DE69429167T2 - Eine stabilisierte phenylalanin-ammonia-lyase - Google Patents
Eine stabilisierte phenylalanin-ammonia-lyaseInfo
- Publication number
- DE69429167T2 DE69429167T2 DE69429167T DE69429167T DE69429167T2 DE 69429167 T2 DE69429167 T2 DE 69429167T2 DE 69429167 T DE69429167 T DE 69429167T DE 69429167 T DE69429167 T DE 69429167T DE 69429167 T2 DE69429167 T2 DE 69429167T2
- Authority
- DE
- Germany
- Prior art keywords
- pal
- bis
- enzyme preparation
- preparation according
- enzyme
- 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 - Lifetime
Links
- 108700023158 Phenylalanine ammonia-lyases Proteins 0.000 title claims abstract description 44
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 102000004190 Enzymes Human genes 0.000 claims description 30
- 108090000790 Enzymes Proteins 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 18
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical group O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000002775 capsule Substances 0.000 claims description 4
- 239000002702 enteric coating Substances 0.000 claims description 4
- 238000009505 enteric coating Methods 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- -1 bis-nitrophenyl esters Chemical class 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 241000228257 Aspergillus sp. Species 0.000 claims 1
- 241001207508 Cladosporium sp. Species 0.000 claims 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- 241000502261 Endomyces sp. Species 0.000 claims 1
- 241001099841 Eurotium sp. Species 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- 241000603729 Geotrichum sp. Species 0.000 claims 1
- 241000694578 Glomerella sp. (in: Fungi) Species 0.000 claims 1
- 244000068988 Glycine max Species 0.000 claims 1
- 235000010469 Glycine max Nutrition 0.000 claims 1
- 241001346965 Gonatobotryum Species 0.000 claims 1
- 244000017020 Ipomoea batatas Species 0.000 claims 1
- 235000002678 Ipomoea batatas Nutrition 0.000 claims 1
- 241000458385 Moniliella sp. Species 0.000 claims 1
- 240000004713 Pisum sativum Species 0.000 claims 1
- 235000010582 Pisum sativum Nutrition 0.000 claims 1
- 241001158851 Rhodosporidium sp. Species 0.000 claims 1
- 241001030146 Rhodotorula sp. Species 0.000 claims 1
- 241001360381 Saccharomycopsis sp. Species 0.000 claims 1
- 244000061456 Solanum tuberosum Species 0.000 claims 1
- 235000002595 Solanum tuberosum Nutrition 0.000 claims 1
- 241001520881 Sporobolus Species 0.000 claims 1
- 241000641365 Syncephalastrum sp. Species 0.000 claims 1
- 241001079965 Trichosporon sp. Species 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 3
- 238000007385 chemical modification Methods 0.000 abstract description 2
- 230000017854 proteolysis Effects 0.000 abstract description 2
- 238000012239 gene modification Methods 0.000 abstract 1
- 230000005017 genetic modification Effects 0.000 abstract 1
- 235000013617 genetically modified food Nutrition 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 description 21
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 16
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 14
- 108090000317 Chymotrypsin Proteins 0.000 description 7
- 229960002376 chymotrypsin Drugs 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 229940114081 cinnamate Drugs 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 201000011252 Phenylketonuria Diseases 0.000 description 3
- 241000223252 Rhodotorula Species 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010010356 Congenital anomaly Diseases 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- 108010069013 Phenylalanine Hydroxylase Proteins 0.000 description 2
- 102100038223 Phenylalanine-4-hydroxylase Human genes 0.000 description 2
- 241000221523 Rhodotorula toruloides Species 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000008823 permeabilization Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BOEUHAUGJSOEDZ-UHFFFAOYSA-N 2-amino-5,6,7,8-tetrahydro-1h-pteridin-4-one Chemical compound N1CCNC2=C1C(=O)N=C(N)N2 BOEUHAUGJSOEDZ-UHFFFAOYSA-N 0.000 description 1
