CA1300061C - Process for preparing cyclooctaamylose - Google Patents
Process for preparing cyclooctaamyloseInfo
- Publication number
- CA1300061C CA1300061C CA000565420A CA565420A CA1300061C CA 1300061 C CA1300061 C CA 1300061C CA 000565420 A CA000565420 A CA 000565420A CA 565420 A CA565420 A CA 565420A CA 1300061 C CA1300061 C CA 1300061C
- Authority
- CA
- Canada
- Prior art keywords
- cyclooctaamylose
- starch
- process according
- range
- employed
- 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
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 229920002472 Starch Polymers 0.000 claims abstract description 28
- 235000019698 starch Nutrition 0.000 claims abstract description 28
- 239000008107 starch Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000008139 complexing agent Substances 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 7
- 125000004429 atom Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical group [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims abstract description 3
- 108090000790 Enzymes Proteins 0.000 claims description 10
- 102000004190 Enzymes Human genes 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 230000007017 scission Effects 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- -1 methoxy, ethoxy Chemical group 0.000 description 5
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 4
- 241000178960 Paenibacillus macerans Species 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- GJJSUPSPZIZYPM-UHFFFAOYSA-N 1,4-dioxacyclohexadecane-5,16-dione Chemical compound O=C1CCCCCCCCCCC(=O)OCCO1 GJJSUPSPZIZYPM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZGEHHVDYDNXYMW-UHFFFAOYSA-N cyclohexadec-8-en-1-one Chemical compound O=C1CCCCCCCC=CCCCCCC1 ZGEHHVDYDNXYMW-UHFFFAOYSA-N 0.000 description 3
- CDJMUDSSRKZTDJ-UHFFFAOYSA-N cyclotetradec-7-en-1-one Chemical compound O=C1CCCCCCC=CCCCCC1 CDJMUDSSRKZTDJ-UHFFFAOYSA-N 0.000 description 3
- VHUGWUBIUBBUAF-UHFFFAOYSA-N cyclotridecanone Chemical compound O=C1CCCCCCCCCCCC1 VHUGWUBIUBBUAF-UHFFFAOYSA-N 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- MKEIDVFLAWJKMY-UHFFFAOYSA-N 1,7-dioxacycloheptadecan-8-one Chemical compound O=C1CCCCCCCCCOCCCCCO1 MKEIDVFLAWJKMY-UHFFFAOYSA-N 0.000 description 2
- FXKHTSOJWNCNRI-UHFFFAOYSA-N 15-oxabicyclo[12.1.0]pentadec-7-ene Chemical compound C1CCCCC=CCCCCCC2OC21 FXKHTSOJWNCNRI-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- WHGYBXFWUBPSRW-UHFFFAOYSA-N Cycloheptaamylose Natural products O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO WHGYBXFWUBPSRW-UHFFFAOYSA-N 0.000 description 2
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 2
- 108010073178 Glucan 1,4-alpha-Glucosidase Proteins 0.000 description 2
- 102100022624 Glucoamylase Human genes 0.000 description 2
- 229930092411 Swietenocoumarin D Natural products 0.000 description 2
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- ZKVZSBSZTMPBQR-UHFFFAOYSA-N cycloheptadec-9-en-1-one Chemical compound O=C1CCCCCCCC=CCCCCCCC1 ZKVZSBSZTMPBQR-UHFFFAOYSA-N 0.000 description 2
- JNFIMRWCDIOUMT-UHFFFAOYSA-N cyclooctadecane Chemical compound C1CCCCCCCCCCCCCCCCC1 JNFIMRWCDIOUMT-UHFFFAOYSA-N 0.000 description 2
