CA2400014A1 - Preparation of monoglycosidated flavonoids - Google Patents

Preparation of monoglycosidated flavonoids Download PDF

Info

Publication number: CA2400014A1
Authority: CA; Canada
Prior art keywords: solution; enzyme; rutin; reaction; activity
Prior art date: 2000-02-11
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.): Abandoned

Application number

CA002400014A

Other languages

English (en)

French (fr)

Inventor

Hans-Leonhard Ohrem

Achim Schwammle

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Patent GmbH

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

2000-02-11

Filing date

2001-02-09

Publication date

2001-08-16

2001-02-09 Application filed by Individual filed Critical Individual

2001-08-16 Publication of CA2400014A1 publication Critical patent/CA2400014A1/en

Status Abandoned legal-status Critical Current

Links

229930003935 flavonoid Natural products 0.000 title claims abstract description 22
150000002215 flavonoids Chemical class 0.000 title claims abstract description 22
235000017173 flavonoids Nutrition 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title description 4
238000000034 method Methods 0.000 claims abstract description 62
108090000790 Enzymes Proteins 0.000 claims abstract description 60
102000004190 Enzymes Human genes 0.000 claims abstract description 60
230000007071 enzymatic hydrolysis Effects 0.000 claims abstract description 15
238000006047 enzymatic hydrolysis reaction Methods 0.000 claims abstract description 15
238000004519 manufacturing process Methods 0.000 claims abstract description 8
238000006243 chemical reaction Methods 0.000 claims description 56
230000008569 process Effects 0.000 claims description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 41
229960004555 rutoside Drugs 0.000 claims description 40
JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 claims description 39
IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 claims description 38
FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 claims description 38
ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 claims description 38
235000005493 rutin Nutrition 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
OVVGHDNPYGTYIT-ROUHPGRKSA-N alpha-L-Rhap-(1->6)-D-Glcp Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 OVVGHDNPYGTYIT-ROUHPGRKSA-N 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 23
239000000741 silica gel Substances 0.000 claims description 21
229910002027 silica gel Inorganic materials 0.000 claims description 21
108010030923 hesperidinase Proteins 0.000 claims description 17
239000011877 solvent mixture Substances 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims 1
239000000243 solution Substances 0.000 description 63
230000000694 effects Effects 0.000 description 46
IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 41
239000000725 suspension Substances 0.000 description 41
239000000203 mixture Substances 0.000 description 40
239000002245 particle Substances 0.000 description 33
230000005291 magnetic effect Effects 0.000 description 30
OVSQVDMCBVZWGM-IDRAQACASA-N Hirsutrin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)C1=C(c2cc(O)c(O)cc2)Oc2c(c(O)cc(O)c2)C1=O OVSQVDMCBVZWGM-IDRAQACASA-N 0.000 description 26
OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 26
FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 description 25
OVSQVDMCBVZWGM-QCKGUQPXSA-N isoquercetin Natural products OC[C@@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@H](O)[C@@H](O)[C@@H]1O OVSQVDMCBVZWGM-QCKGUQPXSA-N 0.000 description 25
239000007979 citrate buffer Substances 0.000 description 22
239000000047 product Substances 0.000 description 20
SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 19
PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000011521 glass Substances 0.000 description 16
REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 14
239000000872 buffer Substances 0.000 description 14
238000007792 addition Methods 0.000 description 13
108010001078 naringinase Proteins 0.000 description 13
239000000758 substrate Substances 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
229960000587 glutaral Drugs 0.000 description 11
102000004169 proteins and genes Human genes 0.000 description 11
108090000623 proteins and genes Proteins 0.000 description 11
MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 10
239000006249 magnetic particle Substances 0.000 description 10
239000003960 organic solvent Substances 0.000 description 10
-1 rutin Chemical class 0.000 description 10
239000006228 supernatant Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
230000004048 modification Effects 0.000 description 8
238000012986 modification Methods 0.000 description 8
239000011148 porous material Substances 0.000 description 8
235000002639 sodium chloride Nutrition 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
229960002668 sodium chloride Drugs 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 7
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 7
HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 7
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
235000005875 quercetin Nutrition 0.000 description 7
229960001285 quercetin Drugs 0.000 description 7
238000003756 stirring Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229930182470 glycoside Natural products 0.000 description 6
239000000463 material Substances 0.000 description 6
239000008057 potassium phosphate buffer Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000005406 washing Methods 0.000 description 6
101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 5
102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000012065 filter cake Substances 0.000 description 5
150000002338 glycosides Chemical class 0.000 description 5
IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 5
239000000126 substance Substances 0.000 description 5
DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
230000008901 benefit Effects 0.000 description 4
235000014633 carbohydrates Nutrition 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
150000002118 epoxides Chemical group 0.000 description 4
238000000605 extraction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000010445 mica Substances 0.000 description 4
229910052618 mica group Inorganic materials 0.000 description 4
239000000049 pigment Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000007017 scission Effects 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 3
SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 3
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 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
IKGXIBQEEMLURG-UHFFFAOYSA-N Rutin Chemical compound OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000003172 aldehyde group Chemical group 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000011942 biocatalyst Substances 0.000 description 3
