JPS6274296A - α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの製造方法 - Google Patents
α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの製造方法Info
- Publication number
- JPS6274296A JPS6274296A JP21173085A JP21173085A JPS6274296A JP S6274296 A JPS6274296 A JP S6274296A JP 21173085 A JP21173085 A JP 21173085A JP 21173085 A JP21173085 A JP 21173085A JP S6274296 A JPS6274296 A JP S6274296A
- Authority
- JP
- Japan
- Prior art keywords
- acetyl
- phenylalanine
- acid
- alkyl ester
- methyl ester
- 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
- 229960005190 phenylalanine Drugs 0.000 title claims abstract description 19
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-Phenylalanine Natural products OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title claims abstract description 14
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 18
- 108090001109 Thermolysin Proteins 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 11
- 108090000790 Enzymes Proteins 0.000 claims abstract description 9
- 102000004190 Enzymes Human genes 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 5
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract 2
- 229960005261 aspartic acid Drugs 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 5
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 claims description 5
- 150000004702 methyl esters Chemical group 0.000 claims description 4
- -1 L-phenylalanine ester Chemical class 0.000 claims description 3
- 125000003047 N-acetyl group Chemical group 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 108010016626 Dipeptides Proteins 0.000 claims 2
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 238000006664 bond formation reaction Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 10
- 125000006239 protecting group Chemical group 0.000 abstract description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract description 2
- 235000019253 formic acid Nutrition 0.000 abstract description 2
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 abstract 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007787 solid Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- SWVMLNPDTIFDDY-FVGYRXGTSA-N methyl (2s)-2-amino-3-phenylpropanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=CC=C1 SWVMLNPDTIFDDY-FVGYRXGTSA-N 0.000 description 4
- 108091005804 Peptidases Proteins 0.000 description 3
- 102000035195 Peptidases Human genes 0.000 description 3
- 238000006911 enzymatic reaction Methods 0.000 description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- 241001474791 Proboscis Species 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002993 phenylalanine derivatives Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- IZNCNDSZTRKDQH-MERQFXBCSA-N propan-2-yl (2s)-2-amino-3-phenylpropanoate;hydrochloride Chemical compound Cl.CC(C)OC(=O)[C@@H](N)CC1=CC=CC=C1 IZNCNDSZTRKDQH-MERQFXBCSA-N 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21173085A JPS6274296A (ja) | 1985-09-25 | 1985-09-25 | α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21173085A JPS6274296A (ja) | 1985-09-25 | 1985-09-25 | α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6274296A true JPS6274296A (ja) | 1987-04-06 |
| JPH0525480B2 JPH0525480B2 (enrdf_load_stackoverflow) | 1993-04-13 |
Family
ID=16610644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21173085A Granted JPS6274296A (ja) | 1985-09-25 | 1985-09-25 | α―Ｌ―アスパルチル―Ｌ―フェニルアラニンメチルエステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6274296A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4992552A (en) * | 1988-08-31 | 1991-02-12 | Eastman Kodak Company | Process for preparation of amino acids |
| US5144073A (en) * | 1988-08-31 | 1992-09-01 | Hubbs John C | Process for preparation of dipeptides |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
| JPS5392729A (en) * | 1977-01-27 | 1978-08-15 | Toyo Soda Mfg Co Ltd | Adduct of dipeptide derivatives and amino acid derivatives and process for their preparation |
-
1985
- 1985-09-25 JP JP21173085A patent/JPS6274296A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
| JPS5392729A (en) * | 1977-01-27 | 1978-08-15 | Toyo Soda Mfg Co Ltd | Adduct of dipeptide derivatives and amino acid derivatives and process for their preparation |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4992552A (en) * | 1988-08-31 | 1991-02-12 | Eastman Kodak Company | Process for preparation of amino acids |
| US5144073A (en) * | 1988-08-31 | 1992-09-01 | Hubbs John C | Process for preparation of dipeptides |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0525480B2 (enrdf_load_stackoverflow) | 1993-04-13 |
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