RU2226550C2 - Способ ферментативного получения непротеиногенных l-аминокислот - Google Patents
Способ ферментативного получения непротеиногенных l-аминокислот Download PDFInfo
- Publication number
- RU2226550C2 RU2226550C2 RU2001125710/13A RU2001125710A RU2226550C2 RU 2226550 C2 RU2226550 C2 RU 2226550C2 RU 2001125710/13 A RU2001125710/13 A RU 2001125710/13A RU 2001125710 A RU2001125710 A RU 2001125710A RU 2226550 C2 RU2226550 C2 RU 2226550C2
- Authority
- RU
- Russia
- Prior art keywords
- cysteine
- fermentation
- alanine
- group
- amino acids
- Prior art date
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/06—Alanine; Leucine; Isoleucine; Serine; Homoserine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/12—Methionine; Cysteine; Cystine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/848—Escherichia
- Y10S435/849—Escherichia coli
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Непротеиногенные L-аминокислоты получают путем непосредственной ферментации с использованием широко известного штамма микроорганизма, характеризующегося нарушенной регуляцией метаболизма цистеина, которую осуществляют согласно широко известному методу. Данный способ отличается от известного тем, что в процессе ферментации в среду для ферментации добавляют нуклеофильное соединение, которое представляет собой 1,2,3,4-тетразолил-L-аланин, или его производные, или S-гетероарил-L-цистеин. Использование такого нуклеофильного соединения в определенных количествах приводит к продуцированию непротеиногенных L-аминокислот штаммом микроорганизма. 2 с. и 16 з.п. ф-лы.
Description
Текст описания в факсимильном виде (см. графическую часть).
Claims (18)
1. Способ получения непротеиногенных L-аминокислот, предусматривающий ферментацию с использованием штамма микроорганизма с нарушенной регуляцией метаболизма цистеина и выделение L-аминокислот, отличающийся тем, что в процессе ферментации в среду для ферментации добавляют нуклеофильное соединение в количестве 10 - 1000 ммолей на 1 л начального объема ферментационной среды после начала ферментации, что приводит к продуцированию непротеиногенных L-аминокислот.
3. Способ по п.1 или 2, отличающийся тем, что нуклеофильное соединение выбирают из группы соединений, включающей тиол общей формулы (1):
где R1 обозначает одновалентный замещенный или незамещенный алкил, алкоксигруппу, арил или гетероарил, имеющий максимум 15 атомов углерода; азол общей формулы (2) или (3):
а также его сложные и простые эфиры или соли,
где Х и Y имеют одинаковые или различные значения и обозначают CR4 или N, где R4 обозначает –Н, –СООН, –ОН, –NH2, –NO , –SH, –SO , –F, –Cl, –Br, –I, С1-С5алкилкарбонил- или R1, где R1 имеет значения, указанные для формулы (1), при этом R2 и R3 имеют одинаковые или различные значения и обозначают R4, или С1 и С2 в формуле (3) вместо заместителей R2 и R3 присоединены к кольцу с помощью мостика [–CR5R6–]а, где а равно 1, 2, 3 или 4, при этом R5 и R6 имеют одинаковые или различные значения и обозначают R4, и одна или несколько групп [–CR5R6–], которые не являются соседними, могут быть замещены атомом кислорода, серы или при необходимости иминофрагментом, замещенным С1-С5 алкилом, и две соседние группы [–CR5R6–] могут быть заменены группой [–CR5=R6–] или группой [–CR5=N–], - изоксазолинон общей формулы (4) или (5):
а также его сложные и простые эфиры или соли,
где Х, R1, R2 и R3 имеют указанные выше значения, С1 и С2 в формуле (5) вместо заместителей R2 и R3 могут быть присоединены к кольцу с помощью указанного для формулы (3) мостика.
4. Способ по любому из пп.1-3, отличающийся тем, что в способе по изобретению применяют штамм микроорганизмов, выбранный из группы, включающей следующие штаммы: штаммы с модифицированными cysЕ-аллелями; штаммы, содержащие гены экспорта; штаммы с измененной CysB-активностью; штаммы, которые получают с помощью методов неспецифического мутагенеза в сочетании с методами скрининга с целью сверхпроизводства цистеина или уменьшения разложения цистеина.