- LKFRMGXDPLMLIF-UHFFFAOYSA-N cyclotetracosane-1,8,16-trione Chemical compound O=C1CCCCCCCCC(=O)CCCCCCC(=O)CCCCCCC1 LKFRMGXDPLMLIF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000001807 (9E)-cycloheptadec-9-en-1-one Substances 0.000 description 1
- MEKAMLHVYKHQBV-UHFFFAOYSA-N 1,4-dioxacycloicosane-5,20-dione Chemical compound O=C1CCCCCCCCCCCCCCC(=O)OCCO1 MEKAMLHVYKHQBV-UHFFFAOYSA-N 0.000 description 1
- RFQCCPKKTMJJET-UHFFFAOYSA-N 1,4-dioxaspiro[4.15]icosane Chemical compound O1CCOC11CCCCCCCCCCCCCCC1 RFQCCPKKTMJJET-UHFFFAOYSA-N 0.000 description 1
- KTOHRMAEFBZKTE-UHFFFAOYSA-N 1,5,9,13-tetramethylcyclohexadeca-1,5,9,13-tetraene Chemical compound CC1=CCCC(C)=CCCC(C)=CCCC(C)=CCC1 KTOHRMAEFBZKTE-UHFFFAOYSA-N 0.000 description 1
- MRMOPGVGWFNHIN-UHFFFAOYSA-N 1,6-dioxacycloheptadecan-7-one Chemical compound O=C1CCCCCCCCCCOCCCCO1 MRMOPGVGWFNHIN-UHFFFAOYSA-N 0.000 description 1
- RDKBAHCRKQTADL-UHFFFAOYSA-N 1,7-diazacyclohexadecane-8,16-dione Chemical compound O=C1CCCCCCCC(=O)NCCCCCN1 RDKBAHCRKQTADL-UHFFFAOYSA-N 0.000 description 1
- ITWWEYPYLJIKTB-UHFFFAOYSA-N 1-azacyclotetradec-9-en-2-one Chemical compound O=C1CCCCCCC=CCCCCN1 ITWWEYPYLJIKTB-UHFFFAOYSA-N 0.000 description 1
- KFHHBWJZXNKNGE-UHFFFAOYSA-N 1-oxacycloheptadec-12-en-2-one Chemical compound O=C1CCCCCCCCCC=CCCCCO1 KFHHBWJZXNKNGE-UHFFFAOYSA-N 0.000 description 1
- ALVVVGFCZNOOFD-UHFFFAOYSA-N 13-hydroxyimino-oxacyclohexadecan-2-one Chemical compound ON=C1CCCCCCCCCCC(=O)OCCC1 ALVVVGFCZNOOFD-UHFFFAOYSA-N 0.000 description 1
- LOKPJYNMYCVCRM-UHFFFAOYSA-N 16-Hexadecanolide Chemical compound O=C1CCCCCCCCCCCCCCCO1 LOKPJYNMYCVCRM-UHFFFAOYSA-N 0.000 description 1
- ZCAWTINMLHVGOY-UHFFFAOYSA-N 17-oxabicyclo[14.1.0]heptadeca-4,8,12-triene Chemical compound C1CC=CCCC=CCCC=CCCC2OC21 ZCAWTINMLHVGOY-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
- RCOKMWAKYZDWAA-UHFFFAOYSA-N 2-methyl-1,4-dioxacyclohexadecane-5,16-dione Chemical compound CC1COC(=O)CCCCCCCCCCC(=O)O1 RCOKMWAKYZDWAA-UHFFFAOYSA-N 0.000 description 1
- ASQBFCPNMMCIGN-UHFFFAOYSA-N 2-methylcyclotridecan-1-one Chemical compound CC1CCCCCCCCCCCC1=O ASQBFCPNMMCIGN-UHFFFAOYSA-N 0.000 description 1
- DWDUMNPMUZVGRS-UHFFFAOYSA-N 8,9-dimethoxycyclohexadecene Chemical compound COC1CCCCCCCC=CCCCCCC1OC DWDUMNPMUZVGRS-UHFFFAOYSA-N 0.000 description 1
- OVMFRYKLEUFMRG-UHFFFAOYSA-N 9-methoxycyclohexadecene Chemical compound COC1CCCCCCCC=CCCCCCC1 OVMFRYKLEUFMRG-UHFFFAOYSA-N 0.000 description 1
- 241000193752 Bacillus circulans Species 0.000 description 1
- 241000194107 Bacillus megaterium Species 0.000 description 1
- 241000193407 Bacillus ohbensis Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002245 Dextrose equivalent Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000191953 Kocuria varians Species 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- ALHUZKCOMYUFRB-OAHLLOKOSA-N Muscone Chemical compound C[C@@H]1CCCCCCCCCCCCC(=O)C1 ALHUZKCOMYUFRB-OAHLLOKOSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SUAZRRTWDATHDK-UHFFFAOYSA-N cycloheptadecane Chemical compound C1CCCCCCCCCCCCCCCC1 SUAZRRTWDATHDK-UHFFFAOYSA-N 0.000 description 1
- FXRYNTPSWKKHOY-UHFFFAOYSA-N cyclohexadec-8-en-1-yl acetate Chemical compound CC(=O)OC1CCCCCCCC=CCCCCCC1 FXRYNTPSWKKHOY-UHFFFAOYSA-N 0.000 description 1