- 239000000592 Artificial Cell Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000308595 Buckleyzyma aurantiaca Species 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- RGJOEKWQDUBAIZ-IBOSZNHHSA-N CoASH Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-IBOSZNHHSA-N 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 241001149409 Cystobasidium minutum Species 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 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
- 239000004471 Glycine Substances 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 208000028782 Hereditary disease Diseases 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 208000024556 Mendelian disease Diseases 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 241000223253 Rhodotorula glutinis Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000007698 birth defect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- RGJOEKWQDUBAIZ-UHFFFAOYSA-N coenzime A Natural products OC1C(OP(O)(O)=O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-UHFFFAOYSA-N 0.000 description 1
- 239000005516 coenzyme A Substances 0.000 description 1
- 229940093530 coenzyme a Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- KDTSHFARGAKYJN-UHFFFAOYSA-N dephosphocoenzyme A Natural products OC1C(O)C(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCS)OC1N1C2=NC=NC(N)=C2N=C1 KDTSHFARGAKYJN-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 108010064332 quinonoid dihydropterin reductase Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/88—Lyases (4.)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Microbiology (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Medicinal Preparation (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK93755A DK75593D0 (Direct) | 1993-06-25 | 1993-06-25 | |
| PCT/DK1994/000224 WO1995000171A1 (en) | 1993-06-25 | 1994-06-09 | A stabilised phenylalanine ammonia lyase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69429167D1 DE69429167D1 (de) | 2002-01-03 |
| DE69429167T2 true DE69429167T2 (de) | 2002-07-04 |
Family
ID=8097168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69429167T Expired - Lifetime DE69429167T2 (de) | 1993-06-25 | 1994-06-09 | Eine stabilisierte phenylalanin-ammonia-lyase |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5753487A (Direct) |
| EP (1) | EP0703788B1 (Direct) |
| AT (1) | ATE209044T1 (Direct) |
| AU (1) | AU7067594A (Direct) |
| CA (1) | CA2165281A1 (Direct) |
| DE (1) | DE69429167T2 (Direct) |
| DK (2) | DK75593D0 (Direct) |
| ES (1) | ES2168297T3 (Direct) |
| PT (1) | PT703788E (Direct) |
| WO (1) | WO1995000171A1 (Direct) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6051020A (en) | 1994-02-09 | 2000-04-18 | Boston Scientific Technology, Inc. | Bifurcated endoluminal prosthesis |
| EP1552846A3 (en) | 1995-09-29 | 2008-05-07 | BioMarin Pharmaceutical Inc | Use of heparinases to decrease inflammatory responses |
| US5647368A (en) * | 1996-02-28 | 1997-07-15 | Xillix Technologies Corp. | Imaging system for detecting diseased tissue using native fluorsecence in the gastrointestinal and respiratory tract |
| US6190883B1 (en) | 1998-09-09 | 2001-02-20 | Novo Nordisk A/S | Method for the production of heterologous polypeptides in transformed yeast cells |
| US6521748B2 (en) | 1999-08-06 | 2003-02-18 | E. I. Du Pont De Nemours And Company | Polynucleotide encoding a mutant Rhodotorula glutinis tyrosine ammonia lyase polypeptide |
| US6368837B1 (en) | 1999-08-06 | 2002-04-09 | E. I. Du Pont Nemours And Company | Bioproduction of para-hydroxycinnamic acid |
| US20020182201A1 (en) * | 2001-02-16 | 2002-12-05 | Guiyi Zhang-Sun | Matrix stabilized enzyme crystals and methods of use |
| WO2006034373A2 (en) * | 2004-09-17 | 2006-03-30 | Biomarin Pharmaceutical Inc. | Variants and chemically-modified variants of phenylalanine ammonia-lyase |
| US20090038023A1 (en) | 2005-03-10 | 2009-02-05 | Verenium Corporation | Lyase Enzymes, Nucleic Acids Encoding Them and Methods For Making and Using Them |
| US20070122344A1 (en) | 2005-09-02 | 2007-05-31 | University Of Rochester Medical Center Office Of Technology Transfer | Intraoperative determination of nerve location |
| US7531341B1 (en) | 2006-06-12 | 2009-05-12 | Biomarin Pharmaceutical Inc. | Compositions of prokaryotic phenylalanine ammonia-lyase and methods of using compositions thereof |
| US7534595B2 (en) | 2006-06-12 | 2009-05-19 | Biomarin Pharmaceutical Inc. | Compositions of prokaryotic phenylalanine ammonia-lyase and methods of using compositions thereof |