5. Способ по любому из пп.1-4, отличающийся тем, что в качестве штамма микроорганизмов применяют штамм Escherichia coli.
6. Способ по пп.1, 4 или 5, отличающийся тем, что культивирование штамма микроорганизма в ферментере осуществляют непрерывно, периодически (культивирование партий) либо с использованием периодического процесса с подпиткой.
7. Способ по любому из пп.1-6, отличающийся тем, что источник углерода и нуклеофильное соединение добавляют непрерывно в процессе ферментации.
8. Способ по любому из пп.1-7, отличающийся тем, что добавление нуклеофильного соединения начинают через 6-8 ч после начала ферментации и продолжают до окончания ферментации.
9. Способ по любому из пп.1-8, отличающийся тем, что количество добавляемого нуклеофильного соединения составляет 10 - 1000 ммолей на 1 л начального объема среды для ферментации.
10. Способ по любому из пп.1-9, отличающийся тем, что в качестве источника углерода для ферментации применяют сахар, многоатомный спирт, дающий при окислении моносахарид, или органические кислоты.
11. Способ по п.10, отличающийся тем, что источники углерода вносят таким образом, что содержание глюкозы в ферментере составляет 0,1-50 г/л.
12. Способ по любому из пп.1-11, отличающийся тем, что в качестве источника азота применяют аммиак, соли аммония или протеиновые гидролизаты.
13. Способ по любому из пп.1-12, отличающийся тем, что значение рН среды для ферментации составляет 4-10 и температура инкубации составляет 15-45°С.
14. Способ по любому из пп.1-13, отличающийся тем, что его осуществляют в аэробных условиях для роста.
15. Способ по любому из пп.1-14, отличающийся тем, что после удаления биомассы из среды для ферментации путем фильтрации или центрифугирования непротеиногенные L-аминокислоты выделяют из надосадочной жидкости культуры с помощью экстракции, адсорбции, ионообменной хроматографии, осаждения или кристаллизации.
16. Способ по любому из пп.1-15, отличающийся тем, что непротеиногенная L-аминокислота представляет собой аминокислоту общей формулы (6), имеющую L-конфигурацию:
где Z обозначает одновалентный радикал, выбранный из группы, включающей радикалы формул (7)-(13)
а также их сложные эфиры, простые эфиры или соли,
где R1, R2, R3, R4, Х и Y имеют значения, указанные для формул (1) - (5).
17. Соединение, выбранное из группы, включающей 1,2,3,4-тетразолил-L-аланин и его производные, 1,2,3-триазолил-L-аланин и его производные и S-гетероарил-L-цистеин.
