KR860006486A - α-L-아스파르틸-L-페닐알라닌 메틸 에스테르의 제조방법 - Google Patents
α-L-아스파르틸-L-페닐알라닌 메틸 에스테르의 제조방법 Download PDFInfo
- Publication number
- KR860006486A KR860006486A KR1019850009883A KR850009883A KR860006486A KR 860006486 A KR860006486 A KR 860006486A KR 1019850009883 A KR1019850009883 A KR 1019850009883A KR 850009883 A KR850009883 A KR 850009883A KR 860006486 A KR860006486 A KR 860006486A
- Authority
- KR
- South Korea
- Prior art keywords
- aspartyl
- phenylalanine
- formyl
- hydrochloric acid
- acid
- Prior art date
Links
- 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 claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 9
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 6
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- WYYUBJAMROQJSF-QWRGUYRKSA-N (3s)-4-[[(1s)-1-carboxy-2-phenylethyl]amino]-3-formamido-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 WYYUBJAMROQJSF-QWRGUYRKSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 239000007858 starting material Substances 0.000 claims 4
- MTQBJQWJDGTPIL-QWRGUYRKSA-N (2s)-4-[[(1s)-1-carboxy-2-phenylethyl]amino]-2-formamido-4-oxobutanoic acid Chemical compound O=CN[C@H](C(=O)O)CC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 MTQBJQWJDGTPIL-QWRGUYRKSA-N 0.000 claims 3
- 229960005190 phenylalanine Drugs 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
Claims (9)
- 출발물질인 N-포르밀-α-L-아스파르틸-L-페닐알라닌을 산존재하에 메탄올 중에서 처리하여 주요 산물로 α-L-아스파르틸-L-페닐알라닌 디메틸 에스테르를 제조하고, α-L-아스파르틸-L-페닐알라닌 디메틸 에스테르 메탄올 존재하에 염산과 접촉시켜 가수분해한 뒤, 칠전된 α-L-아스파르틸-L-페닐알라닌 메틸 에스테르 히드로클로라이드를 분리하고, 이 히드로클로라이드를 중화함을 특징으로 하는, α-L-아스파르틸-L-페닐알라닌 메틸 에스테르의 제조방법.
- 제 1 항 있어서, 출발물질로 사용된 N-포르밀-α-L-아스파르틸-L-페닐알라닌이 30중량% 이하의 N-포르밀-β-L-아스파르틸-L-페닐알라닌을 함유하는 방법.
- 제 1 또는 2항에 있어서, 산이 무기산인 방법.
- 제 1 또는 2항에 있어서, 산이 유기술폰산인 방법.
- 제 1 또는 2항에 있어서, 10-70℃의 온도로 처리하여 α-L-아스파르틸-L-페닐알라닌 디메틸 에스테르를 제조하는 방법.
- 제 1 또는 2항에 있어서, α-L-아스파르틸-L-페닐알라닌 디메틸 에스테르와 접촉시키는 염산의 농도가 [염산/(염산+수용액)]×100으로 3-30중량%인 방법.
- 제 1 또는 2항에 있어서, 사용된 염산의 양이 출발물질로 사용한 N-포르밀-α-L-아스파르틸-L-페닐알라닌의 몰 당, 또는 β-이성질체가 함유된 경우, N-포르밀-α-L-아스파르틸-L-페닐알라닌과 N-포르밀-β-L-아스파르틸-L-페닐알라닌의 혼합물의 몰당 0.5-10몰인 방법.
- 제 1 또는 2항에 있어서, α-L-아스파르틸-L-페닐 알라닌 디메틸 에스테르를 염산과 접촉시킴으로써 가수분해시켜 α-L-아스파르틸-L-페닐알라닌 메틸 메스테르 염산염을 제조하는데 필요한 메탄올의 양이 출발물질로 사용한 N-포르밀-α-L-아스파르틸-L-페닐알라닌의 물 당, 또는 β-이성질체가 함유된 경우, N-포르밀-α-L-아스파르틸-L-페닐알라닌과 N-포르밀-β-L-아스파르틸-L-페닐알라닌의 혼합물의 몰당 5몰 이하인 방법.
