SI20120A - Nova karbonil reduktaza, gen, ki omenjeno kodira in postopek za uporabo take reduktaze in gena - Google Patents

Nova karbonil reduktaza, gen, ki omenjeno kodira in postopek za uporabo take reduktaze in gena Download PDF

Info

Publication number: SI20120A
Authority: SI; Slovenia
Prior art keywords: enzyme; ethyl; plasmid; hydrogen; optically active
Prior art date: 1997-02-07

Application number

SI9720093A

Other languages

English (en)

Slovenian (sl)

Inventor

Yasohara Yoshihiko

Kizaki Noriyuki

Hasegawa Junzo

Wada Masaru

Shimizu Sakayu

Kataoka Michihiko

Yamamoto Kazuhiko

Kawabata Hiroshi

Kita Keiko

Original Assignee

Kaneka Corporation

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.)

1997-02-07

Filing date

1997-09-01

Publication date

2000-06-30

1997-09-01 Application filed by Kaneka Corporation filed Critical Kaneka Corporation

2000-06-30 Publication of SI20120A publication Critical patent/SI20120A/sl

Links

238000000034 method Methods 0.000 title claims abstract description 59
102000005751 Alcohol Oxidoreductases Human genes 0.000 title claims description 12
108010031132 Alcohol Oxidoreductases Proteins 0.000 title claims description 12
108090000623 proteins and genes Proteins 0.000 title description 14
108090000790 Enzymes Proteins 0.000 claims abstract description 175
102000004190 Enzymes Human genes 0.000 claims abstract description 172
239000013612 plasmid Substances 0.000 claims abstract description 81
230000000694 effects Effects 0.000 claims abstract description 59
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 38
230000008569 process Effects 0.000 claims abstract description 28
150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 18
108010050375 Glucose 1-Dehydrogenase Proteins 0.000 claims description 39
239000005515 coenzyme Substances 0.000 claims description 31
239000000758 substrate Substances 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
241000588724 Escherichia coli Species 0.000 claims description 27
OHLRLMWUFVDREV-UHFFFAOYSA-N ethyl 4-chloro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CCl OHLRLMWUFVDREV-UHFFFAOYSA-N 0.000 claims description 27
150000001413 amino acids Chemical class 0.000 claims description 26
241001131785 Escherichia coli HB101 Species 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 22
ZAJNMXDBJKCCAT-YFKPBYRVSA-N ethyl (3s)-4-chloro-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@H](O)CCl ZAJNMXDBJKCCAT-YFKPBYRVSA-N 0.000 claims description 22
230000009467 reduction Effects 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 17
-1 mercury ions Chemical class 0.000 claims description 17
239000000126 substance Substances 0.000 claims description 17
241000222292 [Candida] magnoliae Species 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 14
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 11
125000001475 halogen functional group Chemical group 0.000 claims description 11
REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
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230000001419 dependent effect Effects 0.000 claims description 7
238000003306 harvesting Methods 0.000 claims description 7
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 6
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
238000002523 gelfiltration Methods 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
HFLMYYLFSNEOOT-UHFFFAOYSA-N methyl 4-chloro-3-oxobutanoate Chemical group COC(=O)CC(=O)CCl HFLMYYLFSNEOOT-UHFFFAOYSA-N 0.000 claims description 6
ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 5
HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 5
238000001962 electrophoresis Methods 0.000 claims description 5
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 5
229960001285 quercetin Drugs 0.000 claims description 5
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
ATPFRGQBOVFFQM-WJIDAKASSA-N [(1s,3r,7r,8r,8as)-3-(hydroxymethyl)-8-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate Chemical compound C([C@@H]1[C@H](C)C=CC2=C[C@H](CO)C[C@@H]([C@@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 ATPFRGQBOVFFQM-WJIDAKASSA-N 0.000 claims description 4
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FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
CZRWOPRGDPUSDE-UHFFFAOYSA-N methyl 4-bromo-3-oxobutanoate Chemical compound COC(=O)CC(=O)CBr CZRWOPRGDPUSDE-UHFFFAOYSA-N 0.000 claims description 2
125000003275 alpha amino acid group Chemical group 0.000 claims 4
125000005843 halogen group Chemical group 0.000 claims 2
ACFIXJIJDZMPPO-NNYOXOHSSA-N NADPH Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](OP(O)(O)=O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 ACFIXJIJDZMPPO-NNYOXOHSSA-N 0.000 claims 1
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XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 31
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Classifications

- 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
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- 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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
- 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
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/0004—Oxidoreductases (1.)
- C12N9/0006—Oxidoreductases (1.) acting on CH-OH groups as donors (1.1)
- 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions

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Health & Medical Sciences (AREA)
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Biochemistry (AREA)
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General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Biomedical Technology (AREA)
Analytical Chemistry (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Enzymes And Modification Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)

SI9720093A 1997-02-07 1997-09-01 Nova karbonil reduktaza, gen, ki omenjeno kodira in postopek za uporabo take reduktaze in gena SI20120A (sl)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2566797		1997-02-07
JP11305297		1997-04-30
PCT/JP1997/003051 WO1998035025A1 (en)	1997-02-07	1997-09-01	Novel carbonyl reductase, gene that encodes the same, and method of utilizing these

Publications (1)

Publication Number	Publication Date
SI20120A true SI20120A (sl)	2000-06-30

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Country Status (14)

Country	Link
US (2)	US6218156B1 (cs)
EP (1)	EP0967271B1 (cs)
JP (1)	JP4012257B2 (cs)
KR (1)	KR100506134B1 (cs)
AT (1)	ATE280218T1 (cs)
AU (1)	AU4032997A (cs)
CA (1)	CA2280502A1 (cs)
CZ (1)	CZ298236B6 (cs)
DE (1)	DE69731317T2 (cs)
ES (1)	ES2235246T3 (cs)
IL (2)	IL131241A0 (cs)
SI (1)	SI20120A (cs)
SK (1)	SK105699A3 (cs)
WO (1)	WO1998035025A1 (cs)

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KR20010103017A (ko) *	1999-02-19	2001-11-17	플레믹 크리스티안	글루코스 데히드로게나제 융합 단백질 및 발현계에서의그의 용도
TWI275645B (en) *	2000-02-16	2007-03-11	Daicel Chemical Industries Ltd.	(R)-2-octanol dehydrogenases, methods for producing the enzymes, DNA encoding the enzymes, and methods for producing alcohols using the enzymes
US6682916B2 (en) *	2000-06-27	2004-01-27	Kaneka Corporation	Chlorohydroxyacetone derivative and process for producing optically active chloropropanediol derivative from the same
US6884607B2 (en) *	2000-12-07	2005-04-26	Sumitomo Chemical Company, Limited	Process for producing optically active 4-halo-3-hydroxybutanoate
RU2004102689A (ru) *	2001-07-02	2005-05-10	Канека Корпорейшн (Jp)	Способ модифицирования фермента и вариант оксидоредуктазы
JPWO2003040382A1 (ja) *	2001-11-09	2005-03-03	株式会社カネカ	光学活性クロマン誘導体の製造法および中間体
KR100522133B1 (ko) *	2002-01-26	2005-10-18	한국과학기술연구원	클루이베로마이세스 마르시아누스로부터 분리 및 정제된 카르보닐 환원효소 및 그 제조 방법
DE60323215D1 (de) *	2002-03-19	2008-10-09	Mitsubishi Chem Corp	Neue carbonylreduktase, diese codierendes gen und verfahren zur produktion optisch-aktiver alkohole damit
JP4228605B2 (ja) *	2002-07-02	2009-02-25	住友化学株式会社	改変型還元酵素、その遺伝子及びそれらの利用
JP4228606B2 (ja) *	2002-07-03	2009-02-25	住友化学株式会社	改変型還元酵素、その遺伝子及びそれらの利用
US20050272136A1 (en) *	2002-07-15	2005-12-08	Sumitomo Chemical Company, Limited	Process for producing 3-hydroxycyclohexanone
US7132267B2 (en) *	2002-08-09	2006-11-07	Codexis, Inc.	Enzymatic processes for the production of 4-substituted 3-hydroxybutyric acid derivatives and vicinal cyano, hydroxy substituted carboxylic acid esters
WO2004015132A2 (en) *	2002-08-09	2004-02-19	Codexis, Inc.	Enzymatic processes for the production of 4-substituted 3-hydroxybutyric acid derivatives
JP2007502124A (ja) *	2003-08-11	2007-02-08	コデクシス，インコーポレイテッド	改良ケトレダクターゼポリペプチドおよび関連ポリヌクレオチド
WO2006046455A1 (ja) *	2004-10-27	2006-05-04	Kaneka Corporation	新規カルボニル還元酵素、その遺伝子、およびその利用法
JPWO2006129628A1 (ja)	2005-05-31	2009-01-08	株式会社カネカ	光学活性２−置換プロパナール誘導体の製造法
JP2009114065A (ja) *	2006-02-21	2009-05-28	Kaneka Corp	（２ｒ，３ｒ）および（２ｓ，３ｓ）−３−フェニルイソセリン誘導体の製造法
WO2007138928A1 (ja)	2006-05-26	2007-12-06	Kaneka Corporation	光学活性３－アミノ－２－ヒドロキシプロピオン酸シクロプロピルアミド誘導体およびその塩の製造方法
WO2008042876A2 (en)	2006-10-02	2008-04-10	Codexis, Inc.	Compositions and methods for producing stereoisomerically pure statins and synthetic intermediates therefor
EP2123769B1 (en) *	2007-02-19	2016-05-18	Kaneka Corporation	Method for producing optically active 3-aminopiperidine or salt thereof
JP5603076B2 (ja)	2007-09-26	2014-10-08	株式会社カネカ	新規グルコース脱水素酵素
PL2445890T3 (pl) *	2009-06-22	2016-02-29	Sk Biopharmaceuticals Co Ltd	Sposób wytwarzania estru (R)-1-arylo-2-tetrazoliloetylowego kwasu karbaminowego
US8404461B2 (en)	2009-10-15	2013-03-26	SK Biopharmaceutical Co. Ltd.	Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
CN102686558A (zh)	2009-12-25	2012-09-19	株式会社钟化	光学活性3-取代戊二酸单酰胺的制造方法
CN111172124B (zh) *	2020-02-26	2022-07-22	复旦大学	一种羰基还原酶突变体及其在制备(r)-4-氯-3-羟基-丁酸酯中的应用
CN115433721B (zh) *	2022-06-24	2024-01-23	山东理工大学	一种羰基还原酶突变体及其应用

