JPS59225152A - α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法 - Google Patents
α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法Info
- Publication number
- JPS59225152A JPS59225152A JP58098716A JP9871683A JPS59225152A JP S59225152 A JPS59225152 A JP S59225152A JP 58098716 A JP58098716 A JP 58098716A JP 9871683 A JP9871683 A JP 9871683A JP S59225152 A JPS59225152 A JP S59225152A
- Authority
- JP
- Japan
- Prior art keywords
- methyl ester
- aspartyl
- hydrochloride
- phenylalanine
- apm
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 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 title abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000012046 mixed solvent Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 150000002148 esters Chemical group 0.000 claims abstract 3
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 235000003599 food sweetener Nutrition 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 239000003765 sweetening agent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 17
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 108010016626 Dipeptides Proteins 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- REJGTIJQSDMJJZ-YNDOSBHVSA-N (3S)-3-amino-4-[1-[(1R)-1-amino-1-carboxyethyl]cyclohexa-2,4-dien-1-yl]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](N)C(=O)C1([C@@](N)(C(O)=O)C)CC=CC=C1 REJGTIJQSDMJJZ-YNDOSBHVSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Peptides Or Proteins (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58098716A JPS59225152A (ja) | 1983-06-02 | 1983-06-02 | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法 |
| US06/611,548 US4618695A (en) | 1983-06-02 | 1984-05-17 | Method of preparing methyl ester and its hydrochloride |
| IE1258/84A IE57518B1 (en) | 1983-06-02 | 1984-05-21 | Method of preparing alpha-l-aspartyl-l-phenylalanine methyl ester and its hydrochloride |
| DE8484303418T DE3467352D1 (en) | 1983-06-02 | 1984-05-21 | Method of preparing alpha-l-aspartyl-l-phenylalanine methyl ester and its hydrochloride |
| EP84303418A EP0127977B1 (en) | 1983-06-02 | 1984-05-21 | Method of preparing alpha-l-aspartyl-l-phenylalanine methyl ester and its hydrochloride |
| CA000455147A CA1268598A (en) | 1983-06-02 | 1984-05-25 | METHOD OF PREPARING .alpha.-L-ASPARTYL-L-PHENYLALANINE METHYL ESTER AND ITS HYDROCHLORIDE |
| KR1019840003049A KR920002337B1 (ko) | 1983-06-02 | 1984-06-01 | α-L-아스파르틸-L-페닐알라닌 메틸 에스테르 및 이의 염산염의 제조방법 |
| KR1019920001929A KR920003333B1 (ko) | 1983-06-02 | 1992-02-11 | α-L-아스파르틸-L-페닐알라닌 β-저급 알킬 에스테르의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58098716A JPS59225152A (ja) | 1983-06-02 | 1983-06-02 | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59225152A true JPS59225152A (ja) | 1984-12-18 |
| JPH0441155B2 JPH0441155B2 (enrdf_load_stackoverflow) | 1992-07-07 |
Family
ID=14227241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58098716A Granted JPS59225152A (ja) | 1983-06-02 | 1983-06-02 | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステル又はその塩酸塩の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59225152A (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4745210A (en) * | 1984-12-17 | 1988-05-17 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of N-formyl-α-aspartyl phenylalanine |
| US4778916A (en) * | 1985-03-26 | 1988-10-18 | Mitsui Toatsu Chemicals, Inc. | Preparation process of α-L-aspartyl-L-phenylalanine methyl ester or hydrochloride thereof |
| US4801732A (en) * | 1984-12-27 | 1989-01-31 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of α-L-aspartyl-L-phenylalanine methyl ester |
| US4918216A (en) * | 1986-12-05 | 1990-04-17 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of α-l-aspartyl-l-phenyl-alanine methyl ester or hydrohalide thereof |
