KR880009122A - B아베르멕틴의 제조방법 및 이를 위한 배양물 - Google Patents
B아베르멕틴의 제조방법 및 이를 위한 배양물 Download PDFInfo
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- KR880009122A KR880009122A KR1019880000470A KR880000470A KR880009122A KR 880009122 A KR880009122 A KR 880009122A KR 1019880000470 A KR1019880000470 A KR 1019880000470A KR 880000470 A KR880000470 A KR 880000470A KR 880009122 A KR880009122 A KR 880009122A
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- 238000000034 method Methods 0.000 title claims 10
- 239000005660 Abamectin Substances 0.000 title claims 6
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 title claims 5
- -1 2-methylcyclopropyl Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 15
- 241001468227 Streptomyces avermitilis Species 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 230000000694 effects Effects 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 238000000855 fermentation Methods 0.000 claims 5
- 230000004151 fermentation Effects 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 101710088194 Dehydrogenase Proteins 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000004716 alpha keto acids Chemical class 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 230000001580 bacterial effect Effects 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 230000002950 deficient Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 235000015097 nutrients Nutrition 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 101710116650 FAD-dependent monooxygenase Proteins 0.000 claims 1
- 101710128228 O-methyltransferase Proteins 0.000 claims 1
- 241000187747 Streptomyces Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229950008167 abamectin Drugs 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000011081 inoculation Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000035699 permeability Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 229960005322 streptomycin Drugs 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
- C12P19/623—Avermectin; Milbemycin; Ivermectin; C-076
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Wood Science & Technology (AREA)
- Genetics & Genomics (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- Animal Behavior & Ethology (AREA)
- General Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Microbiology (AREA)
- Pest Control & Pesticides (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Fodder In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Enzymes And Modification Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- 측쇄 2-옥소 산 탈수소효소 활성 및 아베르멕틴 B 0-메틸 전이효소 활성이 결핍된 스트렙토마이세스 아베르미틸리스(Streptomyces avermitilis).
- 이의 투과성 세포가, 첨가된[14C-1]-2-옥소이소카프로산으로부터14CO2를 생성할 수 없음을 특징으로 하는, 측쇄 2-옥소 산 탈수소효소 활성 및 아베르멕틴 B0-메틸 전이효소 활성이 결핍된 스트렙토마이세스 아베르미틸리스.
- ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국종균협회, 기탁일 : 1988. 1. 9]와 동일한 특성을 갖는 스트렙토마이세스 아베르미틸리스.
- 스트렙토마이세스 아베르미틸리스 ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국종균협회, 기탁일 : 1988. 1. 9].
- 측쇄 2-옥소 산 탈수소효소 활성 및 아베르멕틴 B0-메틸 전이효소 활성이 결정된 스트렙토마이세스 아베르미틸리스 균주를 질소, 탄소 및 무기염의 동화, 가능한 공급원과 아베르멕틴 생합성에 이용가능한 화합물을 함유하는 수성 영양배지에서 호기성 발효시킴을 특징으로 하여, B아베르멕틴을 제조하는 방법.
- 제5항에 있어서, 에스. 아베르미틸리스가 ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국 종균협회, 기탁일 : 1988. 1. 9]와 동일한 특성을 갖는 방법.
- 제5항에 있어서, 화합물이 일반식(II-A)의 화합물 또는 발효공정 중에 일반식(II-A)의 화합물로 전환 가능한 화합물인 방법.R-COOH (II-A)상기식에서, R은 알파-측쇄그룹이고, -COOH그룹에 부착된 이의 탄소원자가 또한 수소 이외의 2개 이상의 다른 원자 또는 그룹에도 부착된다.
- 제7항에 있어서, R이 알파-측쇄 C3-C8알킬, 알케닐, 알키닐, 알콕시알킬 또는 알킬티오알킬그룹 : 알킬그룹이 알파-측쇄 C2-C5알킬그룹인 C5-C8사이클로 알킬알킬그룹; 메틸렌 또는 하나 이상의 C1-C4알킬그룹 또는 할로원자에 의해 임의 치환될 수 있는 C3-C8사이클로알킬 또는 C5-C8사이클로알케닐그룹 : 또는 포화 또는, 완전 또는 부분적 불포화되고 하나 이상의 C1-C4알킬그룹 또는 할로원자에 의해 임의 치환될 수 있는 3 내지 6원 산소 또는 황-함유 헤테로사이클릭 환인 화합물 또는 발효공정 중에 일반식(II-A)의 화합물로 전환가능한 화합물을 사용하는 방법.
