JPH0144316B2 - - Google Patents

Info

Publication number: JPH0144316B2
Authority: JP; Japan
Prior art keywords: compound; bacterial cells; solution; acid; cysteine
Prior art date: 1986-05-22
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.): Expired

Application number

JP11822786A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6225995A (ja

Inventor

Hidehiko Kumagai

Tatsurokuro Tochikura

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ajinomoto Co Inc

Original Assignee

Ajinomoto Co Inc

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.)

1986-05-22

Filing date

1986-05-22

Publication date

1989-09-27

1986-05-22 Application filed by Ajinomoto Co Inc filed Critical Ajinomoto Co Inc

1986-05-22 Priority to JP11822786A priority Critical patent/JPS6225995A/ja

1987-02-03 Publication of JPS6225995A publication Critical patent/JPS6225995A/ja

1989-09-27 Publication of JPH0144316B2 publication Critical patent/JPH0144316B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 27
229940126062 Compound A Drugs 0.000 claims description 14
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 14
244000005700 microbiome Species 0.000 claims description 10
WHUUTDBJXJRKMK-VKHMYHEASA-N L-Glutamic acid Natural products OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 9
UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims description 6
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 6
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 6
229960002989 glutamic acid Drugs 0.000 claims description 5
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
QWCKQJZIFLGMSD-VKHMYHEASA-N L-alpha-aminobutyric acid Chemical compound CC[C@H](N)C(O)=O QWCKQJZIFLGMSD-VKHMYHEASA-N 0.000 claims description 4
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 4
RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims description 4
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 4
UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims description 3
PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical group CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 claims description 3
241000588698 Erwinia Species 0.000 claims description 3
239000004395 L-leucine Substances 0.000 claims description 3
235000019454 L-leucine Nutrition 0.000 claims description 3
239000004473 Threonine Substances 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
229960003136 leucine Drugs 0.000 claims description 3
229960002898 threonine Drugs 0.000 claims description 3
241000193830 Bacillus <bacterium> Species 0.000 claims description 2
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 2
241000588914 Enterobacter Species 0.000 claims description 2
241000588722 Escherichia Species 0.000 claims description 2
239000004471 Glycine Substances 0.000 claims description 2
PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 2
SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims description 2
QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 2
FFFHZYDWPBMWHY-UHFFFAOYSA-N L-Homocysteine Natural products OC(=O)C(N)CCS FFFHZYDWPBMWHY-UHFFFAOYSA-N 0.000 claims description 2
FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 claims description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims description 2
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 2
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
229930195722 L-methionine Natural products 0.000 claims description 2
SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims description 2
241000192041 Micrococcus Species 0.000 claims description 2
241000588769 Proteus <enterobacteria> Species 0.000 claims description 2
241000589516 Pseudomonas Species 0.000 claims description 2
229960003767 alanine Drugs 0.000 claims description 2
150000003862 amino acid derivatives Chemical class 0.000 claims description 2
229960001230 asparagine Drugs 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229960002173 citrulline Drugs 0.000 claims description 2
229960002449 glycine Drugs 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
229960004452 methionine Drugs 0.000 claims description 2
229960001153 serine Drugs 0.000 claims description 2
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims description 2
229960004295 valine Drugs 0.000 claims description 2
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 2
WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims 2
229930182847 D-glutamic acid Natural products 0.000 claims 1
HWXBTNAVRSUOJR-UHFFFAOYSA-N alpha-hydroxyglutaric acid Natural products OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 claims 1
229940009533 alpha-ketoglutaric acid Drugs 0.000 claims 1
239000000243 solution Substances 0.000 description 33
210000004027 cell Anatomy 0.000 description 23
230000001580 bacterial effect Effects 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 18
108090000790 Enzymes Proteins 0.000 description 13
102000004190 Enzymes Human genes 0.000 description 13
229940088598 enzyme Drugs 0.000 description 12
238000000034 method Methods 0.000 description 8
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 7
239000008363 phosphate buffer Substances 0.000 description 5
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 3
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 3
239000004201 L-cysteine Substances 0.000 description 3
102000007327 Protamines Human genes 0.000 description 3
108010007568 Protamines Proteins 0.000 description 3
241000588770 Proteus mirabilis Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
239000000872 buffer Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
235000018417 cysteine Nutrition 0.000 description 3
239000008103 glucose Substances 0.000 description 3
229910052588 hydroxylapatite Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 3
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
235000013878 L-cysteine Nutrition 0.000 description 2
RITKHVBHSGLULN-WHFBIAKZSA-N L-gamma-glutamyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(O)=O RITKHVBHSGLULN-WHFBIAKZSA-N 0.000 description 2
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
239000001888 Peptone Substances 0.000 description 2
108010080698 Peptones Proteins 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000012258 culturing Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
235000019319 peptone Nutrition 0.000 description 2
229940048914 protamine Drugs 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
238000011282 treatment Methods 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
238000005199 ultracentrifugation Methods 0.000 description 2
QWCKQJZIFLGMSD-UHFFFAOYSA-N 2-Aminobutanoic acid Natural products CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 1
241000589155 Agrobacterium tumefaciens Species 0.000 description 1
241000588986 Alcaligenes Species 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
244000063299 Bacillus subtilis Species 0.000 description 1
241000193764 Brevibacillus brevis Species 0.000 description 1
YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
241000186145 Corynebacterium ammoniagenes Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
229930064664 L-arginine Natural products 0.000 description 1
235000014852 L-arginine Nutrition 0.000 description 1
229930182844 L-isoleucine Natural products 0.000 description 1
229930182821 L-proline Natural products 0.000 description 1
241001153358 Micrococcus luteus NCTC 2665 Species 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
241000203720 Pimelobacter simplex Species 0.000 description 1
101710093543 Probable non-specific lipid-transfer protein Proteins 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000158504 Rhodococcus hoagii Species 0.000 description 1
239000012506 Sephacryl® Substances 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229960002303 citric acid monohydrate Drugs 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
108010068906 gamma-glutamylcysteine Proteins 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960002885 histidine Drugs 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
229960000274 lysozyme Drugs 0.000 description 1
235000010335 lysozyme Nutrition 0.000 description 1
239000004325 lysozyme Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
229960002429 proline Drugs 0.000 description 1
229950008679 protamine sulfate Drugs 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
238000011002 quantification Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000010257 thawing Methods 0.000 description 1
235000019157 thiamine Nutrition 0.000 description 1
KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
229960003495 thiamine Drugs 0.000 description 1
239000011721 thiamine Substances 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