18. Соединение по п.17, выбранное из группы, включающей 1,2,3,4-тетразол-1-ил-L-аланин, 1,2,3,4-тетразол-2-ил-L-аланин, 1,2,3-бензотриазол-1-ил-L-аланин, 1,2,3-бензотриазол-2-ил-L-аланин, 5-карбокси-1,2,3-бензотриазол-1-ил-L-аланин, 5-карбокси-1,2,3-бензотриазол-2-ил-L-аланин, 1,2,4-триазол-3-ил-L-цистеин, тиазол-2-ил-L-цистеин, имидазол-2-ил-L-цистеин, тиен-2-ил-L-цистеин, пиридин-2-ил-L-цистеин, пиримидин-2-ил-L-цистеин, бензотиазол-2-ил-L-цистеин и бензоксазол-2-ил-L-цистеин.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10046934.5 | 2000-09-21 | ||
DE10046934A DE10046934A1 (de) | 2000-09-21 | 2000-09-21 | Verfahren zur fermentativen Herstellung von nicht-proteinogenen L-Aminosäuren |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2001125710A RU2001125710A (ru) | 2003-07-27 |
RU2226550C2 true RU2226550C2 (ru) | 2004-04-10 |
Family
ID=7657192
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2001125710/13A RU2226550C2 (ru) | 2000-09-21 | 2001-09-20 | Способ ферментативного получения непротеиногенных l-аминокислот |
Country Status (19)
Country | Link |
---|---|
US (3) | US6756216B2 (ru) |
EP (1) | EP1191106B1 (ru) |
JP (1) | JP4240864B2 (ru) |
KR (1) | KR100475985B1 (ru) |
CN (1) | CN1250735C (ru) |
AT (1) | ATE265541T1 (ru) |
AU (1) | AU758402B2 (ru) |
BR (1) | BR0104188A (ru) |
CA (1) | CA2357469A1 (ru) |
DE (2) | DE10046934A1 (ru) |
DK (1) | DK1191106T3 (ru) |
ES (1) | ES2220639T3 (ru) |
HU (1) | HUP0103764A2 (ru) |
MX (1) | MXPA01009508A (ru) |
PL (1) | PL349759A1 (ru) |
RU (1) | RU2226550C2 (ru) |
SK (1) | SK286163B6 (ru) |
TW (1) | TWI258507B (ru) |
ZA (1) | ZA200107763B (ru) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6579705B2 (en) | 2001-04-04 | 2003-06-17 | Consortium Fur Elektrochemische Industrie Gmbh | Process for preparing non-proteinogenic L-amino acids |
WO2004041274A1 (en) * | 2002-11-05 | 2004-05-21 | Arena Pharmaceuticals, Inc. | Benzotriazoles and methods of prophylaxis or treatment of metabolic-related disorders thereof |
DE10331291A1 (de) * | 2003-07-10 | 2005-02-17 | Consortium für elektrochemische Industrie GmbH | Varianten der 3-Phosphoglyceratdehydrogenase mit reduzierter Hemmung durch L-Serin und dafür codierende Gene |
CA2799154A1 (en) | 2010-05-12 | 2011-11-17 | Abbvie Inc. | Indazole inhibitors of kinase |
US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
CN103614428B (zh) * | 2013-06-26 | 2017-08-04 | 山东鲁抗医药股份有限公司 | 一种发酵生产l‑色氨酸的方法 |
DE102013219016A1 (de) | 2013-09-20 | 2015-03-26 | Wacker Chemie Ag | Verfahren zur fermentativen Herstellung von Gamma-Glutamylcystein und Derivaten dieses Dipeptids |
US10773049B2 (en) | 2016-06-21 | 2020-09-15 | Ventec Life Systems, Inc. | Cough-assist systems with humidifier bypass |
WO2023094011A1 (de) | 2021-11-29 | 2023-06-01 | Wacker Chemie Ag | Verfahren zur herstellung von l-cysteinsäure |
KR20240091231A (ko) | 2021-11-29 | 2024-06-21 | 와커 헤미 아게 | 타우린의 생산방법 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE23331T1 (de) * | 1979-11-30 | 1986-11-15 | Fujisawa Pharmaceutical Co | 5-thio-tetrazolverbindungen und ihre herstellung. |