- ZBIUKDQKGBKABI-UHFFFAOYSA-N cyclohexadec-8-yn-1-one Chemical compound O=C1CCCCCCCC#CCCCCCC1 ZBIUKDQKGBKABI-UHFFFAOYSA-N 0.000 description 1
- SFWOYLWPQYGZHK-UHFFFAOYSA-N cyclohexadeca-4,8,12-trien-1-ol Chemical compound OC1CCCC=CCCC=CCCC=CCC1 SFWOYLWPQYGZHK-UHFFFAOYSA-N 0.000 description 1
- IBHQQFOERGXDMC-UHFFFAOYSA-N cyclohexadecane-1,8-diol Chemical compound OC1CCCCCCCCC(O)CCCCCC1 IBHQQFOERGXDMC-UHFFFAOYSA-N 0.000 description 1
- SSRUWICMOKOXLR-UHFFFAOYSA-N cyclohexadecane-1,8-dione Chemical compound O=C1CCCCCCCCC(=O)CCCCCC1 SSRUWICMOKOXLR-UHFFFAOYSA-N 0.000 description 1
- VSQURHGSZWBWFZ-UHFFFAOYSA-N cyclohexadecane-1,9-dione Chemical compound O=C1CCCCCCCC(=O)CCCCCCC1 VSQURHGSZWBWFZ-UHFFFAOYSA-N 0.000 description 1
- KUZFTOAYXWRQAA-UHFFFAOYSA-N cyclopentadec-8-en-1-one Chemical compound O=C1CCCCCCC=CCCCCCC1 KUZFTOAYXWRQAA-UHFFFAOYSA-N 0.000 description 1
- AQLCQUACLXRPKV-UHFFFAOYSA-N cyclopentadeca-1,8-diene Chemical compound C1CCCC=CCCCCCC=CCC1 AQLCQUACLXRPKV-UHFFFAOYSA-N 0.000 description 1
- CRTZBFYNHOIRRM-UHFFFAOYSA-N cyclopentadecane-1,8-dione Chemical compound O=C1CCCCCCCC(=O)CCCCCC1 CRTZBFYNHOIRRM-UHFFFAOYSA-N 0.000 description 1
- VPBPFAIWNCCMAY-UHFFFAOYSA-N cyclotetracosa-1,9,17-triene Chemical compound C1CCCC=CCCCCCCC=CCCCCCCC=CCC1 VPBPFAIWNCCMAY-UHFFFAOYSA-N 0.000 description 1
- HJOXXAJXPKIPQX-UHFFFAOYSA-N cyclotetradec-7-en-1-ol Chemical compound OC1CCCCCCC=CCCCCC1 HJOXXAJXPKIPQX-UHFFFAOYSA-N 0.000 description 1
- WCMISCDQOHKOAN-UHFFFAOYSA-N cyclotetradeca-1,8-diene Chemical compound C1CCC=CCCCCCC=CCC1 WCMISCDQOHKOAN-UHFFFAOYSA-N 0.000 description 1
- MXTFEOYSFWGYJD-UHFFFAOYSA-N cyclotetradecane-1,2-dione Chemical compound O=C1CCCCCCCCCCCCC1=O MXTFEOYSFWGYJD-UHFFFAOYSA-N 0.000 description 1
- SFZJEGHAKFMLOC-UHFFFAOYSA-N cyclotetradecane-1,8-dione Chemical compound O=C1CCCCCCC(=O)CCCCCC1 SFZJEGHAKFMLOC-UHFFFAOYSA-N 0.000 description 1
- FUGDHQXYVPQGLJ-UHFFFAOYSA-N cyclotetradecanone Chemical compound O=C1CCCCCCCCCCCCC1 FUGDHQXYVPQGLJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BZWBSKRKVASNDF-UHFFFAOYSA-N heptadec-8-ene Chemical compound [CH2]CCCCCCC=CCCCCCCCC BZWBSKRKVASNDF-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- LFSYLMRHJKGLDV-UHFFFAOYSA-N oxacyclopentadecan-2-one Chemical compound O=C1CCCCCCCCCCCCCO1 LFSYLMRHJKGLDV-UHFFFAOYSA-N 0.000 description 1
- 150000002966 pentacyclic triterpenoids Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003521 tetracyclic triterpenoids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- 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
- C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873716181 DE3716181A1 (de) | 1987-05-14 | 1987-05-14 | Verfahren zur herstellung von cyclooctaamylose |
| DEP3716181.4 | 1987-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1300061C true CA1300061C (en) | 1992-05-05 |
Family
ID=6327568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000565420A Expired - Lifetime CA1300061C (en) | 1987-05-14 | 1988-04-28 | Process for preparing cyclooctaamylose |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4822874A (2) |
| EP (1) | EP0291067B1 (2) |
| JP (1) | JPS63287495A (2) |
| AT (1) | ATE111108T1 (2) |
| CA (1) | CA1300061C (2) |
| DE (2) | DE3716181A1 (2) |
| DK (1) | DK264388A (2) |