JP11822786A 1986-05-22 1986-05-22 アミノ酸誘導体の製造法 Granted JPS6225995A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP11822786A JPS6225995A (ja)	1986-05-22	1986-05-22	アミノ酸誘導体の製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP11822786A JPS6225995A (ja)	1986-05-22	1986-05-22	アミノ酸誘導体の製造法

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP13329479A Division JPS5658495A (en)	1979-10-16	1979-10-16	Preparation of amino acid derivative

Publications (2)

Publication Number	Publication Date
JPS6225995A JPS6225995A (ja)	1987-02-03
JPH0144316B2 true JPH0144316B2 (es)	1989-09-27

Family

ID=14731367

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11822786A Granted JPS6225995A (ja)	1986-05-22	1986-05-22	アミノ酸誘導体の製造法

Country Status (1)

Country	Link
JP (1)	JPS6225995A (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MX2011010407A (es)	2009-04-01	2012-01-20	Ajinomoto Kk	Uso de peptico para impartir gusto corporal.
WO2014017485A1 (ja) *	2012-07-25	2014-01-30	味の素株式会社	果汁含有飲食品

1986
- 1986-05-22 JP JP11822786A patent/JPS6225995A/ja active Granted

Also Published As

Publication number	Publication date
JPS6225995A (ja)	1987-02-03

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JPH0144316B2 (es)	1989-09-27
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Triantafillou et al.	1988	Purification and properties of a membrane-bound L-asparaginase of Tetrahymena pyriformis
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JPS5854797B2 (ja)	1983-12-06	γ−Ｌ−グルタミル−４−ヒドロキシアニリドの製造法
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JPH0424994B2 (es)	1992-04-28