EP0029998B1 (en) * | 1979-11-30 | 1985-03-06 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds, processes for their preparation and pharmaceutical compositions containing them |
US4420477A (en) * | 1979-11-30 | 1983-12-13 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
JPS57120421A (en) * | 1981-01-16 | 1982-07-27 | Tokai Kasei Kogyo Kk | Manufacture of foamed product lined with core material |
CA1292200C (en) * | 1987-04-24 | 1991-11-19 | Tatsuo Miyazawa | Method for producing protein containing nonprotein amino acids |
KR0130196B1 (ko) * | 1990-02-15 | 1998-04-03 | 도바 다다스 | 염기성 아미노산과 산성 아미노산의 동시 발효법 |
US5646167A (en) * | 1993-01-06 | 1997-07-08 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamix acids |
DE19539952A1 (de) * | 1995-10-26 | 1997-04-30 | Consortium Elektrochem Ind | Verfahren zur Herstellung von O-Acetylserin, L-Cystein und L-Cystein-verwandten Produkten |
US5728555A (en) * | 1996-09-30 | 1998-03-17 | Monsanto Company | Preparation of d-amino acids by direct fermentative means |
JP4088982B2 (ja) * | 1996-10-15 | 2008-05-21 | 味の素株式会社 | 発酵法によるl−アミノ酸の製造法 |
DE19726083A1 (de) | 1997-06-19 | 1998-12-24 | Consortium Elektrochem Ind | Mikroorganismen und Verfahren zur fermentativen Herstellung von L-Cystein, L-Cystin, N-Acetyl-Serin oder Thiazolidinderivaten |
JP3966583B2 (ja) * | 1997-06-23 | 2007-08-29 | 協和醗酵工業株式会社 | 発酵法によるl−アミノ酸の製造法 |
JPH11106398A (ja) * | 1997-10-01 | 1999-04-20 | Morinaga Milk Ind Co Ltd | ペプチド誘導体および抗真菌剤 |
US6191168B1 (en) * | 1998-06-02 | 2001-02-20 | Edward Rubenstein | Methods for the use of nonprotein amino acids as therapeutic agents |
DE19849625A1 (de) * | 1998-10-28 | 2000-05-04 | Degussa | Verfahren zur fermentativen Herstellung von L-Aminosäuren |
DE19949579C1 (de) * | 1999-10-14 | 2000-11-16 | Consortium Elektrochem Ind | Verfahren zur fermentativen Herstellung von L-Cystein oder L-Cystein-Derivaten |
-
2000
- 2000-09-21 DE DE10046934A patent/DE10046934A1/de not_active Withdrawn
-
2001
- 2001-09-06 ES ES01120750T patent/ES2220639T3/es not_active Expired - Lifetime
- 2001-09-06 AT AT01120750T patent/ATE265541T1/de active
- 2001-09-06 DK DK01120750T patent/DK1191106T3/da active
- 2001-09-06 DE DE50102109T patent/DE50102109D1/de not_active Expired - Lifetime
- 2001-09-06 EP EP01120750A patent/EP1191106B1/de not_active Expired - Lifetime
- 2001-09-18 JP JP2001283510A patent/JP4240864B2/ja not_active Expired - Fee Related
- 2001-09-19 PL PL01349759A patent/PL349759A1/xx unknown
- 2001-09-19 CA CA002357469A patent/CA2357469A1/en not_active Abandoned
- 2001-09-19 KR KR10-2001-0057922A patent/KR100475985B1/ko not_active IP Right Cessation
- 2001-09-20 ZA ZA200107763A patent/ZA200107763B/xx unknown
- 2001-09-20 AU AU75562/01A patent/AU758402B2/en not_active Ceased
- 2001-09-20 MX MXPA01009508A patent/MXPA01009508A/es active IP Right Grant
- 2001-09-20 RU RU2001125710/13A patent/RU2226550C2/ru not_active IP Right Cessation
- 2001-09-20 HU HU0103764A patent/HUP0103764A2/hu unknown
- 2001-09-21 TW TW090123402A patent/TWI258507B/zh not_active IP Right Cessation
- 2001-09-21 SK SK1348-2001A patent/SK286163B6/sk not_active IP Right Cessation
- 2001-09-21 BR BR0104188-6A patent/BR0104188A/pt not_active IP Right Cessation