239000007853 buffer solution Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000001514 detection method Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000975 dye Substances 0.000 description 3
229930003944 flavone Natural products 0.000 description 3
235000011949 flavones Nutrition 0.000 description 3
239000008103 glucose Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000002955 isolation Methods 0.000 description 3
235000008777 kaempferol Nutrition 0.000 description 3
238000002156 mixing Methods 0.000 description 3
UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 3
239000002994 raw material Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
108090000604 Hydrolases Proteins 0.000 description 2
102000004157 Hydrolases Human genes 0.000 description 2
UIDGLYUNOUKLBM-BPTRYNHESA-N Isorhamnetin rutinoside Chemical compound COc1cc(ccc1O)-c1oc2cc(O)cc(O)c2c(=O)c1O[C@@H]1OC(CO[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O UIDGLYUNOUKLBM-BPTRYNHESA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000036425 denaturation Effects 0.000 description 2
238000004925 denaturation Methods 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
150000002212 flavone derivatives Chemical class 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000004907 flux Effects 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
229910052809 inorganic oxide Inorganic materials 0.000 description 2
150000002772 monosaccharides Chemical class 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
238000012856 packing Methods 0.000 description 2
239000008363 phosphate buffer Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
238000012289 standard assay Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 2
GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000873224 Capparaceae Species 0.000 description 1
235000017336 Capparis spinosa Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000272165 Charadriidae Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000207199 Citrus Species 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 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 description 1
241000220485 Fabaceae Species 0.000 description 1
240000008620 Fagopyrum esculentum Species 0.000 description 1
235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
241000555682 Forsythia x intermedia Species 0.000 description 1
108010056771 Glucosidases Proteins 0.000 description 1
102000004366 Glucosidases Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
235000017309 Hypericum perforatum Nutrition 0.000 description 1
244000141009 Hypericum perforatum Species 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
GQODBWLKUWYOFX-UHFFFAOYSA-N Isorhamnetin Natural products C1=C(O)C(C)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 GQODBWLKUWYOFX-UHFFFAOYSA-N 0.000 description 1
241001533590 Junonia Species 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
WVVOBOZHTQJXPB-UHFFFAOYSA-N N-anilino-N-nitronitramide Chemical compound [N+](=O)([O-])N(NC1=CC=CC=C1)[N+](=O)[O-] WVVOBOZHTQJXPB-UHFFFAOYSA-N 0.000 description 1
241000208125 Nicotiana Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
108010073038 Penicillin Amidase Proteins 0.000 description 1
241000985535 Penicillium decumbens Species 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
101710196640 Protein 3.8 Proteins 0.000 description 1
OVVGHDNPYGTYIT-VHBGUFLRSA-N Robinobiose Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](C)O1 OVVGHDNPYGTYIT-VHBGUFLRSA-N 0.000 description 1
240000005746 Ruta graveolens Species 0.000 description 1
235000001347 Ruta graveolens Nutrition 0.000 description 1
102000007562 Serum Albumin Human genes 0.000 description 1
108010071390 Serum Albumin Proteins 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
235000002634 Solanum Nutrition 0.000 description 1
241000207763 Solanum Species 0.000 description 1
244000046101 Sophora japonica Species 0.000 description 1
235000010586 Sophora japonica Nutrition 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
240000006909 Tilia x europaea Species 0.000 description 1
241000894434 Turbo cornutus Species 0.000 description 1
235000004031 Viola x wittrockiana Nutrition 0.000 description 1
229930003268 Vitamin C Natural products 0.000 description 1
108700040099 Xylose isomerases Proteins 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
PNNNRSAQSRJVSB-KVTDHHQDSA-N aldehydo-D-rhamnose Chemical group C[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O PNNNRSAQSRJVSB-KVTDHHQDSA-N 0.000 description 1
PNNNRSAQSRJVSB-BXKVDMCESA-N aldehydo-L-rhamnose Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O PNNNRSAQSRJVSB-BXKVDMCESA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
235000015278 beef Nutrition 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036983 biotransformation Effects 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Chemical class 0.000 description 1
235000010338 boric acid Nutrition 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
235000019628 coolness Nutrition 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000012937 correction Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000002213 flavones Chemical class 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
229930182478 glucoside Natural products 0.000 description 1
125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000007689 inspection Methods 0.000 description 1
SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
235000008800 isorhamnetin Nutrition 0.000 description 1
235000021374 legumes Nutrition 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
238000007885 magnetic separation Methods 0.000 description 1
230000005415 magnetization Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
238000001728 nano-filtration Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
238000005325 percolation Methods 0.000 description 1
230000002572 peristaltic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000012716 precipitator Substances 0.000 description 1
238000011045 prefiltration Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000012460 protein solution Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000003908 quality control method Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000003134 recirculating effect Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
239000001229 ruta graveolens Substances 0.000 description 1
OVVGHDNPYGTYIT-BNXXONSGSA-N rutinose Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 OVVGHDNPYGTYIT-BNXXONSGSA-N 0.000 description 1
238000001612 separation test Methods 0.000 description 1
238000002444 silanisation Methods 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000032258 transport Effects 0.000 description 1
BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)