- 제 1 또는 2항에 있어서, α-L-아스파르틸-L-페닐알라닌 디메틸 에스테르와 염산을 접촉시키는 온도가 0- 50℃인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP273701 | 1984-12-27 | ||
JP59273701A JPS61152698A (ja) | 1984-12-27 | 1984-12-27 | α−L−アスパルチル−L−フエニルアラニンメチルエステルの製造法 |
JP60036530A JPS61197592A (ja) | 1985-02-27 | 1985-02-27 | α−L−アスパルチル−L−フエニルアラニンメチルエステルの製造方法 |
JP36530 | 1985-02-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR860006486A true KR860006486A (ko) | 1986-09-11 |
KR890005064B1 KR890005064B1 (ko) | 1989-12-09 |
Family
ID=26375586
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019850009883A KR890005064B1 (ko) | 1984-12-27 | 1985-12-27 | α-L-아스파르틸-L-페닐알라닌 메틸 에스테르의 제조방법 |
Country Status (6)
Country | Link |
---|---|
US (1) | US4801732A (ko) |
EP (1) | EP0187530A3 (ko) |
KR (1) | KR890005064B1 (ko) |
BR (1) | BR8506513A (ko) |
CA (1) | CA1277098C (ko) |
ES (1) | ES8703487A1 (ko) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU561384B2 (en) * | 1985-03-26 | 1987-05-07 | Mitsui Toatsu Chemicals Inc. | Preparation of -l-aspartyl-l-phenylalanine methyl ester or hydrochloride thereof |
DE3780585T2 (de) * | 1986-12-05 | 1993-03-18 | Mitsui Toatsu Chemicals | Herstellung von alpha-l-aspartyl-l-phenylalanin-methylester oder deren hydrohalide. |
NL8701035A (nl) * | 1987-05-01 | 1988-12-01 | Stamicarbon | Werkwijze voor de bereiding van aspartylfenylalaninemethylester uit n-formylaspartylfenylalaninemethylester. |
US4892820A (en) * | 1987-06-10 | 1990-01-09 | The Nutrasweet Company | Solvent system for enzymatic coupling process |
JP2979761B2 (ja) * | 1991-05-23 | 1999-11-15 | 味の素株式会社 | α−L−アスパルチル−L−フェニルアラニンメチルエステル塩酸塩の製造法 |
JP3239452B2 (ja) * | 1992-08-05 | 2001-12-17 | 味の素株式会社 | α−L−アスパルチル−L−フェニルアラニンメチルエステル塩酸塩の製造法 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS461370Y1 (ko) * | 1966-05-25 | 1971-01-19 | ||
BE791544A (fr) * | 1971-11-19 | 1973-05-17 | Stamicarbon | Preparation d'esters alkyliques de dipeptide |
JPS4896557A (ko) * | 1972-03-22 | 1973-12-10 | ||
CA1028197A (en) * | 1973-04-02 | 1978-03-21 | Jeffrey H. Berg | Concentrated liquid low calorie sweetener |
US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
JPS5140069A (ko) * | 1974-10-02 | 1976-04-03 | Hitachi Ltd | |
JPS5823380B2 (ja) * | 1974-12-05 | 1983-05-14 | 味の素株式会社 | ホルミルキノ ダツリホウ |
JPS51113841A (en) * | 1975-03-28 | 1976-10-07 | Ajinomoto Co Inc | Process for preparing lower alkyl esters of n-formyl-alpha -l-aspartyl-l-phenylalanine |
US4088649A (en) * | 1975-07-02 | 1978-05-09 | Firmenich S.A. | Process for preparing a diketo-piperazine |
JPS5223001A (en) * | 1975-08-14 | 1977-02-21 | Ajinomoto Co Inc | Process for elimination of formyl group |
MX4704E (es) * | 1976-12-27 | 1982-08-04 | Monsanto Co | Procedimiento mejorado para la preparacion de ester metilico de alfa-l-aspartil-l-fenilalanina |
JPS58185545A (ja) * | 1982-04-22 | 1983-10-29 | Ajinomoto Co Inc | α−L−アスパルチル−L−フエニルアラニンメチルエステルまたはその塩酸塩の製法 |
GB8300810D0 (en) * | 1983-01-13 | 1983-02-16 | Erba Farmitalia | Aspartame synthesis |
JPS59219258A (ja) * | 1983-05-28 | 1984-12-10 | Ajinomoto Co Inc | 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 |
JPH0613550B2 (ja) * | 1983-06-03 | 1994-02-23 | 味の素株式会社 | α―L―アスパルチル―L―フェニルアラニン―低級アルキルエステルの製造法 |
JPS59225152A (ja) * | 1983-06-02 | 1984-12-18 | Ajinomoto Co Inc | 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 |
