 mg lyofílísat av i amy-
lastest högaktiv p-nítrofenyl-maltoheptaosid.
Claims (1)
- 454- 357 _ Patentkrav Förfarande för framställning av ett mnltohaptaosderivat med den allmänna formeln I: cnzon. - cnzofl i o f, R I s m; 0 ou 0 no on OH l l vari R betecknar en fenylglukosid-, mononitrofenylglukosid- eller dínitrofenylglukoaidgrupp, k ä n n e Q e c k n a t därav, att fenylglukosid resp. nitrerad fenylglukosid bringa: att reagera madtï-cyklodextrin i närvaro av Bacillus macerans amylns E.C.2.4.1.19.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2741192A DE2741192C2 (de) | 1977-09-13 | 1977-09-13 | Verfahren zur Bestimmung von alpha- Amylase |
| DE19772755803 DE2755803A1 (de) | 1977-12-14 | 1977-12-14 | Verfahren und reagens zur bestimmung von alpha-amylase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8400206D0 SE8400206D0 (sv) | 1984-01-17 |
| SE8400206L SE8400206L (sv) | 1984-01-17 |
| SE454357B true SE454357B (sv) | 1988-04-25 |
Family
ID=25772710
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7809278A SE433857B (sv) | 1977-09-13 | 1978-09-04 | Forfarande och reagens for bestemning av alfa-amylas |
| SE8400206A SE454357B (sv) | 1977-09-13 | 1984-01-17 | Forfarande for framstellning av maltoheptaosderivat |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7809278A SE433857B (sv) | 1977-09-13 | 1978-09-04 | Forfarande och reagens for bestemning av alfa-amylas |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US4544631A (sv) |
| JP (1) | JPS5451892A (sv) |
| AR (1) | AR217476A1 (sv) |
| AT (1) | AT362526B (sv) |
| AU (1) | AU521908B2 (sv) |
| CA (1) | CA1120836A (sv) |
| CH (1) | CH651590A5 (sv) |
| CS (1) | CS236765B2 (sv) |
| DD (1) | DD138921A5 (sv) |
| DK (1) | DK153335C (sv) |
| ES (2) | ES473296A1 (sv) |
| FI (1) | FI61916C (sv) |
| FR (1) | FR2402872A1 (sv) |
| GB (2) | GB2004646B (sv) |
| HK (1) | HK54785A (sv) |
| HU (1) | HU182005B (sv) |
| IE (1) | IE47953B1 (sv) |
| IL (2) | IL55408A (sv) |
| IT (1) | IT1099451B (sv) |
| LU (1) | LU80213A1 (sv) |
| MY (1) | MY8600101A (sv) |
| NL (1) | NL190818C (sv) |
| SE (2) | SE433857B (sv) |
| SG (1) | SG21085G (sv) |
| YU (1) | YU44180B (sv) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741192C2 (de) * | 1977-09-13 | 1982-07-01 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur Bestimmung von alpha- Amylase |
| JPS60997B2 (ja) * | 1978-01-31 | 1985-01-11 | 東洋紡績株式会社 | アミラ−ゼ活性測定法 |
| EP0048035B1 (en) * | 1978-06-06 | 1983-12-07 | Flow General, Inc. | Maltodextrin phosphorylase limit dextrin and method of producing it |
| JPS5768798A (en) * | 1980-10-14 | 1982-04-27 | Toyo Jozo Co Ltd | Novel measurement of amylase activity |
| DE3372774D1 (en) * | 1982-09-16 | 1987-09-03 | Wako Pure Chem Ind Ltd | Modified oligosaccharides used as substrate for measuring alpha-amylase activity |
| DE3323245A1 (de) * | 1983-06-28 | 1985-01-10 | Merck Patent Gmbh, 6100 Darmstadt | Verfahren und reagenz zur bestimmung von (alpha)-amylase |
| DE3328616A1 (de) * | 1983-08-08 | 1985-02-28 | Boehringer Mannheim Gmbh, 6800 Mannheim | Oligoglucosidderivate |
| JPS60114193A (ja) * | 1983-11-22 | 1985-06-20 | Toyo Jozo Co Ltd | 新規なマルトースデヒドロゲナーゼおよびその製法それを用いる分析法 |
| US4649108A (en) * | 1984-07-26 | 1987-03-10 | Genzyme Corporation | Alpha amylase assay |
| US4794078A (en) * | 1984-07-26 | 1988-12-27 | Genzyme Corporation | Alpha amylase assay |
| JPS6183195A (ja) * | 1984-08-24 | 1986-04-26 | Wako Pure Chem Ind Ltd | 新規なオリゴサツカライド誘導体、及びこれを基質として用いるα−アミラ−ゼ活性測定法 |
