SK3352000A3 - Method of purifying and recovering methylester of n-(3,3- dimethylbutyl)-alpha-l-aspartyl-l-phenylalanine - Google Patents

Method of purifying and recovering methylester of n-(3,3- dimethylbutyl)-alpha-l-aspartyl-l-phenylalanine Download PDF

Info

Publication number: SK3352000A3
Authority: SK; Slovakia
Prior art keywords: aspartyl; methyl ester; dimethylbutyl; phenylalanine; phenylalanine methyl
Prior art date: 1997-09-12

Application number

SK335-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Tadashi Takemoto

Original Assignee

Ajinomoto Kk

Priority date (The priority date 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 date listed.)

1997-09-12

Filing date

1998-08-19

Publication date

2001-12-03

1998-08-19 Application filed by Ajinomoto Kk filed Critical Ajinomoto Kk

2001-12-03 Publication of SK3352000A3 publication Critical patent/SK3352000A3/sk

Links

238000000034 method Methods 0.000 title claims abstract description 32
150000004702 methyl esters Chemical class 0.000 title description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
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 abstract description 27
239000003960 organic solvent Substances 0.000 claims abstract description 25
239000012046 mixed solvent Substances 0.000 claims abstract description 10
239000012535 impurity Substances 0.000 claims abstract description 9
239000010410 layer Substances 0.000 claims description 36
-1 methyl α-L-aspartyl-L-phenylalanine Chemical compound 0.000 claims description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
239000012044 organic layer Substances 0.000 claims description 13
229960005190 phenylalanine Drugs 0.000 claims description 11
239000007864 aqueous solution Substances 0.000 claims description 8
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
COLNVLDHVKWLRT-QMMMGPOBSA-N L-Phenylalanine Natural products OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 5
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 9
238000000746 purification Methods 0.000 abstract description 9
239000013078 crystal Substances 0.000 description 23
239000000203 mixture Substances 0.000 description 20
239000000243 solution Substances 0.000 description 19
239000012452 mother liquor Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000000605 extraction 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
238000011084 recovery Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
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 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Peptides Or Proteins (AREA)
Seasonings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK335-2000A 1997-09-12 1998-08-19 Method of purifying and recovering methylester of n-(3,3- dimethylbutyl)-alpha-l-aspartyl-l-phenylalanine SK3352000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP9247941A JPH1180108A (ja)	1997-09-12	1997-09-12	甘味料の精製法
PCT/JP1998/003682 WO1999014186A1 (en)	1997-09-12	1998-08-19	Method of purifying and recovering sweetener

Publications (1)

Publication Number	Publication Date
SK3352000A3 true SK3352000A3 (en)	2001-12-03

Family

ID=17170837

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK335-2000A SK3352000A3 (en)	1997-09-12	1998-08-19	Method of purifying and recovering methylester of n-(3,3- dimethylbutyl)-alpha-l-aspartyl-l-phenylalanine

Country Status (11)

Country	Link
US (1)	US6316657B1 (cs)
EP (1)	EP1020431A4 (cs)
JP (1)	JPH1180108A (cs)
KR (1)	KR20010023821A (cs)
CN (1)	CN1269781A (cs)
BR (1)	BR9811650A (cs)
CA (1)	CA2301187C (cs)
CZ (1)	CZ2000895A3 (cs)
HU (1)	HUP0004932A3 (cs)
SK (1)	SK3352000A3 (cs)
WO (1)	WO1999014186A1 (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2348021A1 (en)	1998-10-30	2000-05-11	Ajinomoto Co., Inc.	Crystallization processes for the formation of stable crystals of aspartame derivative
AU1832500A (en) *	1998-11-25	2000-06-19	Nutrasweet Company, The	Purification of N-(N-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester via crystallization
US7262624B2 (en) *	2004-12-21	2007-08-28	Formfactor, Inc.	Bi-directional buffer for interfacing test system channel

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2697844B1 (fr)	1992-11-12	1995-01-27	Claude Nofre	Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation.
FR2719590B1 (fr) *	1994-05-09	1996-07-26	Claude Nofre	Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant.
US5728862A (en)	1997-01-29	1998-03-17	The Nutrasweet Company	Method for preparing and purifying an N-alkylated aspartame derivative

1997
- 1997-09-12 JP JP9247941A patent/JPH1180108A/ja active Pending
1998
- 1998-08-19 WO PCT/JP1998/003682 patent/WO1999014186A1/ja not_active Ceased
- 1998-08-19 CN CN98808925A patent/CN1269781A/zh active Pending
- 1998-08-19 EP EP98967108A patent/EP1020431A4/en not_active Withdrawn
- 1998-08-19 KR KR1020007002495A patent/KR20010023821A/ko not_active Withdrawn
- 1998-08-19 SK SK335-2000A patent/SK3352000A3/sk unknown
- 1998-08-19 BR BR9811650-9A patent/BR9811650A/pt not_active IP Right Cessation
- 1998-08-19 CA CA002301187A patent/CA2301187C/en not_active Expired - Fee Related
- 1998-08-19 HU HU0004932A patent/HUP0004932A3/hu unknown
- 1998-08-19 CZ CZ2000895A patent/CZ2000895A3/cs unknown
2000
- 2000-03-13 US US09/525,319 patent/US6316657B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR20010023821A (ko)	2001-03-26
CA2301187A1 (en)	1999-03-25
BR9811650A (pt)	2000-08-08
HUP0004932A3 (en)	2001-06-28
CZ2000895A3 (cs)	2002-01-16
HUP0004932A2 (hu)	2001-05-28
CN1269781A (zh)	2000-10-11
CA2301187C (en)	2007-05-08
WO1999014186A1 (en)	1999-03-25
EP1020431A4 (en)	2001-04-11
EP1020431A1 (en)	2000-07-19
US6316657B1 (en)	2001-11-13
JPH1180108A (ja)	1999-03-26

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