JPS5452033A - Preparation of selenoamino acid - Google Patents
Preparation of selenoamino acidInfo
- Publication number
- JPS5452033A JPS5452033A JP11766477A JP11766477A JPS5452033A JP S5452033 A JPS5452033 A JP S5452033A JP 11766477 A JP11766477 A JP 11766477A JP 11766477 A JP11766477 A JP 11766477A JP S5452033 A JPS5452033 A JP S5452033A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- selenol
- amino acid
- methioninase
- rso
- 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
- 239000002253 acid Substances 0.000 title abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 3
- 108010043135 L-methionine gamma-lyase Proteins 0.000 abstract 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract 2
- 239000003125 aqueous solvent Substances 0.000 abstract 2
- 150000003958 selenols Chemical class 0.000 abstract 2
- YWBHROUQJYHSOR-UHFFFAOYSA-N $l^{1}-selanylbenzene Chemical compound [Se]C1=CC=CC=C1 YWBHROUQJYHSOR-UHFFFAOYSA-N 0.000 abstract 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-N 2-oxobutanoic acid Chemical compound CCC(=O)C(O)=O TYEYBOSBBBHJIV-UHFFFAOYSA-N 0.000 abstract 1
- JTWUZULPZAALRN-UHFFFAOYSA-N 3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde;phosphoric acid Chemical compound OP(O)(O)=O.CC1=NC=C(CO)C(C=O)=C1O JTWUZULPZAALRN-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- 229930195722 L-methionine Natural products 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229960004452 methionine Drugs 0.000 abstract 1
- 229940107700 pyruvic acid Drugs 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- -1 γ-phenylseleno-α-aminobutyric acid Chemical compound 0.000 abstract 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To prepare a physiologically active title compound having a chemical structure similar to a sulfur-containing amino acid, industrially, by reacting a specific β- or γ-substituted amino acid with selenol in the presence of an enzyme methioninase as cadtalyst, in an aqueous medium.
CONSTITUTION: A selenoamino acid II (e.g. γ-phenylseleno-α-aminobutyric acid) is prepared by reacting a β- or γ-substituted amino acid I [X is halogen, RO-, RS-, RSO-, RSO2- (R is H, lower alkyl); n is 1,2] (e.g. L-methionine, which is decomposed into XH, ammonium ion, and pyruvic acid or α-ketobutyric acid by contacting with methioninase in an aqueous solvent) with selenol of formula Y-SeH (Y is an orgainc residue) (e.g. phenyl selenol) in the presence of methionniase in an aqueous solvent pref. containing pyridoxal phosphoric acid
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11766477A JPS5452033A (en) | 1977-09-29 | 1977-09-29 | Preparation of selenoamino acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11766477A JPS5452033A (en) | 1977-09-29 | 1977-09-29 | Preparation of selenoamino acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5452033A true JPS5452033A (en) | 1979-04-24 |
| JPS578717B2 JPS578717B2 (en) | 1982-02-17 |
Family
ID=14717221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11766477A Granted JPS5452033A (en) | 1977-09-29 | 1977-09-29 | Preparation of selenoamino acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5452033A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU687768B2 (en) * | 1992-11-19 | 1998-03-05 | Anticancer, Inc. | Use of methioninase as an antitumor agent in anti-methionine chemotherapy |
| JP2013522213A (en) * | 2010-03-09 | 2013-06-13 | ノーバス・インターナショナル・インコーポレイテッド | Production of methionine or selenomethionine from homoserine via lactone intermediate |
| RU2669771C2 (en) * | 2015-12-11 | 2018-10-16 | Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Профессионального Образования "Пензенский Государственный Университет Архитектуры И Строительства" | 3,3-diseleno-bis-2-aminobutyric acid and method for preparation thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57203514U (en) * | 1981-06-15 | 1982-12-24 |
-
1977
- 1977-09-29 JP JP11766477A patent/JPS5452033A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU687768B2 (en) * | 1992-11-19 | 1998-03-05 | Anticancer, Inc. | Use of methioninase as an antitumor agent in anti-methionine chemotherapy |
| JP2013522213A (en) * | 2010-03-09 | 2013-06-13 | ノーバス・インターナショナル・インコーポレイテッド | Production of methionine or selenomethionine from homoserine via lactone intermediate |
| RU2669771C2 (en) * | 2015-12-11 | 2018-10-16 | Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Профессионального Образования "Пензенский Государственный Университет Архитектуры И Строительства" | 3,3-diseleno-bis-2-aminobutyric acid and method for preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS578717B2 (en) | 1982-02-17 |
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