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JP3155107B2 (ja)	1993-01-12	2001-04-09	ダイセル化学工業株式会社	光学活性４−ハロ−３−ヒドロキシ酪酸エステルの製造方法
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1997
- 1997-09-01 JP JP53409498A patent/JP4012257B2/ja not_active Expired - Fee Related
- 1997-09-01 CA CA002280502A patent/CA2280502A1/en not_active Abandoned
- 1997-09-01 US US09/367,012 patent/US6218156B1/en not_active Expired - Lifetime
- 1997-09-01 ES ES97937861T patent/ES2235246T3/es not_active Expired - Lifetime
- 1997-09-01 CZ CZ0276199A patent/CZ298236B6/cs not_active IP Right Cessation
- 1997-09-01 WO PCT/JP1997/003051 patent/WO1998035025A1/ja not_active Ceased
- 1997-09-01 IL IL13124197A patent/IL131241A0/xx active IP Right Grant
- 1997-09-01 AT AT97937861T patent/ATE280218T1/de active
- 1997-09-01 AU AU40329/97A patent/AU4032997A/en not_active Abandoned
- 1997-09-01 DE DE69731317T patent/DE69731317T2/de not_active Expired - Lifetime
- 1997-09-01 KR KR10-1999-7007161A patent/KR100506134B1/ko not_active Expired - Fee Related
- 1997-09-01 EP EP97937861A patent/EP0967271B1/en not_active Expired - Lifetime
- 1997-09-01 SI SI9720093A patent/SI20120A/sl not_active IP Right Cessation
1998
- 1998-09-01 SK SK1056-99A patent/SK105699A3/sk unknown
1999
- 1999-08-04 IL IL131241A patent/IL131241A/en not_active IP Right Cessation
2001
- 2001-02-05 US US09/777,157 patent/US6448052B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ATE280218T1 (de)	2004-11-15
IL131241A (en)	2006-12-31
EP0967271B1 (en)	2004-10-20
KR20000070896A (ko)	2000-11-25
EP0967271A1 (en)	1999-12-29
EP0967271A4 (en)	2002-09-25
US6448052B2 (en)	2002-09-10
CZ298236B6 (cs)	2007-08-01
US20020006651A1 (en)	2002-01-17
SK105699A3 (en)	2000-06-12
CZ276199A3 (cs)	2000-03-15
CA2280502A1 (en)	1998-08-13
WO1998035025A1 (en)	1998-08-13
IL131241A0 (en)	2001-01-28
DE69731317T2 (de)	2006-02-23
US6218156B1 (en)	2001-04-17
AU4032997A (en)	1998-08-26
JP4012257B2 (ja)	2007-11-21
DE69731317D1 (de)	2004-11-25
ES2235246T3 (es)	2005-07-01
KR100506134B1 (ko)	2005-08-08

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Publication	Publication Date	Title
SI20120A (sl)	2000-06-30	Nova karbonil reduktaza, gen, ki omenjeno kodira in postopek za uporabo take reduktaze in gena
JPWO1998035025A1 (ja)	2000-07-11	新規カルボニル還元酵素、およびこれをコードする遺伝子、ならびにこれらの利用方法
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US7202069B2 (en)	2007-04-10	(R)-2-octanol dehydrogenases, methods for producing the enzymes, DNA encoding the enzymes, and methods for producing alcohols using the enzymes
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