| US20080161744A1 (en) | 2006-09-07 | 2008-07-03 | University Of Rochester Medical Center | Pre-And Intra-Operative Localization of Penile Sentinel Nodes |
| US7537923B2 (en) * | 2007-08-17 | 2009-05-26 | Biomarin Pharmaceutical Inc. | Compositions of prokaryotic phenylalanine ammonia-lyase and methods of treating cancer using compositions thereof |
| US8406860B2 (en) | 2008-01-25 | 2013-03-26 | Novadaq Technologies Inc. | Method for evaluating blush in myocardial tissue |
| US10219742B2 (en) | 2008-04-14 | 2019-03-05 | Novadaq Technologies ULC | Locating and analyzing perforator flaps for plastic and reconstructive surgery |
| EP3372250B1 (en) | 2008-05-02 | 2019-12-25 | Novadaq Technologies ULC | Methods for production and use of substance-loaded erythrocytes for observation and treatment of microvascular hemodynamics |
| US9376659B2 (en) | 2008-07-24 | 2016-06-28 | Arch Personal Care Products, L.P. | Personal care composition containing yeast/polyphenol ferment extract |
| US20110201022A1 (en) * | 2008-07-30 | 2011-08-18 | Biomarin Pharmaceutical Inc. | Assays for detection of phenylalanine ammonia-lyase and antibodies to phenylalanine ammonia-lyase |
| US10492671B2 (en) | 2009-05-08 | 2019-12-03 | Novadaq Technologies ULC | Near infra red fluorescence imaging for visualization of blood vessels during endoscopic harvest |
| CN106834261B (zh) | 2010-02-04 | 2022-02-18 | 生物马林药物股份有限公司 | 原核苯丙氨酸解氨酶变异体的组合物以及利用其组合物的方法 |
| EP2588597A4 (en) | 2010-06-30 | 2013-12-25 | Codexis Inc | CHEMICALLY MODIFIED CARBOHYDRED ANHYDRASES SUITABLE FOR CARBON STORAGE SYSTEMS |
| HK1209995A1 (en) | 2012-06-21 | 2016-04-15 | Novadaq Technologies Inc. | Quantification and analysis of angiography and perfusion |
| EP3521423B1 (en) | 2013-04-18 | 2021-07-21 | Codexis, Inc. | Engineered phenylalanine ammonia lyase polypeptides |
| WO2016049756A1 (en) | 2014-09-29 | 2016-04-07 | Novadaq Technologies Inc. | Imaging a target fluorophore in a biological material in the presence of autofluorescence |
| CA2963450A1 (en) | 2014-10-09 | 2016-04-14 | Novadaq Technologies Inc. | Quantification of absolute blood flow in tissue using fluorescence-mediated photoplethysmography |
| US11140305B2 (en) | 2017-02-10 | 2021-10-05 | Stryker European Operations Limited | Open-field handheld fluorescence imaging systems and methods |
| CA3051262A1 (en) | 2017-02-13 | 2018-08-16 | Codexis, Inc. | Engineered phenylalanine ammonia lyase polypeptides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH453269A4 (Direct) * | 1968-03-29 | 1973-01-31 | ||
| IT1096208B (it) * | 1978-05-12 | 1985-08-26 | Snam Progetti | Composizione adatta alla riduzione del tenore di fenilalanina e metodo impiegante la stessa |
| FR2523445A1 (fr) * | 1982-03-17 | 1983-09-23 | Sanofi Sa | Nouveaux conjugues associant, par liaison covalente, une enzyme et un anticorps, et associations medicamenteuses utilisant lesdits conjugues |
-
1993
- 1993-06-25 DK DK93755A patent/DK75593D0/da not_active Application Discontinuation
-
1994
- 1994-06-09 AU AU70675/94A patent/AU7067594A/en not_active Abandoned
- 1994-06-09 DE DE69429167T patent/DE69429167T2/de not_active Expired - Lifetime
- 1994-06-09 CA CA002165281A patent/CA2165281A1/en not_active Abandoned
- 1994-06-09 US US08/556,963 patent/US5753487A/en not_active Expired - Lifetime
- 1994-06-09 AT AT94919559T patent/ATE209044T1/de not_active IP Right Cessation
- 1994-06-09 DK DK94919559T patent/DK0703788T3/da active
- 1994-06-09 ES ES94919559T patent/ES2168297T3/es not_active Expired - Lifetime
- 1994-06-09 EP EP94919559A patent/EP0703788B1/en not_active Expired - Lifetime
- 1994-06-09 WO PCT/DK1994/000224 patent/WO1995000171A1/en not_active Ceased
- 1994-06-09 PT PT94919559T patent/PT703788E/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7067594A (en) | 1995-01-17 |
| WO1995000171A1 (en) | 1995-01-05 |
| ES2168297T3 (es) | 2002-06-16 |
| EP0703788B1 (en) | 2001-11-21 |
| PT703788E (pt) | 2002-05-31 |
| ATE209044T1 (de) | 2001-12-15 |
| DK0703788T3 (da) | 2002-05-21 |
| DE69429167D1 (de) | 2002-01-03 |
| US5753487A (en) | 1998-05-19 |
| DK75593D0 (Direct) | 1993-06-25 |
| CA2165281A1 (en) | 1995-01-05 |
| EP0703788A1 (en) | 1996-04-03 |
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|---|---|---|---|
| 8364 | No opposition during term of opposition |