DE3309761C1 - Verfahren zur Herstellung von D,L-Homocystin - Google Patents
Verfahren zur Herstellung von D,L-HomocystinInfo
- Publication number
- DE3309761C1 DE3309761C1 DE3309761A DE3309761A DE3309761C1 DE 3309761 C1 DE3309761 C1 DE 3309761C1 DE 3309761 A DE3309761 A DE 3309761A DE 3309761 A DE3309761 A DE 3309761A DE 3309761 C1 DE3309761 C1 DE 3309761C1
- Authority
- DE
- Germany
- Prior art keywords
- homocystine
- homocysteine
- hydrogen peroxide
- disodium salt
- oxidation
- 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
Links
- ZTVZLYBCZNMWCF-UHFFFAOYSA-N homocystine Chemical compound [O-]C(=O)C([NH3+])CCSSCCC([NH3+])C([O-])=O ZTVZLYBCZNMWCF-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims 2
- FFFHZYDWPBMWHY-UHFFFAOYSA-N HOMOCYSTEINE Chemical compound OC(=O)C(N)CCS FFFHZYDWPBMWHY-UHFFFAOYSA-N 0.000 claims abstract description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 17
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 14
- 230000003647 oxidation Effects 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 5
- 230000017858 demethylation Effects 0.000 description 5
- 238000010520 demethylation reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- ZTVZLYBCZNMWCF-WDSKDSINSA-N L,L-homocystine zwitterion Chemical compound OC(=O)[C@@H](N)CCSSCC[C@H](N)C(O)=O ZTVZLYBCZNMWCF-WDSKDSINSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 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
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 potassium ferricyanide Chemical compound 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3309761A DE3309761C1 (de) | 1983-03-18 | 1983-03-18 | Verfahren zur Herstellung von D,L-Homocystin |
| EP84100179A EP0120182B1 (de) | 1983-03-18 | 1984-01-10 | Verfahren zur Gewinnung von D,L-Homocystin |
| AT84100179T ATE15797T1 (de) | 1983-03-18 | 1984-01-10 | Verfahren zur gewinnung von d,l-homocystin. |
| US06/590,058 US4550199A (en) | 1983-03-18 | 1984-03-15 | Process for obtaining D,L-homocystine (I) |
| JP59049426A JPS59176248A (ja) | 1983-03-18 | 1984-03-16 | Ｄ，ｌ−ホモシスチンの製法 |
| CA000449824A CA1223886A (en) | 1983-03-18 | 1984-03-16 | Process for producing d, l-homocystine (i) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3309761A DE3309761C1 (de) | 1983-03-18 | 1983-03-18 | Verfahren zur Herstellung von D,L-Homocystin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3309761C1 true DE3309761C1 (de) | 1984-03-01 |
Family
ID=6193872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3309761A Expired DE3309761C1 (de) | 1983-03-18 | 1983-03-18 | Verfahren zur Herstellung von D,L-Homocystin |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4550199A (enExample) |
| EP (1) | EP0120182B1 (enExample) |
| JP (1) | JPS59176248A (enExample) |
| AT (1) | ATE15797T1 (enExample) |
| CA (1) | CA1223886A (enExample) |
| DE (1) | DE3309761C1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3620221B2 (ja) * | 1996-11-25 | 2005-02-16 | 三菱化学株式会社 | ホモシスチンの製造法 |
| US6077971A (en) * | 1997-12-05 | 2000-06-20 | Mitsubishi Chemical Corporation | Method for purifying homocystine |
| JP2001302616A (ja) * | 2000-04-26 | 2001-10-31 | Sumitomo Seika Chem Co Ltd | ビスハロフェニルジスルフィド類の製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2406362A (en) * | 1943-11-11 | 1946-08-27 | Du Pont | Process |
| GB621915A (en) * | 1945-12-20 | 1949-04-22 | Merck & Co Inc | Process of preparing penicillamine disulphides |
-
1983
- 1983-03-18 DE DE3309761A patent/DE3309761C1/de not_active Expired
-
1984
- 1984-01-10 AT AT84100179T patent/ATE15797T1/de not_active IP Right Cessation
- 1984-01-10 EP EP84100179A patent/EP0120182B1/de not_active Expired
- 1984-03-15 US US06/590,058 patent/US4550199A/en not_active Expired - Fee Related
- 1984-03-16 CA CA000449824A patent/CA1223886A/en not_active Expired
- 1984-03-16 JP JP59049426A patent/JPS59176248A/ja active Granted
Non-Patent Citations (3)
| Title |
|---|
| Chem. Abstracts, 85, 1976, 29708 * |
| Chem. Abstracts, 89, 1978, 197913 * |
| J.Chem.Soc., London 1964, 869-70 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE15797T1 (de) | 1985-10-15 |
| EP0120182A1 (de) | 1984-10-03 |
| JPH0415780B2 (enExample) | 1992-03-19 |
| US4550199A (en) | 1985-10-29 |
| CA1223886A (en) | 1987-07-07 |
| JPS59176248A (ja) | 1984-10-05 |
| EP0120182B1 (de) | 1985-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8100 | Publication of patent without earlier publication of application | ||
| D1 | Grant (no unexamined application published) patent law 81 | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |