JPS62293A - Ｌ−ラムノ−スの製造法 - Google Patents
Ｌ−ラムノ−スの製造法Info
- Publication number
- JPS62293A JPS62293A JP13969485A JP13969485A JPS62293A JP S62293 A JPS62293 A JP S62293A JP 13969485 A JP13969485 A JP 13969485A JP 13969485 A JP13969485 A JP 13969485A JP S62293 A JPS62293 A JP S62293A
- Authority
- JP
- Japan
- Prior art keywords
- rhamnose
- flavonoid
- enzyme
- solution
- purity
- 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.)
- Granted
Links
- 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 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims abstract description 31
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 108090000790 Enzymes Proteins 0.000 claims abstract description 17
- 102000004190 Enzymes Human genes 0.000 claims abstract description 17
- -1 flavonoid compound Chemical class 0.000 claims abstract description 14
- 229930003935 flavonoid Natural products 0.000 claims abstract description 13
- 235000017173 flavonoids Nutrition 0.000 claims abstract description 13
- 229930182486 flavonoid glycoside Natural products 0.000 claims abstract description 12
- 150000007955 flavonoid glycosides Chemical class 0.000 claims abstract description 12
- 238000005377 adsorption chromatography Methods 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 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 abstract description 7
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 abstract description 3
- 229930019673 naringin Natural products 0.000 abstract description 3
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 abstract description 3
- 229940052490 naringin Drugs 0.000 abstract description 3
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 abstract description 2
- 241000228245 Aspergillus niger Species 0.000 abstract description 2
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 abstract description 2
- 241001540751 Talaromyces ruber Species 0.000 abstract description 2
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 abstract description 2
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 abstract description 2
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 abstract description 2
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 abstract description 2
- 229940025878 hesperidin Drugs 0.000 abstract description 2
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BNRKZHXOBMEUGK-NRBMBCGPSA-N (2r,3r,4r,5r,6s)-6-methyloxane-2,3,4,5-tetrol;hydrate Chemical compound O.C[C@@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@H]1O BNRKZHXOBMEUGK-NRBMBCGPSA-N 0.000 description 3
- 241000228212 Aspergillus Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000228143 Penicillium Species 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 108010001078 naringinase Proteins 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YFVGIJBUXMQFOF-PJOVQGMDSA-N 5-hydroxy-2-(4-methoxyphenyl)-7-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one Chemical compound C1=CC(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)O1 YFVGIJBUXMQFOF-PJOVQGMDSA-N 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- YFVGIJBUXMQFOF-SAXLCNSLSA-N Linarin Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@H](Oc2cc(O)c3C(=O)C=C(c4ccc(OC)cc4)Oc3c2)O1)[C@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 YFVGIJBUXMQFOF-SAXLCNSLSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- ADSYMQORONDIDD-ZJHVPRRPSA-N hesperetin 7-O-beta-D-glucoside Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)=CC(O)=C2C(=O)C1 ADSYMQORONDIDD-ZJHVPRRPSA-N 0.000 description 1
- 108010030923 hesperidinase Proteins 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000008265 rhamnosides Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13969485A JPS62293A (ja) | 1985-06-26 | 1985-06-26 | Ｌ−ラムノ−スの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13969485A JPS62293A (ja) | 1985-06-26 | 1985-06-26 | Ｌ−ラムノ−スの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62293A true JPS62293A (ja) | 1987-01-06 |
| JPH053280B2 JPH053280B2 (enrdf_load_stackoverflow) | 1993-01-14 |
Family
ID=15251239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13969485A Granted JPS62293A (ja) | 1985-06-26 | 1985-06-26 | Ｌ−ラムノ−スの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62293A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0599159A2 (de) | 1992-11-27 | 1994-06-01 | Hoechst Aktiengesellschaft | a-L-Rhamnosidase zur Gewinnung von Rhamnose, ein Verfahren zur Herstellung und ihre Verwendung |
| US5501966A (en) * | 1992-06-25 | 1996-03-26 | Hoechst Aktiengesellschaft | Pseudomonas aeruginosa and its use in a process for the biotechnological preparation of L-rhamnose |
| WO2000026400A1 (de) * | 1998-10-30 | 2000-05-11 | Merck Patent Gmbh | Verfahren zur enzymatischen spaltung von rutinosiden |
-
1985
- 1985-06-26 JP JP13969485A patent/JPS62293A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5501966A (en) * | 1992-06-25 | 1996-03-26 | Hoechst Aktiengesellschaft | Pseudomonas aeruginosa and its use in a process for the biotechnological preparation of L-rhamnose |
| US5658793A (en) * | 1992-06-25 | 1997-08-19 | Hoechst Aktiengesellschaft | Pseudomonas aeruginosa and its use in a process for the biotechnological preparation of L-rhamnose |
| EP0599159A2 (de) | 1992-11-27 | 1994-06-01 | Hoechst Aktiengesellschaft | a-L-Rhamnosidase zur Gewinnung von Rhamnose, ein Verfahren zur Herstellung und ihre Verwendung |
| WO2000026400A1 (de) * | 1998-10-30 | 2000-05-11 | Merck Patent Gmbh | Verfahren zur enzymatischen spaltung von rutinosiden |
| US6420142B1 (en) | 1998-10-30 | 2002-07-16 | Merck Patent Gesellschaft | Method for enzymatic splitting of rutinosides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH053280B2 (enrdf_load_stackoverflow) | 1993-01-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO1989004831A1 (en) | Glycoside hydrolysis | |
| JPS62293A (ja) | Ｌ−ラムノ−スの製造法 | |
| JP2001258583A (ja) | シキミ酸の精製方法 | |
| EP0533115B1 (en) | Process for production of hydroxocobalamin | |
| JPS6133194A (ja) | 新規アントラサイクリン抗生物質 | |
| US3734828A (en) | Process for the separation and purification of riboflavinyl glycosides | |
| JP2594167B2 (ja) | 新規抗生物質ｓｆ２６９８物質およびその製造法 | |
| JP2001008694A (ja) | Ｄ−キロ−イノシトールの新規製造方法 | |
| JPH05176785A (ja) | アルブチンの製造法 | |
| WO2004108657A1 (en) | Preparation method of valienamine using solid catalysts | |
| CA1275406C (en) | Process for production of anthracycline compound r20x2 | |
| JPH05211883A (ja) | ソホロースの製造方法 | |
| JP3719309B2 (ja) | リビトールの製造方法 | |
| JPS62292A (ja) | Ｌ−ラムノ−スの製造法 | |
| JP2592468B2 (ja) | 新規抗生物質ベナノマイシンａおよびｂならびにその製造法 | |
| JP2512050B2 (ja) | 新規抗かび性抗生物質デキシロシルベナノマイシンｂならびにその製造法 | |
| JP3865781B2 (ja) | Ｋ−２５２ａの精製方法 | |
| JP3026862B2 (ja) | 新規アントラサイクリン化合物 | |
| JP3030896B2 (ja) | Ｗｂ９６８物質群およびその製造法 | |
| JP2887689B2 (ja) | グリチルレチン酸モノグルクロナイドの製造法 | |
| JP2000236894A (ja) | ラディシコールの製造方法 | |
| JPS5819679B2 (ja) | 新規抗生物質及びその製法 | |
| JP2004089014A (ja) | 配糖体の精製方法 | |
| JP2901458B2 (ja) | ゲンチアノースの製造方法 | |
| JPH07110234B2 (ja) | 天然型アブシジン酸の精製法 |