SE438509B - Glyceroloxidas och forfarande for dess framstellning samt forfarande for kvantitativ bestemning av glycerol - Google Patents
Glyceroloxidas och forfarande for dess framstellning samt forfarande for kvantitativ bestemning av glycerolInfo
- Publication number
- SE438509B SE438509B SE7804370A SE7804370A SE438509B SE 438509 B SE438509 B SE 438509B SE 7804370 A SE7804370 A SE 7804370A SE 7804370 A SE7804370 A SE 7804370A SE 438509 B SE438509 B SE 438509B
- Authority
- SE
- Sweden
- Prior art keywords
- glycerol
- enzyme
- solution
- nrrl
- oxygen
- Prior art date
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims description 177
- 238000000034 method Methods 0.000 title claims description 48
- 238000002360 preparation method Methods 0.000 title description 6
- 102000004190 Enzymes Human genes 0.000 claims description 88
- 108090000790 Enzymes Proteins 0.000 claims description 88
- 230000000694 effects Effects 0.000 claims description 56
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 49
- 108010090622 glycerol oxidase Proteins 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 241000228212 Aspergillus Species 0.000 claims description 23
- 241000221960 Neurospora Species 0.000 claims description 20
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000002609 medium Substances 0.000 claims description 12
- 244000005700 microbiome Species 0.000 claims description 11
- 239000000049 pigment Substances 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 7
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 5
- 241001480052 Aspergillus japonicus Species 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 241000221961 Neurospora crassa Species 0.000 claims description 4
- 244000070804 Neurospora sitophila Species 0.000 claims description 4
- 235000000376 Neurospora sitophila Nutrition 0.000 claims description 4
- 241000121264 Neurospora tetrasperma Species 0.000 claims description 4
- 235000015097 nutrients Nutrition 0.000 claims description 4
- 241000228197 Aspergillus flavus Species 0.000 claims description 3
- 240000006439 Aspergillus oryzae Species 0.000 claims description 3
- 235000002247 Aspergillus oryzae Nutrition 0.000 claims description 3
- 241000228230 Aspergillus parasiticus Species 0.000 claims description 3
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
- 235000001258 Cinchona calisaya Nutrition 0.000 claims 1
- 101100298295 Drosophila melanogaster flfl gene Proteins 0.000 claims 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 1
- 238000004898 kneading Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 229960000948 quinine Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 50
- 239000007853 buffer solution Substances 0.000 description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 102000016938 Catalase Human genes 0.000 description 12
- 108010053835 Catalase Proteins 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- 102000003992 Peroxidases Human genes 0.000 description 10
- 108040007629 peroxidase activity proteins Proteins 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 8
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 8
- 235000011130 ammonium sulphate Nutrition 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000813 microbial effect Effects 0.000 description 7
- 150000004060 quinone imines Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000002779 inactivation Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- UDZMHVWZLRBHMW-UHFFFAOYSA-N 4-(4-aminophenyl)aniline;periodic acid Chemical compound OI(=O)(=O)=O.C1=CC(N)=CC=C1C1=CC=C(N)C=C1 UDZMHVWZLRBHMW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000385 dialysis solution Substances 0.000 description 3
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 3
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 239000011147 inorganic material Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- -1 sulfhydryl compound Chemical class 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- PPBSJXAHTHPVCC-UHFFFAOYSA-N (1,6-dinitrocyclohexa-2,4-dien-1-yl)hydrazine Chemical compound NNC1([N+]([O-])=O)C=CC=CC1[N+]([O-])=O PPBSJXAHTHPVCC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- 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 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 102000004316 Oxidoreductases Human genes 0.000 description 2
- 108090000854 Oxidoreductases Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004737 colorimetric analysis Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000036284 oxygen consumption Effects 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000005846 sugar alcohols Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000019750 Crude protein Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 102000057621 Glycerol kinases Human genes 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 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 description 1