JPS6050200A (ja) * | 1983-08-30 | 1985-03-19 | Nippon Kokan Kk <Nkk> | 金属ストリップのクリーニング洗浄液の浄化装置 |
JPS60174799A (ja) * | 1984-02-21 | 1985-09-09 | Ajinomoto Co Inc | α−L−アスパルチル−L−フエニルアラニンメチルエステルの製造法 |
-
1985
- 1985-12-20 ES ES550282A patent/ES8703487A1/es not_active Expired
- 1985-12-20 CA CA000498219A patent/CA1277098C/en not_active Expired - Lifetime
- 1985-12-24 EP EP85309481A patent/EP0187530A3/en not_active Withdrawn
- 1985-12-26 BR BR8506513A patent/BR8506513A/pt unknown
- 1985-12-27 KR KR1019850009883A patent/KR890005064B1/ko not_active IP Right Cessation
-
1988
- 1988-03-22 US US07/171,134 patent/US4801732A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0187530A2 (en) | 1986-07-16 |
US4801732A (en) | 1989-01-31 |
EP0187530A3 (en) | 1988-07-20 |
KR890005064B1 (ko) | 1989-12-09 |
ES8703487A1 (es) | 1987-03-01 |
CA1277098C (en) | 1990-11-27 |
BR8506513A (pt) | 1986-09-02 |
ES550282A0 (es) | 1987-03-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR860003013A (ko) | 안정화된 피록시캄 주사용액의 제조방법 | |
KR890002137A (ko) | 아지트로마이신 이수화물 | |
KR830001375A (ko) | 박테리아 발효에 의한 다당류 s-60의 제조방법 | |
KR840009295A (ko) | α-L-아스파르틸-L-페닐아라딘 메틸에스테르 및 그의 염산염의 제조방법 | |
JPS54122253A (en) | Preparation of cis-alkylcyclohexanol | |
KR860006486A (ko) | α-L-아스파르틸-L-페닐알라닌 메틸 에스테르의 제조방법 | |
KR870003220A (ko) | 희토류 광석의 처리방법 | |
GB1546979A (en) | Process for the preparation of alpha-l-aspartyl-l-phenylallanine methyl ester | |
KR860007284A (ko) | α-L-아스파르틸-L-페닐알라닌 메틸에스테르 또는 그의 염산염의 제조방법 | |
HUP0102098A2 (hu) | Eljárás gél előállítására polivinilalkoholból, és az eljárás szerint előállított, nagy mechanikai stabilitású gél | |
ATE38513T1 (de) | Herstellung von mexamin. | |
JPS5535059A (en) | Preparation of lower alkyl ester of alpha-l-aspartyl-l- phenylalanine | |
JPS53135925A (en) | Decomposition of microbial cells | |
KR840006197A (ko) | N-포르밀-l-아스파르트산 무수물의 제조방법 | |
KR910011898A (ko) | 데스(64,65)-프로인슐린의 제조방법 | |
JPS548688A (en) | Novel cation-modified polypeptide and its preparation | |
KR850001526A (ko) | 분말상 섬유소 글리코올 칼슘의 제조법 | |
KR890006561A (ko) | 디알킬 디클로로숙시네이트의 개선된 제조방법 | |
KR890001470A (ko) | 전분질 식물체를 원료로 한 기호성 청량음료 원액의 제조방법 | |
KR900004712A (ko) | 하이드로스민의 제조방법 | |
GB1491772A (en) | Method for purifying 11-cyano-undecanoic acid | |
KR870005987A (ko) | N-[[(s)-4-옥소-2-아제티디닐]-카르보닐]-l-히스티딜-l-프롤린아미드의 신규 결정의 제조방법 | |
KR880007003A (ko) | α-L-아스파르틸-L-페닐알라닌메틸에스테르 또는 그 할로겐화수소산의 제법 | |
KR890000414A (ko) | 엘-시스틴의 제조방법 | |
KR910012255A (ko) | 연속농축 및 결정화법에 의한 l-라이신의 제조방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19851227 |
|
PA0201 | Request for examination | ||
PG1501 | Laying open of application | ||
E902 | Notification of reason for refusal | ||
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19870324 Patent event code: PE09021S01D |
|
G160 | Decision to publish patent application | ||
PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19891108 |
|
E701 | Decision to grant or registration of patent right | ||
PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19900228 |
|
GRNT | Written decision to grant | ||
PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19900424 Patent event code: PR07011E01D |
|
PR1002 | Payment of registration fee |
Payment date: 19900424 End annual number: 3 Start annual number: 1 |
|
LAPS | Lapse due to unpaid annual fee | ||
PC1903 | Unpaid annual fee |