JPS59198994A - 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 - Google Patents
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Info
- Publication number
- JPS59198994A JPS59198994A JP7555983A JP7555983A JPS59198994A JP S59198994 A JPS59198994 A JP S59198994A JP 7555983 A JP7555983 A JP 7555983A JP 7555983 A JP7555983 A JP 7555983A JP S59198994 A JPS59198994 A JP S59198994A
- Authority
- JP
- Japan
- Prior art keywords
- genus
- methyl ester
- phenylalanine methyl
- aspartic acid
- 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
- 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 abstract description 29
- 238000002360 preparation method Methods 0.000 title description 2
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 claims abstract description 7
- 241000590020 Achromobacter Species 0.000 claims abstract description 4
- 241000589565 Flavobacterium Species 0.000 claims abstract description 4
- 241000192041 Micrococcus Species 0.000 claims abstract description 4
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims abstract description 3
- 244000005700 microbiome Species 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 241000186216 Corynebacterium Species 0.000 claims description 3
- 241001527609 Cryptococcus Species 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 241000588722 Escherichia Species 0.000 claims description 2
- 241000502261 Endomyces sp. Species 0.000 claims 1
- 241000159512 Geotrichum Species 0.000 claims 1
- 241001079965 Trichosporon sp. Species 0.000 claims 1
- 241001148118 Xanthomonas sp. Species 0.000 claims 1
- 229960005261 aspartic acid Drugs 0.000 abstract description 21
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 abstract description 15
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 abstract description 14
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 abstract description 14
- 230000000813 microbial effect Effects 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 241000589634 Xanthomonas Species 0.000 abstract description 2
- 241001337994 Cryptococcus <scale insect> Species 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 235000003599 food sweetener Nutrition 0.000 abstract 1
- 239000003765 sweetening agent Substances 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012736 aqueous medium Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910001410 inorganic ion Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- -1 N-protected L-aspartic anhydride Chemical class 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- 241000186249 Corynebacterium sp. Species 0.000 description 1
- 241000257465 Echinoidea Species 0.000 description 1
- 241000178951 Endomyces Species 0.000 description 1
- 241000230562 Flavobacteriia Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 241000223252 Rhodotorula Species 0.000 description 1
- 241000222068 Sporobolomyces <Sporidiobolaceae> Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000223230 Trichosporon Species 0.000 description 1
- JETSKDPKURDVNI-UHFFFAOYSA-N [C].[Ca] Chemical compound [C].[Ca] JETSKDPKURDVNI-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 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 description 1
- 239000000872 buffer Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7555983A JPS59198994A (ja) | 1983-04-28 | 1983-04-28 | 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 |
| EP84302577A EP0124313B1 (en) | 1983-04-28 | 1984-04-16 | Process for the production of l-aspartyl-l-phenylalanine methyl ester or l-aspartyl-l-phenylalanine |
| DE8484302577T DE3479214D1 (en) | 1983-04-28 | 1984-04-16 | Process for the production of l-aspartyl-l-phenylalanine methyl ester or l-aspartyl-l-phenylalanine |
| CA000452205A CA1237018A (en) | 1983-04-28 | 1984-04-17 | Process for the production of l-aspartyl-l- phenylalanine methyl ester or l-aspartyl-l- phenylalanine |
| US06/604,523 US4711846A (en) | 1983-04-28 | 1984-04-27 | Process for the production of L-aspartyl-L-phenylalanine methy ester or L-aspartyl-L-phenylalanine |
| KR1019840002291A KR920002453B1 (ko) | 1983-04-28 | 1984-04-28 | L-아스파틸-l-페닐알라닌 메틸 에스테르 또는 l-아스파틸-l-페닐알라닌의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7555983A JPS59198994A (ja) | 1983-04-28 | 1983-04-28 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59198994A true JPS59198994A (ja) | 1984-11-10 |
| JPH0215196B2 JPH0215196B2 (enrdf_load_stackoverflow) | 1990-04-11 |
Family
ID=13579652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7555983A Granted JPS59198994A (ja) | 1983-04-28 | 1983-04-28 | 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 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59198994A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998020149A1 (fr) * | 1996-11-07 | 1998-05-14 | Ajinomoto Co., Inc. | PROCEDE DE PRODUCTION DE α-L-ASPARTYL-L-PHENYLALANINE OU DE α-L-ASPARTYL-L-PHENYLALANINATE METHYLIQUE |
| US7361458B2 (en) | 2003-01-24 | 2008-04-22 | Ajinomoto Co., Inc. | Method for producing α-L-aspartyl-L-phenylalanine-β-ester and method for producing α-L-aspartyl-L-phenylalanine-α-methyl ester |
-
1983
- 1983-04-28 JP JP7555983A patent/JPS59198994A/ja active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998020149A1 (fr) * | 1996-11-07 | 1998-05-14 | Ajinomoto Co., Inc. | PROCEDE DE PRODUCTION DE α-L-ASPARTYL-L-PHENYLALANINE OU DE α-L-ASPARTYL-L-PHENYLALANINATE METHYLIQUE |
| US7361458B2 (en) | 2003-01-24 | 2008-04-22 | Ajinomoto Co., Inc. | Method for producing α-L-aspartyl-L-phenylalanine-β-ester and method for producing α-L-aspartyl-L-phenylalanine-α-methyl ester |
| US7745172B2 (en) | 2003-01-24 | 2010-06-29 | Ajinomoto Co., Inc. | Method for producing α-L-aspartyl-L-phenylalanine-β-ester and method for producing α-L-aspartyl-L-phenylalanine-α-methyl ester |
| US8034584B2 (en) | 2003-01-24 | 2011-10-11 | Ajinomoto Co., Inc. | Method for producing α-L-aspartyl-L-phenylalanine-β-ester and method for producing α-L-aspartyl-L-phenylalanine-α-methyl ester |
| US8247193B2 (en) | 2003-01-24 | 2012-08-21 | Ajinomoto Co., Inc. | Method for producing α-L-aspartyl-L-phenylalanine-β-ester and method for producing α-L-aspartyl-L-phenylalanine-α-methyl ester |
| US8361748B2 (en) | 2003-01-24 | 2013-01-29 | Ajinomoto Co., Inc. | Method for producing α-L-aspartyl-L-phenylalanine-β-ester and method for producing α-L-aspartyl-L-phenylalanine-α-methyl ester |
| US8389240B2 (en) | 2003-01-24 | 2013-03-05 | Ajinomoto Co., Inc. | Method for producing α-L-aspartyl-L-phenylalanine-β-ester and method for producing α-L-aspartyl-L-phenylalanine-α-methyl ester |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0215196B2 (enrdf_load_stackoverflow) | 1990-04-11 |
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