CA002400014A 2000-02-11 2001-02-09 Preparation of monoglycosidated flavonoids Abandoned CA2400014A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE10006147A DE10006147A1 (de)	2000-02-11	2000-02-11	Verfahren zur Herstellung von monoglycosidierten Flavonoiden
DE10006147.8		2000-02-11
PCT/EP2001/001447 WO2001059143A1 (de)	2000-02-11	2001-02-09	Verfahren zur herstellung von monoglycosidierten flavonoiden

Publications (1)

Publication Number	Publication Date
CA2400014A1 true CA2400014A1 (en)	2001-08-16

Family

ID=7630616

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002400014A Abandoned CA2400014A1 (en)	2000-02-11	2001-02-09	Preparation of monoglycosidated flavonoids

Country Status (9)

Country	Link
EP (1)	EP1259632A1 (de)
JP (1)	JP2003522532A (de)
KR (1)	KR20030013371A (de)
CN (1)	CN1416470A (de)
AU (1)	AU2001231726A1 (de)
BR (1)	BR0108273A (de)
CA (1)	CA2400014A1 (de)
DE (1)	DE10006147A1 (de)
WO (1)	WO2001059143A1 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2496316A1 (en) *	2002-09-23	2004-04-01	Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture	Extraction, purification and conversion of flavonoids from plant biomass
CN101100683B (zh) *	2006-09-08	2010-05-12	颜廷和	一种甙元型黄酮生物转化及纯化的方法
KR20080033705A (ko) *	2006-10-13	2008-04-17	(주)아모레퍼시픽	캄페롤-3-ｏ-루티노사이드의 제조방법
JP5184786B2 (ja) *	2007-01-19	2013-04-17	サントリーホールディングス株式会社	フラボノイド類の配糖化方法
KR101105846B1 (ko) *	2009-08-17	2012-01-13	주식회사 젬백스앤카엘	흡착제 교체가 용이한 필터 여재
CN101670010B (zh) *	2009-10-10	2012-06-20	杭州富春食品添加剂有限公司	一种黄酮苷类物质的提取方法
CN102286576B (zh) *	2011-09-14	2013-11-06	江苏科技大学	强化酶法合成异槲皮苷的介质工程方法
CN105779473A (zh) *	2014-12-19	2016-07-20	上海交通大学	鼠李糖异黄酮的合成基因簇及其应用
KR102528136B1 (ko) *	2018-01-02	2023-05-02	최병국	이소케르세틴 및 알파-글리코실이소케르세틴의 제조방법
KR102615753B1 (ko) *	2022-11-30	2023-12-19	주식회사 다인소재	항균성 및 항산화 활성이 우수한 이소케르세틴의 제조방법

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8727223D0 (en) *	1987-11-20	1987-12-23	Unilever Plc	Preparing l-rhamnose
US4971812A (en) *	1989-08-31	1990-11-20	National Science Council	Immobilized penicillium sp. naringnase and its use in removing naringin and limonin from fruit juice
EP0599159B1 (de) *	1992-11-27	2001-09-19	Aventis Research & Technologies GmbH & Co. KG	Heterogenes Proteingemisch mit alpha-L-rhamnosidase Aktivität, Verfahren zu ihrer Herstellung und ihre Verwendung.