| JPS61124397A (ja) * | 1984-11-22 | 1986-06-12 | Toyobo Co Ltd | α−アミラ−ゼの活性測定用試薬 |
| DE3508384A1 (de) * | 1985-03-08 | 1986-11-06 | Boehringer Mannheim Gmbh, 6800 Mannheim | Hemmung humaner speichel- und pankreasamylase durch monoklonale antikoerper |
| SE451849B (sv) * | 1985-12-11 | 1987-11-02 | Svenska Sockerfabriks Ab | Sett att syntetisera glykosidiska bindningar samt anvendning av pa detta sett erhallna produkter |
| US4782018A (en) * | 1986-01-17 | 1988-11-01 | Eastman Kodak Company | Detection of hydrolyzing enzymes |
| DE3621271A1 (de) * | 1986-06-25 | 1988-01-07 | Boehringer Mannheim Gmbh | Verfahren und reagenz zur bestimmung von alpha-amylase |
| US5158872A (en) * | 1986-10-07 | 1992-10-27 | Hoechst Celanese Corporation | Aromatic substituted glycoside |
| US4963479A (en) * | 1986-10-07 | 1990-10-16 | Hoechst Celanese Corporation | Reagent system for an alpha-amylase assay containing aromatic substituted glycoside |
| WO1989000600A1 (en) * | 1987-07-17 | 1989-01-26 | Ivan Endre Modrovich | Stable, single-liquid alpha-amylase reagent |
| US4932871A (en) * | 1987-11-20 | 1990-06-12 | Miles Inc. | Rapid method for preparing chromogenic alpha-amylase substrate compounds at high preparative yields |
| DE3743908A1 (de) * | 1987-12-23 | 1989-07-06 | Boehringer Mannheim Gmbh | Neue oligoglucoside |
| DE3929355A1 (de) * | 1989-09-04 | 1991-03-07 | Boehringer Mannheim Gmbh | Verfahren zur spezifischen bestimmung von pankreas-(alpha)-amylase |
| JP2576910B2 (ja) * | 1990-04-13 | 1997-01-29 | 富士写真フイルム株式会社 | 免疫分析要素および免疫分析方法 |
| US5300634A (en) * | 1991-05-07 | 1994-04-05 | Wako Pure Chemical Industries, Ltd. | Process for producing maltooligosaccharide derivative |
| JP3075377B2 (ja) * | 1991-11-06 | 2000-08-14 | 東洋紡績株式会社 | α−アミラーゼ活性の測定法およびα−アミラーゼ活性測定用試薬 |
| ES2183585T3 (es) * | 1998-07-24 | 2003-03-16 | Samsung Fine Chemicals Co Ltd | Procedimiento para la preparacion de derivados de (s) -3-4-dihidroxibutirico opticamente puros. |
| KR100374358B1 (ko) * | 2000-07-13 | 2003-03-04 | 주식회사 코메드 | 미생물 동정을 위한 비피검사법과 구연산염 검사법을대체하는 글루코시드 분해검사배지와 셀로비오스분해검사배지 및 그 검사법 |
| US20040096948A1 (en) * | 2002-11-15 | 2004-05-20 | Yunping Huang | Glycoprotein cleavage protocol for oligosaccharide analysis |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT986838B (it) * | 1972-05-12 | 1975-01-30 | Sclavo Inst Sieroterapeut | Complesso di reagenti per la deter minazione enzimatica del glucosio sistema glucosio ossidasi perossi dasi con metodo manuale e automati co con lettura a termine o in cinetica |
| US3879263A (en) * | 1973-09-06 | 1975-04-22 | Du Pont | Method for the determination of amylase |
| US4000042A (en) * | 1973-09-06 | 1976-12-28 | E. I. Du Pont De Nemours And Company | Diagnostic reagent for the determination of amylase |
| US3867259A (en) * | 1973-11-08 | 1975-02-18 | American Cyanamid Co | Lactate dehydrogenase test material |
| DE2600526C3 (de) * | 1976-01-08 | 1981-06-19 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur quantitativen Bestimmung von mit Sauerstoff unter Oxidaseeinwirkung H↓2↓O↓2↓ bildenden Substanzen und Reagens zu seiner Durchführung |
| US4097336A (en) * | 1976-02-13 | 1978-06-27 | Beckman Instruments, Inc. | Reagent system for beta-amylase assay |
| US4036697A (en) * | 1976-02-13 | 1977-07-19 | Beckman Instruments, Inc. | Kinetic assay for alpha-amylase |
| US4059407A (en) * | 1976-04-14 | 1977-11-22 | Becton, Dickinson And Company | Disposable chemical indicators |
| CA1104912A (en) * | 1976-07-13 | 1981-07-14 | Robert C. Menson | Method and test kit for serum amylase assay |
| CA1096376A (en) * | 1976-07-13 | 1981-02-24 | William B. Farnham | Process for preparing nitroaromatic glycosides |
| US4081326A (en) * | 1976-10-07 | 1978-03-28 | The Board Of Trustees Of The University Of Alabama | A method for removing maltotetraose and lower saccharides from solution |
| US4071407A (en) * | 1976-11-16 | 1978-01-31 | The Board Of Trustees Of The University Of Alabama | Novel maltase enzyme produced by a new yeast strain |
| US4102747A (en) * | 1977-07-28 | 1978-07-25 | American Hospital Supply Corporation | Amylase determination |
| DE2748036C2 (de) * | 1977-10-26 | 1986-08-21 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur Gewinnung von Maltose-phosphorylase oder/und β-Phosphoglucose-mutase und Verwendung derselben |
| US4233403A (en) * | 1978-02-27 | 1980-11-11 | E. I. Du Pont De Nemours And Company | Amylase assay |
| US4219571A (en) * | 1978-06-15 | 1980-08-26 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing a sweetener |
| US4225672A (en) * | 1979-02-27 | 1980-09-30 | Hall Leo M | Method for producing maltooligosaccharide glycosides |
| US4932871A (en) * | 1987-11-20 | 1990-06-12 | Miles Inc. | Rapid method for preparing chromogenic alpha-amylase substrate compounds at high preparative yields |
-
1978
- 1978-08-14 AT AT589778A patent/AT362526B/de not_active IP Right Cessation
- 1978-08-16 CA CA000309495A patent/CA1120836A/en not_active Expired
- 1978-08-17 NL NL7808528A patent/NL190818C/xx not_active IP Right Cessation
- 1978-08-22 IL IL55408A patent/IL55408A/xx active IP Right Grant
- 1978-08-23 DK DK372178A patent/DK153335C/da not_active IP Right Cessation
- 1978-08-29 AR AR273483A patent/AR217476A1/es active
- 1978-08-30 IT IT27180/78A patent/IT1099451B/it active
- 1978-09-04 SE SE7809278A patent/SE433857B/sv not_active IP Right Cessation
- 1978-09-06 GB GB7835813A patent/GB2004646B/en not_active Expired
- 1978-09-06 GB GB8033088A patent/GB2058780B/en not_active Expired
- 1978-09-08 FR FR7825964A patent/FR2402872A1/fr active Granted
- 1978-09-11 DD DD78207746A patent/DD138921A5/xx unknown
- 1978-09-11 LU LU80213A patent/LU80213A1/de unknown
- 1978-09-11 AU AU39750/78A patent/AU521908B2/en not_active Expired
- 1978-09-11 CH CH9494/78A patent/CH651590A5/de not_active IP Right Cessation
- 1978-09-12 YU YU2162/78A patent/YU44180B/xx unknown
- 1978-09-12 HU HU78BO1734A patent/HU182005B/hu unknown
- 1978-09-12 IE IE1838/78A patent/IE47953B1/en not_active IP Right Cessation
- 1978-09-12 FI FI782789A patent/FI61916C/fi not_active IP Right Cessation
- 1978-09-13 JP JP11183678A patent/JPS5451892A/ja active Granted
- 1978-09-13 ES ES473296A patent/ES473296A1/es not_active Expired
-
1979
- 1979-04-27 ES ES480028A patent/ES480028A1/es not_active Expired
- 1979-11-29 CS CS798241A patent/CS236765B2/cs unknown
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1981
- 1981-05-21 IL IL62923A patent/IL62923A0/xx unknown
- 1981-10-16 US US06/311,856 patent/US4544631A/en not_active Expired - Lifetime
-
1984
- 1984-01-17 SE SE8400206A patent/SE454357B/sv not_active IP Right Cessation
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1985
- 1985-03-21 SG SG210/85A patent/SG21085G/en unknown
- 1985-07-18 HK HK547/85A patent/HK54785A/xx not_active IP Right Cessation
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1986
- 1986-12-30 MY MY101/86A patent/MY8600101A/xx unknown
-
1990
- 1990-06-27 US US07/545,092 patent/US5108913A/en not_active Expired - Fee Related
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