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 1
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DNSVYPOAUIJAAF-UHFFFAOYSA-N O=CC(O)CO.I(=O)(=O)(=O)O Chemical compound O=CC(O)CO.I(=O)(=O)(=O)O DNSVYPOAUIJAAF-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101710163410 Probable glycerol kinase Proteins 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 102000013009 Pyruvate Kinase Human genes 0.000 description 1
- 108020005115 Pyruvate Kinase Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000251221 Triakidae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 238000005422 blasting Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940116901 diethyldithiocarbamate Drugs 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000002795 fluorescence method Methods 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VQYJLACQFYZHCO-UHFFFAOYSA-N hydron;4-methoxyaniline;chloride Chemical compound [Cl-].COC1=CC=C([NH3+])C=C1 VQYJLACQFYZHCO-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- IYRGXJIJGHOCFS-UHFFFAOYSA-N neocuproine Chemical compound C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 IYRGXJIJGHOCFS-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000003867 organic ammonium compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- YFZOUMNUDGGHIW-UHFFFAOYSA-M p-chloromercuribenzoic acid Chemical compound OC(=O)C1=CC=C([Hg]Cl)C=C1 YFZOUMNUDGGHIW-UHFFFAOYSA-M 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000012128 staining reagent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
-
- 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
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
-
- 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
- Y10S435/817—Enzyme or microbe electrode
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Biomedical Technology (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52044146A JPS6049477B2 (ja) | 1977-04-19 | 1977-04-19 | グリセロ−ル酸化酵素およびその製造法ならびにグリセロ−ル酸化酵素を用いるグリセロ−ルの定量法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7804370L SE7804370L (sv) | 1978-10-20 |
| SE438509B true SE438509B (sv) | 1985-04-22 |
Family
ID=12683485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7804370A SE438509B (sv) | 1977-04-19 | 1978-04-18 | Glyceroloxidas och forfarande for dess framstellning samt forfarande for kvantitativ bestemning av glycerol |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4202941A (no) |
| JP (1) | JPS6049477B2 (no) |
| AU (1) | AU519684B2 (no) |
| CA (1) | CA1124191A (no) |
| CH (1) | CH639421A5 (no) |
| DE (2) | DE2857338C2 (no) |
| DK (1) | DK151266C (no) |
| FR (1) | FR2387992A1 (no) |
| GB (1) | GB1599384A (no) |
| IT (1) | IT1107881B (no) |
| NL (1) | NL189144C (no) |
| NO (1) | NO152975C (no) |
| SE (1) | SE438509B (no) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5850719B2 (ja) * | 1978-10-18 | 1983-11-11 | 協和醗酵工業株式会社 | トリグリセライドの定量方法 |
| US4399218A (en) * | 1980-02-05 | 1983-08-16 | Boehringer Mannheim Gmbh | Method and reagent for the determination of glycerin |
| ATE4328T1 (de) * | 1980-09-19 | 1983-08-15 | Boehringer Mannheim Gmbh | Verfahren und reagens zur bestimmung von glycerin. |
| IT1153913B (it) * | 1982-01-28 | 1987-01-21 | Erba Farmitalia | Metodo e reagenti per l'eliminazione dell'interferenza da bilirubina in alcune determinazioni chimico cliniche |
| DE3210095A1 (de) * | 1982-03-19 | 1983-09-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren und reagenz zur bestimmung von glycerin |
| US5234827A (en) * | 1986-02-04 | 1993-08-10 | Knobbe, Martens, Olson & Bear | Enzymatic process for manufacturing formaldehyde and hydrogen peroxide |
| US4920055A (en) * | 1986-02-04 | 1990-04-24 | American Biogenetics Corporation | Conversion of alcohols to aldehydes and hydrogen peroxide by substrate and product tolerant methanol oxidases |
| US5385827A (en) * | 1989-09-20 | 1995-01-31 | Clark; John R. | Method of geochemical prospecting |
| US6936289B2 (en) | 1995-06-07 | 2005-08-30 | Danisco A/S | Method of improving the properties of a flour dough, a flour dough improving composition and improved food products |
| US6406723B1 (en) | 1997-04-09 | 2002-06-18 | Danisco A/S | Method for preparing flour doughs and products made from such doughs using glycerol oxidase and lipase |
| WO2000005396A1 (en) | 1998-07-21 | 2000-02-03 | Danisco A/S | Foodstuff |
| CN100591212C (zh) | 2001-05-18 | 2010-02-24 | 丹尼斯科有限公司 | 改善生面团和面包质量的方法 |
| US20050196766A1 (en) * | 2003-12-24 | 2005-09-08 | Soe Jorn B. | Proteins |
| US7955814B2 (en) * | 2003-01-17 | 2011-06-07 | Danisco A/S | Method |
| MXPA05007654A (es) | 2003-01-17 | 2005-09-30 | Danisco | Metodo. |
| GB0716126D0 (en) | 2007-08-17 | 2007-09-26 | Danisco | Process |
| US7906307B2 (en) | 2003-12-24 | 2011-03-15 | Danisco A/S | Variant lipid acyltransferases and methods of making |
| US7718408B2 (en) | 2003-12-24 | 2010-05-18 | Danisco A/S | Method |
| GB0405637D0 (en) | 2004-03-12 | 2004-04-21 | Danisco | Protein |
| MX2007000627A (es) | 2004-07-16 | 2007-06-25 | Danisco | Metodo enzimatico de desgomado de aceite. |
| EP2405007B1 (en) * | 2007-01-25 | 2013-12-04 | DuPont Nutrition Biosciences ApS | Production of a lipid acyltransferase from transformed Bacillus licheniformis cells |
-
1977
- 1977-04-19 JP JP52044146A patent/JPS6049477B2/ja not_active Expired
-
1978
- 1978-04-13 GB GB14602/78A patent/GB1599384A/en not_active Expired
- 1978-04-17 CA CA301,236A patent/CA1124191A/en not_active Expired
- 1978-04-18 DK DK168478A patent/DK151266C/da not_active IP Right Cessation
- 1978-04-18 NO NO781363A patent/NO152975C/no unknown
- 1978-04-18 SE SE7804370A patent/SE438509B/sv not_active IP Right Cessation
- 1978-04-18 IT IT7867878A patent/IT1107881B/it active
- 1978-04-18 NL NLAANVRAGE7804133,A patent/NL189144C/xx not_active IP Right Cessation
- 1978-04-19 CH CH420178A patent/CH639421A5/de not_active IP Right Cessation
- 1978-04-19 FR FR7811464A patent/FR2387992A1/fr active Granted
- 1978-04-19 DE DE2857338A patent/DE2857338C2/de not_active Expired
- 1978-04-19 AU AU35254/78A patent/AU519684B2/en not_active Expired
- 1978-04-19 US US05/897,695 patent/US4202941A/en not_active Expired - Lifetime
- 1978-04-19 DE DE2817087A patent/DE2817087C3/de not_active Expired
-
1979
- 1979-11-19 US US06/095,517 patent/US4266023A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2817087C3 (de) | 1985-04-04 |
| DE2857338C2 (de) | 1984-07-12 |
| FR2387992B1 (no) | 1980-10-03 |
| DE2817087B2 (de) | 1980-02-28 |
| NL189144C (nl) | 1993-01-18 |
| NO781363L (no) | 1978-10-20 |
| NL189144B (nl) | 1992-08-17 |
| DK151266B (da) | 1987-11-16 |
| FR2387992A1 (fr) | 1978-11-17 |
| DK151266C (da) | 1988-07-04 |
| CH639421A5 (de) | 1983-11-15 |
| SE7804370L (sv) | 1978-10-20 |
| AU3525478A (en) | 1979-10-25 |
| US4266023A (en) | 1981-05-05 |
| IT1107881B (it) | 1985-12-02 |
| US4202941A (en) | 1980-05-13 |
| IT7867878A0 (it) | 1978-04-18 |
| AU519684B2 (en) | 1981-12-17 |
| DK168478A (da) | 1978-10-20 |
| NO152975B (no) | 1985-09-16 |
| CA1124191A (en) | 1982-05-25 |
| NO152975C (no) | 1985-12-27 |
| GB1599384A (en) | 1981-09-30 |
| NL7804133A (nl) | 1978-10-23 |
| JPS53130488A (en) | 1978-11-14 |
| JPS6049477B2 (ja) | 1985-11-01 |
| DE2817087A1 (de) | 1978-11-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE438509B (sv) | Glyceroloxidas och forfarande for dess framstellning samt forfarande for kvantitativ bestemning av glycerol | |
| Verduyn et al. | Colorimetric alcohol assays with alcohol oxidase | |
| AU614405B2 (en) | Process and agent for the colorimetric determination of an analyte by means of enzymatic oxidation | |
| US4384042A (en) | Method and test composition for determination of hydrogen peroxide | |
| CA1125770A (en) | Reagent and method for the analytic determination of hydrogene peroxide | |
| US4810640A (en) | Method of quantitative assay for 1,5-anhydroglucitol | |
| Verduyn et al. | A simple, sensitive, and accurate alcohol electrode | |
| EP0012446B1 (en) | Acidic uricase, its production and its use for the determination of uric acid | |
| SE445928B (sv) | Odling av aerococcus viridans ifo-12219 eller ifo-12317 och isolering av pyruvatoxidas derur | |
| CA1093993A (en) | Choline oxidase and its production | |
| US4271310A (en) | Method of determining cholinesterase activity and choline derivatives for use in the method | |
| AU707682B2 (en) | Chemiluminescent detection of hydrolytic enzymes using an acridan | |
| US4301244A (en) | Quantitative analysis of free fatty acid and reagent composition therefor | |
| US4677062A (en) | Process for producing bilirubin oxidase | |
| US4255519A (en) | Glycerol oxidase and process for the production thereof | |
| JPS6279780A (ja) | １，５―アンヒドログルシトールの定量法 | |
| Wimalasena et al. | Continuous spectrophotometric assay for ascorbate oxidase based on a novel chromophoric substrate, 2-aminoascorbic acid | |
| Hultmark et al. | Dichloro-p-nitroanisole O-demethylase—A convenient assay for microsomal mixed function oxidase in isolated rat hepatocytes | |
| JPH01265899A (ja) | トリグリセリドの分析用試薬および分析方法 | |
| JPH0272873A (ja) | ヌクレオシドオキシダーゼ及びこれを利用した分析法 | |
| JP3490184B2 (ja) | 新規Ｎ−アルキルグリシンオキシダーゼ、その製造方法、この酵素を用いたＮε−カルボキシメチルリジンの定量用試薬及びその定量方法 | |
| Ikariyama et al. | Delayed luminescence of luminol initiated by a membrane-bound peroxidase | |
| GB2096989A (en) | Choline derivatives and a process for their preparation | |
| JPS5934118B2 (ja) | ダイハイドロキシアセトンの定量法 | |
| JPS6342519B2 (no) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 7804370-0 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 7804370-0 Format of ref document f/p: F |