| US4962222A (en) * | 1986-12-19 | 1990-10-09 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of α-l-aspartyl-l-phenylalanine methyl ester having low hygroscopicity |
| JP2005058212A (ja) * | 2003-01-24 | 2005-03-10 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フェニルアラニン−β−エステルの製造方法およびα−Ｌ−アスパルチル−Ｌ−フェニルアラニン−α−メチルエステルの製造方法 |
| EP1587941A4 (en) * | 2003-01-24 | 2006-06-21 | Ajinomoto Kk | PROCESS FOR PRODUCING (A) -L-ASPARTYL-L-PHENYLALANINE- (B) -ESTER AND PROCESS FOR PRODUCING (A) -L-ASPARTYL-L-PHENYLALANINE- (A) -METHYL ESTER |
| JP2010029213A (ja) * | 2002-07-26 | 2010-02-12 | Ajinomoto Co Inc | 新規ペプチド生成酵素遺伝子 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5071642A (enrdf_load_stackoverflow) * | 1973-11-05 | 1975-06-13 | ||
| JPS5382752A (en) * | 1976-12-27 | 1978-07-21 | Monsanto Co | Improved method of preparing alphaa aspartyl l phenylalanin methyl ester |
-
1983
- 1983-06-02 JP JP58098716A patent/JPS59225152A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5071642A (enrdf_load_stackoverflow) * | 1973-11-05 | 1975-06-13 | ||
| JPS5382752A (en) * | 1976-12-27 | 1978-07-21 | Monsanto Co | Improved method of preparing alphaa aspartyl l phenylalanin methyl ester |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4745210A (en) * | 1984-12-17 | 1988-05-17 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of N-formyl-α-aspartyl phenylalanine |
| US4801732A (en) * | 1984-12-27 | 1989-01-31 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of α-L-aspartyl-L-phenylalanine methyl ester |
| US4778916A (en) * | 1985-03-26 | 1988-10-18 | Mitsui Toatsu Chemicals, Inc. | Preparation process of α-L-aspartyl-L-phenylalanine methyl ester or hydrochloride thereof |
| US4918216A (en) * | 1986-12-05 | 1990-04-17 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of α-l-aspartyl-l-phenyl-alanine methyl ester or hydrohalide thereof |
| US4962222A (en) * | 1986-12-19 | 1990-10-09 | Mitsui Toatsu Chemicals, Incorporated | Preparation process of α-l-aspartyl-l-phenylalanine methyl ester having low hygroscopicity |
| JP2010029213A (ja) * | 2002-07-26 | 2010-02-12 | Ajinomoto Co Inc | 新規ペプチド生成酵素遺伝子 |
| JP2010029214A (ja) * | 2002-07-26 | 2010-02-12 | Ajinomoto Co Inc | 新規ペプチド生成酵素遺伝子 |
| EP1587941A4 (en) * | 2003-01-24 | 2006-06-21 | Ajinomoto Kk | PROCESS FOR PRODUCING (A) -L-ASPARTYL-L-PHENYLALANINE- (B) -ESTER AND PROCESS FOR PRODUCING (A) -L-ASPARTYL-L-PHENYLALANINE- (A) -METHYL ESTER |
| JP2005058212A (ja) * | 2003-01-24 | 2005-03-10 | Ajinomoto Co Inc | α−Ｌ−アスパルチル−Ｌ−フェニルアラニン−β−エステルの製造方法およびα−Ｌ−アスパルチル−Ｌ−フェニルアラニン−α−メチルエステルの製造方法 |
| EP2157188A1 (en) * | 2003-01-24 | 2010-02-24 | Ajinomoto Co., Inc. | Method for producing alpha-L-Aspartyl-L-phenylalanine-Beta-ester and method for producing alpha-L-aspartyl-L-phenylalanine-alpha-methyl ester |
| EP2166109A1 (en) * | 2003-01-24 | 2010-03-24 | Ajinomoto Co., Inc. | Method for producing alpha-L-aspartyl-L-phenylalanine-beta-ester and method for producing alpha-L-aspartyl-L-phenylalanine-alpha-methyl ester |
| EP2180061A1 (en) * | 2003-01-24 | 2010-04-28 | Ajinomoto Co., Inc. | Method for producing alpha-L-aspartyl-L-phenylalanine-beta-ester and method for producing alpha-L-aspartyl-L-phenylalanine-alpha-methyl ester |
| EP2180059A1 (en) * | 2003-01-24 | 2010-04-28 | Ajinomoto Co., Inc. | Method for producing alpha-L-aspartyl-L-phenylalanine-beta-ester and method for producing alpha-L-aspartyl-L-phenylalanine-alpha-methyl ester |
| EP2180060A1 (en) * | 2003-01-24 | 2010-04-28 | Ajinomoto Co., Inc. | Method for produding alpha-L-aspartyl-L-phenylalanine-beta-ester and method for producing alpha-L-aspartyl-L-phenylalanine-alpha-methyl ester |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0441155B2 (enrdf_load_stackoverflow) | 1992-07-07 |
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