2000
- 2000-02-11 DE DE10006147A patent/DE10006147A1/de not_active Withdrawn
2001
- 2001-02-09 CA CA002400014A patent/CA2400014A1/en not_active Abandoned
- 2001-02-09 KR KR1020027010449A patent/KR20030013371A/ko active IP Right Grant
- 2001-02-09 BR BR0108273-6A patent/BR0108273A/pt not_active IP Right Cessation
- 2001-02-09 WO PCT/EP2001/001447 patent/WO2001059143A1/de not_active Application Discontinuation
- 2001-02-09 AU AU2001231726A patent/AU2001231726A1/en not_active Abandoned
- 2001-02-09 JP JP2001558479A patent/JP2003522532A/ja active Pending
- 2001-02-09 CN CN01806409A patent/CN1416470A/zh active Pending
- 2001-02-09 EP EP01903733A patent/EP1259632A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
KR20030013371A (ko)	2003-02-14
WO2001059143A1 (de)	2001-08-16
DE10006147A1 (de)	2001-08-16
CN1416470A (zh)	2003-05-07
AU2001231726A1 (en)	2001-08-20
BR0108273A (pt)	2003-03-05
JP2003522532A (ja)	2003-07-29
EP1259632A1 (de)	2002-11-27

Publication	Publication Date	Title
Shin et al.	1998	Continuous production of galacto-oligosaccharides from lactose by Bullera singularis β-galactosidase immobilized in chitosan beads
Ribeiro	2011	Naringinases: occurrence, characteristics, and applications
Wang et al.	2013	Enzymatic production of lactulose and 1-lactulose: current state and perspectives
CA2400014A1 (en)	2001-08-16	Preparation of monoglycosidated flavonoids
Díaz et al.	2006	Towards the development of a membrane reactor for enzymatic inulin hydrolysis
Martins et al.	2018	Exploring magnetic and imprinted cross-linked enzyme aggregates of rhamnopyranosidase in microbioreactors
EP0670890B1 (de)	1997-05-28	Bioreaktor mit immobilisierten milchsäurebakterien und seine verwendung
CN101532039A (zh)	2009-09-16	磁性纳米固定化酶催化生产大豆异黄酮苷元的方法
Belleville et al.	2001	Preparation of hybrid membranes for enzymatic reaction
US20030157653A1 (en)	2003-08-21	Method for producing monoglycosidated flavonoids
JPS61249396A (ja)	1986-11-06	イソマルツロ−スの酵素による連続式製造法
Kmínková et al.	1983	Comparison of pectolytic enzymes covalently bound to synthetic ion exchangers using different methods of binding
US6420142B1 (en)	2002-07-16	Method for enzymatic splitting of rutinosides
Mateescu et al.	1989	Ready to use p-Benzoquinone activated supports for biochemical coupling, with special applications for laccase immobilization
Lu et al.	2017	Recent progress on galactooligosaccharides synthesis by microbial β-galactosidase
CN105732663A (zh)	2016-07-06	6-氨基青霉烷酸的制备方法
CN103525893A (zh)	2014-01-22	一种头孢菌素酰化酶催化制备7-氨基头孢烷酸的方法
Garcia-Gonzalez et al.	2023	Continuous production of honey oligosaccharides in packed-bed reactors with immobilized α-glucosidase from Metschnikowia reukaufii
EP0138338B1 (de)	1987-09-16	Penicillinamidase
CN112501153A (zh)	2021-03-16	一种固定化纤维二糖差向异构酶及其应用于乳果糖制备的方法
CN111607584A (zh)	2020-09-01	一种树脂固定化海洋环糊精葡萄糖基转移酶的方法
Samejima et al.	1978	Production of 5’-Mononucleotides Using Immobilized 5’-Phosphodiesterase and 5’-AMP Deaminase
KR20200081038A (ko)	2020-07-07	재조합 CGTase 효소 고정화 기술을 이용한 ascorbic acid-2-glucoside (AA-2G) 제조방법
JPS5854799B2 (ja)	1983-12-06	グリコシルビタミンの製造方法
CN110846306B (zh)	2021-08-17	一种双亲性酶固定化载体

Legal Events

Date	Code	Title	Description
2002-08-08	EEER	Examination request
2005-02-09	FZDE	Dead