JPS63215656A - ε−アシルリジンまたはδ−アシルオルニチンの製造方法 - Google Patents
ε−アシルリジンまたはδ−アシルオルニチンの製造方法Info
- Publication number
- JPS63215656A JPS63215656A JP4843287A JP4843287A JPS63215656A JP S63215656 A JPS63215656 A JP S63215656A JP 4843287 A JP4843287 A JP 4843287A JP 4843287 A JP4843287 A JP 4843287A JP S63215656 A JPS63215656 A JP S63215656A
- Authority
- JP
- Japan
- Prior art keywords
- lysine
- group
- ornithine
- acyl
- ion
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- -1 sulfonium compound Chemical class 0.000 claims abstract description 21
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000004472 Lysine Substances 0.000 claims abstract description 18
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims abstract description 14
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229960003104 ornithine Drugs 0.000 claims abstract description 14
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 3
- 239000010842 industrial wastewater Substances 0.000 abstract description 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000004065 wastewater treatment Methods 0.000 abstract 1
- 229960003646 lysine Drugs 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229940116318 copper carbonate Drugs 0.000 description 3
- GEZOTWYUIKXWOA-UHFFFAOYSA-L copper;carbonate Chemical compound [Cu+2].[O-]C([O-])=O GEZOTWYUIKXWOA-UHFFFAOYSA-L 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GGTYBZJRPHEQDG-WCCKRBBISA-N (2s)-2,5-diaminopentanoic acid hydrochloride Chemical compound Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-N 0.000 description 2
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 2
- NPUVYHNDWLTMSW-UHFFFAOYSA-N OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.[AsH3].[AsH3] Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.[AsH3].[AsH3] NPUVYHNDWLTMSW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 229960005337 lysine hydrochloride Drugs 0.000 description 2
- 229960003244 ornithine hydrochloride Drugs 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VSJVTIUBGGZOSC-VUWPPUDQSA-N (2s)-2,5-diamino-6-oxo-6-phenylmethoxyhexanoic acid Chemical compound OC(=O)[C@@H](N)CCC(N)C(=O)OCC1=CC=CC=C1 VSJVTIUBGGZOSC-VUWPPUDQSA-N 0.000 description 1
- JVEUTCWLEJSEDI-PXYINDEMSA-N (2s)-2,6-diamino-7-oxo-7-phenylmethoxyheptanoic acid Chemical compound OC(=O)[C@@H](N)CCCC(N)C(=O)OCC1=CC=CC=C1 JVEUTCWLEJSEDI-PXYINDEMSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- 229910017974 NH40H Inorganic materials 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- MKOYQDCOZXHZSO-UHFFFAOYSA-N [Cu].[Cu].[Cu].[As] Chemical compound [Cu].[Cu].[Cu].[As] MKOYQDCOZXHZSO-UHFFFAOYSA-N 0.000 description 1
- LAISNASYKAIAIK-UHFFFAOYSA-N [S].[As] Chemical compound [S].[As] LAISNASYKAIAIK-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ZWNOVERPMUJRKE-UHFFFAOYSA-N dimethyl-(4-phenylmethoxycarbonyloxyphenyl)sulfanium Chemical compound C1=CC([S+](C)C)=CC=C1OC(=O)OCC1=CC=CC=C1 ZWNOVERPMUJRKE-UHFFFAOYSA-N 0.000 description 1
- TZNVSQKDTQRDJF-UHFFFAOYSA-M dimethyl-(4-phenylmethoxycarbonyloxyphenyl)sulfanium;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC([S+](C)C)=CC=C1OC(=O)OCC1=CC=CC=C1 TZNVSQKDTQRDJF-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- JQQHKTPQFWSNBC-UHFFFAOYSA-J hydrogen carbonate thorium(4+) Chemical compound [Th+4].OC([O-])=O.OC([O-])=O.OC([O-])=O.OC([O-])=O JQQHKTPQFWSNBC-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4843287A JPS63215656A (ja) | 1987-03-02 | 1987-03-02 | ε−アシルリジンまたはδ−アシルオルニチンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4843287A JPS63215656A (ja) | 1987-03-02 | 1987-03-02 | ε−アシルリジンまたはδ−アシルオルニチンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63215656A true JPS63215656A (ja) | 1988-09-08 |
| JPH0576936B2 JPH0576936B2 (enrdf_load_stackoverflow) | 1993-10-25 |
Family
ID=12803191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4843287A Granted JPS63215656A (ja) | 1987-03-02 | 1987-03-02 | ε−アシルリジンまたはδ−アシルオルニチンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63215656A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001088017A1 (fr) * | 2000-05-18 | 2001-11-22 | Hisamitsu Pharmaceutical Co., Inc. | Derives de polypeptides et transporteurs d'acides nucleiques contenant ces derives |
-
1987
- 1987-03-02 JP JP4843287A patent/JPS63215656A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001088017A1 (fr) * | 2000-05-18 | 2001-11-22 | Hisamitsu Pharmaceutical Co., Inc. | Derives de polypeptides et transporteurs d'acides nucleiques contenant ces derives |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0576936B2 (enrdf_load_stackoverflow) | 1993-10-25 |
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