| HU (1) | HU203772B (2) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4009822A1 (de) * | 1990-03-27 | 1991-10-02 | Consortium Elektrochem Ind | (gamma)-cgtase |
| CN1072185A (zh) * | 1991-11-13 | 1993-05-19 | 美国玉米产品公司 | 制备非混浊型环糊精的方法 |
| JP3360291B2 (ja) * | 1993-02-09 | 2002-12-24 | 天野エンザイム株式会社 | γ−サイクロデキストリンの増収方法 |
| TW383336B (en) * | 1993-06-24 | 2000-03-01 | Consortium Elektrochem Ind | Cyclodextrin glycosyl transferases for the preparation of gama-cyclodextrin |
| US5550222A (en) * | 1994-12-14 | 1996-08-27 | American Maize-Products Company | Process for producing gamma-cyclodextrin |
| DE19615336A1 (de) * | 1996-04-18 | 1997-10-23 | Consortium Elektrochem Ind | Cyclodextringlycosyltransferasen zur Produktion von gamma-Cyclodextrin |
| US6472192B1 (en) | 1996-04-18 | 2002-10-29 | Consortium für elektrochemische Industrie GmbH | Cyclodextrin glycosyl transferases for producing γ-cyclodextrin |
| US5726328A (en) * | 1996-07-09 | 1998-03-10 | V. Mane Fils S.A. | Preparation of cis-isoambrettolides and their use as a fragrance |
| US7709230B2 (en) | 2001-04-27 | 2010-05-04 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Process for producing isomaltose and uses thereof |
| US7846886B2 (en) | 2006-02-07 | 2010-12-07 | Symrise Gmbh & Co. Kg | Mixtures of unsaturated macrocyclic epoxides as odoriferous substances |
| MX2008002145A (es) * | 2007-02-22 | 2009-02-25 | Rohm & Haas | Metodo para elaborar un complejo. |
| US9764580B2 (en) | 2013-03-29 | 2017-09-19 | Dai Nippon Printing Co., Ltd. | Thermal transfer sheet, coating liquid for colorant layer, method for manufacturing thermal transfer sheet, and image forming method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3318732A (en) * | 1963-08-08 | 1967-05-09 | Nat Starch Chem Corp | Method for the fractionation of starch |
| HU194939B (en) * | 1983-12-22 | 1988-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing alpha- beta- and gamma cyclodextrine of high yield capacity |
| JPH0626667B2 (ja) * | 1985-10-31 | 1994-04-13 | メルシャン株式会社 | サイクロデキストリン吸着材及びその用途 |
-
1987
- 1987-05-14 DE DE19873716181 patent/DE3716181A1/de not_active Withdrawn
-
1988
- 1988-04-19 US US07/183,661 patent/US4822874A/en not_active Expired - Lifetime
- 1988-04-28 CA CA000565420A patent/CA1300061C/en not_active Expired - Lifetime
- 1988-05-12 JP JP63113708A patent/JPS63287495A/ja active Granted
- 1988-05-13 AT AT88107694T patent/ATE111108T1/de not_active IP Right Cessation
- 1988-05-13 EP EP88107694A patent/EP0291067B1/de not_active Expired - Lifetime
- 1988-05-13 HU HU882399A patent/HU203772B/hu unknown
- 1988-05-13 DE DE3851362T patent/DE3851362D1/de not_active Expired - Lifetime
- 1988-05-13 DK DK264388A patent/DK264388A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0291067B1 (de) | 1994-09-07 |
| HUT46936A (en) | 1988-12-28 |
| DE3716181A1 (de) | 1988-12-08 |
| US4822874A (en) | 1989-04-18 |
| EP0291067A3 (en) | 1989-07-19 |
| ATE111108T1 (de) | 1994-09-15 |
| JPH0544279B2 (2) | 1993-07-05 |
| HU203772B (en) | 1991-09-30 |
| DE3851362D1 (de) | 1994-10-13 |
| DK264388D0 (da) | 1988-05-13 |
| EP0291067A2 (de) | 1988-11-17 |
| DK264388A (da) | 1988-11-15 |
| JPS63287495A (ja) | 1988-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20090505 |