- 2001-09-21 CN CNB011422254A patent/CN1250735C/zh not_active Expired - Fee Related
- 2001-09-21 US US09/957,961 patent/US6756216B2/en not_active Expired - Lifetime
-
2004
- 2004-04-28 US US10/833,569 patent/US6939967B2/en not_active Expired - Lifetime
-
2005
- 2005-05-17 US US11/130,955 patent/US7015331B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
SK13482001A3 (sk) | 2002-04-04 |
CN1344801A (zh) | 2002-04-17 |
EP1191106B1 (de) | 2004-04-28 |
DK1191106T3 (da) | 2004-08-16 |
ATE265541T1 (de) | 2004-05-15 |
BR0104188A (pt) | 2002-05-07 |
DE10046934A1 (de) | 2002-04-18 |
US7015331B2 (en) | 2006-03-21 |
SK286163B6 (sk) | 2008-04-07 |
US6939967B2 (en) | 2005-09-06 |
HUP0103764A2 (en) | 2006-01-30 |
PL349759A1 (en) | 2002-03-25 |
CA2357469A1 (en) | 2002-03-21 |
AU758402B2 (en) | 2003-03-20 |
DE50102109D1 (de) | 2004-06-03 |
US20040197879A1 (en) | 2004-10-07 |
JP4240864B2 (ja) | 2009-03-18 |
KR20020023130A (ko) | 2002-03-28 |
TWI258507B (en) | 2006-07-21 |
EP1191106A1 (de) | 2002-03-27 |
ES2220639T3 (es) | 2004-12-16 |
MXPA01009508A (es) | 2003-05-19 |
AU7556201A (en) | 2002-03-28 |
CN1250735C (zh) | 2006-04-12 |
US6756216B2 (en) | 2004-06-29 |
US20050222426A1 (en) | 2005-10-06 |
ZA200107763B (en) | 2002-05-16 |
JP2002165598A (ja) | 2002-06-11 |
US20020039767A1 (en) | 2002-04-04 |
KR100475985B1 (ko) | 2005-03-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
RU2226550C2 (ru) | Способ ферментативного получения непротеиногенных l-аминокислот | |
JP2676568B2 (ja) | R(−)−マンデル酸およびその誘導体の製造法 | |
EP0175312B1 (en) | Process for preparing optically active hydantoins | |
RU2001125710A (ru) | Способ ферментативного получения непротеиногенных L-аминокислот | |
US5068187A (en) | Process for producing D-α-amino acids | |
CN109321487B (zh) | 假单胞菌zjut126及在生产L-草铵膦中的应用 | |
JPS61242589A (ja) | L−含硫アミノ酸の製造方法 | |
EP0309310B1 (fr) | Nouveau système enzymatique, son procédé de préparation et son application notamment dans la préparation de la D-parahydroxyphénylglycine | |
JP2696127B2 (ja) | 光学活性な2―ヒドロキシカルボン酸の製造法 | |
JPH01320991A (ja) | D−ホモフエニルアラニン類の製造方法 | |
SK282099B6 (sk) | Mikroorganizmy a bezbunkové enzýmy zúžitkujúce n-chránený derivát prolínu a spôsob jeho výroby | |
JP2864277B2 (ja) | 光学活性アミノ酸類の製造方法 | |
KR950005925B1 (ko) | D-(-)-타르타르산의 제조법 | |
JP3596919B2 (ja) | 高純度光学活性化合物の製造法 | |
JP2716477B2 (ja) | S‐カルボキシメチル‐l‐システインの製造方法 | |
JPH0611232B2 (ja) | L−含硫アミノ酸の製造方法 | |
JP2674078B2 (ja) | D−α−アミノ酸の製造法 | |
JPS60184392A (ja) | D−α−アミノ酸の製造方法 | |
EP1311700B1 (en) | Production process of l-phenylalanine derivatives by microorganisms | |
JP2002034593A (ja) | 光学活性α−アミノ酸の製造方法 | |
SU1124029A1 (ru) | Способ получени питательной среды дл производства биомассы @ @ | |
JP2002509441A (ja) | D−特異的アミノアシラーゼを使用するエナンチオマー的に純粋な環状α−アミノ酸およびそのN−保護誘導体の製造方法 | |
EP0187525A2 (en) | Process for producing L-serine | |
JP2007319053A (ja) | 光学活性なアミノ酸誘導体の製造方法 | |
JPH04252189A (ja) | ベンゼンジカルボン酸モノエステルまたはその誘導体の製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PC4A | Invention patent assignment |
Effective date: 20070904 |
|
RH4A | Copy of patent granted that was duplicated for the russian federation |
Effective date: 20070820 |
|
MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20080921 |