JP6483250B2 - エルゴチオネインおよび関連化合物の合成方法 - Google Patents
エルゴチオネインおよび関連化合物の合成方法 Download PDFInfo
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- JP6483250B2 JP6483250B2 JP2017515766A JP2017515766A JP6483250B2 JP 6483250 B2 JP6483250 B2 JP 6483250B2 JP 2017515766 A JP2017515766 A JP 2017515766A JP 2017515766 A JP2017515766 A JP 2017515766A JP 6483250 B2 JP6483250 B2 JP 6483250B2
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- ergothioneine
- compound
- sulfoxide
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- 229940093497 ergothioneine Drugs 0.000 title claims description 71
- 238000000034 method Methods 0.000 title claims description 50
- SSISHJJTAXXQAX-ZETCQYMHSA-N L-ergothioneine Chemical compound C[N+](C)(C)[C@H](C([O-])=O)CC1=CNC(=S)N1 SSISHJJTAXXQAX-ZETCQYMHSA-N 0.000 title claims description 44
- 150000001875 compounds Chemical class 0.000 title claims description 32
- 230000002194 synthesizing effect Effects 0.000 title claims description 6
- -1 β-amino-β-carboxyethyl Chemical group 0.000 claims description 79
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 44
- 150000003462 sulfoxides Chemical class 0.000 claims description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 claims description 27
- 108090000790 Enzymes Proteins 0.000 claims description 25
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- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 claims description 22
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 claims description 22
- 229960001327 pyridoxal phosphate Drugs 0.000 claims description 22
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229960002885 histidine Drugs 0.000 claims description 16
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- 150000003457 sulfones Chemical class 0.000 claims description 14
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 13
- 150000002596 lactones Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- RAKGGEXKAWATLR-AWEZNQCLSA-N C(C1=CC=CC=C1)N1C=NC(=C1)C[C@@H](C(=O)O)N(C)C Chemical compound C(C1=CC=CC=C1)N1C=NC(=C1)C[C@@H](C(=O)O)N(C)C RAKGGEXKAWATLR-AWEZNQCLSA-N 0.000 claims description 6
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 5
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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| GBGB1416678.9A GB201416678D0 (en) | 2014-09-22 | 2014-09-22 | Process For Synthesizing Ergothioneine And Its Intermediates |
| PCT/IB2015/001668 WO2016046618A1 (en) | 2014-09-22 | 2015-09-22 | Process for synthesizing ergothioneine and related compounds |
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| JP2017536086A5 JP2017536086A5 (enExample) | 2018-11-01 |
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| CN105949130B (zh) * | 2016-04-29 | 2018-10-19 | 华南农业大学 | 一种利用超声-微波辅助结合真空冷冻干燥提取食用菌麦角硫因的方法 |
| CN111170945B (zh) * | 2020-01-15 | 2022-03-29 | 中国科学院西北高原生物研究所 | 黄蘑菇中天然抗氧化氨基酸衍生物的分离工艺及其应用 |
| JP6864131B1 (ja) * | 2020-03-04 | 2021-04-28 | 長瀬産業株式会社 | Ｌ−エルゴチオネイン含有組成物 |
| CN111574458B (zh) * | 2020-06-11 | 2023-04-07 | 上海克琴科技有限公司 | 一种麦角硫因的合成方法 |
| CN114409608B (zh) * | 2022-01-24 | 2022-09-02 | 广州金娜宝生物科技有限公司 | 一种麦角硫因的合成方法 |
| CN119032084A (zh) * | 2022-04-22 | 2024-11-26 | 南京纽邦生物科技有限公司 | 麦角硫因的化学合成方法和使用方法 |
| CN116102502A (zh) * | 2022-11-28 | 2023-05-12 | 南京艾希帝生物科技有限公司 | 一种麦角硫因的合成方法 |
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| FR2950889B1 (fr) * | 2009-10-06 | 2011-11-18 | Tetrahedron | Procede de synthese de l'ergothioneine et analogues |
| KR102116734B1 (ko) * | 2012-12-21 | 2020-05-29 | 핑후아 리오우 | 대사 공학을 통한 에르고티오네인 생성 |
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- 2015-09-22 WO PCT/IB2015/001668 patent/WO2016046618A1/en not_active Ceased
- 2015-09-22 US US15/513,237 patent/US9908854B2/en active Active
- 2015-09-22 CN CN201580062451.0A patent/CN107108520B/zh active Active
- 2015-09-22 EP EP15778015.6A patent/EP3197874B1/en active Active
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| US20170305865A1 (en) | 2017-10-26 |
| JP2017536086A (ja) | 2017-12-07 |
| US9908854B2 (en) | 2018-03-06 |
| CN107108520A (zh) | 2017-08-29 |
| WO2016046618A1 (en) | 2016-03-31 |
| GB201416678D0 (en) | 2014-11-05 |
| CN107108520B (zh) | 2018-11-02 |
| EP3197874A1 (en) | 2017-08-02 |
| EP3197874B1 (en) | 2019-04-24 |
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