- 제7항에 있어서, 기질 RCOOH로 전환가능한 화합물이 일반식(II-B)의 화합물인 방법.R-(CH2)n-Z (II-B)상기식에서, R은 상기 정의한 바와 같고; n은 0,2,4 또는 6이며; Z은 -CH2OH, -CHO, -COOR4, -CH2NH2또는 -CONHR5[여기서, R4는 H 또는(C1-6)알킬이고; R5는 수소, (C1-4)알킬, -CH(COOH)CH2COOH, -CH(COOH)(CH2)2COOH 또는 -CH(COOH)(CH2)2SCH3이다]이다.
- 제8항에 있어서, R이 사이클로부틸, 사이클로펜틸, 사이클로헥실, 사이클로헵틸, 2-메틸사이클로프로필, 3-사이클로헥세닐, 1-사이클로펜테닐, 1-사이클로헥세닐, 3-메틸사이클로헥실(시스/트랜스), 4-메틸렌사이클로헥실, 3-메틸사이클로부틸, 3-메틸렌사이클로부틸, 3-사이클로펜테닐, 1-사이클로프로필에틸, 3-플루오로사이클로부틸, 4,4-디플루오로사이클로헥실, 이소프로필, 2급-부틸, 2-펜틸, 2,3-디메틸프로필, 2-헥실, 2-펜트-4-에닐, 2-메틸티오에틸, S-2-펜틸, R-2-펜틸, 2-티에닐, 3-티에닐, 4-테트라히드로피라닐, 3-푸릴, 2-클로로티에닐, 3-테트라히드로티에닐, 4-메틸티오-2-부틸, 4-테트라히드로티오피라닐, 4-메톡시-2-부틸 또는 4-메틸티오-2-부틸인 방법.
- 제10항에 있어서, R이 일반식(II-A)의 카복실산으로부터 유도되는 방법.R-COOH (II-A)
- 제11항에 있어서, R이 사이클로펜틸, 사이클로헥실 또는 티에닐인 방법.
- 제10항에 있어서, R이 발효중에 R-COOH로 전환가능한 일반식(II-B)의 화합물로부터 유도되는 방법.R-(CH2)n-Z (II-B)상기식에서 R은 상기 정의한 바와 같고; n은 0,2,4 또는 6이며; Z은-CH2OH, -CHO, -COOR4, -CH2NH2또는 -CONHR5[여기서, R4는 (C1-6)알킬이고, R5는 수소, (C1-4)알킬, -CH(COOH)CH2COOH, -CH(C00H)(CH2)2COOH 또는 -CH(COOH)(CH2)2SCH3이다]이다.
- 제8항에 있어서, R이 알파-측쇄 C3-C8알킬그룹일 경우, 이소프로필 또는 (S)-2급-부틸이 아닌 방법.
- 제8항에 있어서, 에스.아베르미틸리스 균주가 에스.아베르미틸리스 ATCC 53692[한국기탁번호 : KFCC-10497, 기탁기관 : 한국종균협회, 기탁일 : 1988. 1. 9]인 방법.
- 탄소, 질소 및 무기염의 동화가능한 공급원을 함유하고, 일반식(II-A)의 산, 또는 에스.아베르미틸리스에 의해 상기 산으로 전환될 수 있는 화합물이 거의 없는 수성 영양배지 중에서 호기성 조건하에 발효시킬 경우에는, 거의 C-076 아베르멕틴을 생성하지 않지만, 일반식(II-A)의 산 또는, 에스.아베르미틸리스에 의해 상기 산으로 전환될 수 있는 화합물을 함유하는 배지 중에서 발효시킬 경우에는, 실질적으로 B아베르멕틴만을 생성할 수 있으며, 스트렙토마이TP스 아베르미틸리스 ATCC 53567[한국기탁번호 : KFCC-10493, 기탁기관 : 한국종균협회, 기탁번호 : 1988. 1. 9]을 돌연변이시킴을 특징으로 하는 방법으로 수득되는 스트렙토마이세스 속의 신규한 균주.R-COOH (II-A)상기식에서, R은 이소프로필 또는 (S)-2급-부틸이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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KR1019880000506A KR910002225B1 (ko) | 1987-01-23 | 1988-01-23 | 비-천연 데메틸아베르멕틴 및 이의 제조방법 |
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KR100415395B1 (ko) * | 2000-08-02 | 2004-01-16 | 한국생명공학연구원 | 에버멕틴 bc-5-o-메칠트랜스퍼라제의 유전자가 파괴된 스트렙토마이세스 에버미티리스 변이균주 및 그의 제조 방법 |
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