DK2367940T3 - Mutante penicillin-G-acylaser - Google Patents
Mutante penicillin-G-acylaser Download PDFInfo
- Publication number
- DK2367940T3 DK2367940T3 DK09796734.3T DK09796734T DK2367940T3 DK 2367940 T3 DK2367940 T3 DK 2367940T3 DK 09796734 T DK09796734 T DK 09796734T DK 2367940 T3 DK2367940 T3 DK 2367940T3
- Authority
- DK
- Denmark
- Prior art keywords
- acylase
- penicillin
- mutant
- ala
- synthetic
- Prior art date
Links
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Classifications
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- 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
- C12N9/14—Hydrolases (3)
- C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
- C12N9/84—Penicillin amidase (3.5.1.11)
-
- 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
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/09—Recombinant DNA-technology
- C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
- C12N15/70—Vectors or expression systems specially adapted for E. coli
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- 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
- C12P35/00—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin
- C12P35/04—Preparation of compounds having a 5-thia-1-azabicyclo [4.2.0] octane ring system, e.g. cephalosporin by acylation of the substituent in the 7 position
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- 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
- C12P37/00—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin
- C12P37/04—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin by acylation of the substituent in the 6 position
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y305/00—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5)
- C12Y305/01—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5) in linear amides (3.5.1)
- C12Y305/01011—Penicillin amidase (3.5.1.11), i.e. penicillin-amidohydrolase
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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Claims (12)
1. Mutant prokaryot penicillin-G-acylase, der har SEQ ID NO: 1 eller har en sekvens, der har 80 %-100 % identitet med SEQ ID NO: 1, der er afledt fra en vildtype-penicillin-G-acylase, der er kendetegnet ved, at mutanten har alanin i position B24 og har leucin i position B460 ifølge aminosyrenummereringen i Escherichia coli-penicillin-G-acylase, der har aminosyresekvensen, der er vist i SEQ ID NO: 1.
2. Mutant prokaryot penicillin-G-acylase ifølge krav 1, der har leucin i position A3 eller har lysin i position A90 eller har glutaminsyre i position A192 og/eller har leucin i position B148.
3. Nukleinsyresekvens, der koder for den mutante penicillin-G-acylase ifølge et hvilket som helst af ovennævnte krav.
4. Ekspressionsvektor, der omfatter nukleinsyresekvensen ifølge krav 3.
5. Værtscelle, der omfatter ekspressionsvektoren ifølge krav 4 .
6. Fremgangsmåde til fremstilling af den mutante penicillin-G-acylase ifølge et hvilket som helst af kravene 1-2.
7. Fremgangsmåde til fremstilling af et semisyntetisk β-lactam-antibiotikum, som omfatter en enzymatisk kobling af en aktiveret sidekæde til en β-lactam-kerne, der er kendetegnet ved anvendelse af den mutante prokaryote penicillin-G-acylase ifølge et hvilket som helst af kravene 1-2.
8. Fremgangsmåde ifølge krav 7, hvor det semisyntetiske β-lactam-antibiotikum er valgt fra gruppen, der består af semisyntetiske penicilliner og semisyntetiske cephalosporiner.
9. Fremgangsmåde ifølge krav 8, hvor den semisyntetiske penicillin er amoxicillin eller ampicillin.
10. Fremgangsmåde ifølge krav 8, hvor den semisyntetiske cephalosporin er cefalexin, cefadroxil eller cefradin.
11. Fremgangsmåde til fremstilling af amoxicillin i nærvær af en acylase ifølge et hvilket som helst af kravene 1-2, der katalyserer koblingen af HPG i aktiveret form til 6-APA, hvor molforholdet mellem den aktiverede HPG og 6-APA er < 3,0, og udbyttet af amoxicillin baseret på 6-APA (mol/mol) og målt efter den enzymatisk koblingsreaktion er > 90 %.
12. Fremgangsmåde ifølge krav 11, hvor acylasen er i stand til at danne amoxicillin ud fra 500 mmol pr. liter HPGM og 530 mmol pr. liter 6-APA, som resulterer i mindre end 5 mmol pr. liter 6-APA ved afslutningen af omdannelsen, der udføres under betingelserne som beskrevet i test A.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08172831 | 2008-12-23 | ||
| PCT/EP2009/067752 WO2010072765A2 (en) | 2008-12-23 | 2009-12-22 | Mutant penicillin g acylases |
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| DK2367940T3 true DK2367940T3 (da) | 2018-03-05 |
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| DK09796734.3T DK2367940T3 (da) | 2008-12-23 | 2009-12-22 | Mutante penicillin-G-acylaser |
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| EP (1) | EP2367940B1 (da) |
| JP (1) | JP2012513196A (da) |
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| SMT201800111T1 (it) | 2010-09-07 | 2018-05-02 | Dsm Sinochem Pharm Nl Bv | Processo per la produzione di cefalosporine |
| WO2012175587A2 (en) | 2011-06-23 | 2012-12-27 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Novel crystalline cefoperazone intermediate |
| CN103635585A (zh) * | 2011-06-23 | 2014-03-12 | 中化帝斯曼制药有限公司荷兰公司 | 用青霉素g酰化酶制备3’-硫代头孢菌素的方法 |
| US20150112057A1 (en) * | 2011-06-23 | 2015-04-23 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Novel crystalline cefoperazone intermediate |
| WO2013057196A1 (en) | 2011-10-20 | 2013-04-25 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Process for the preparation of cefamandole nafate |
| WO2013057197A1 (en) | 2011-10-20 | 2013-04-25 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Process for the formylation of cefamandole |
| RU2564578C2 (ru) * | 2012-04-25 | 2015-10-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | МУТАНТ ПЕНИЦИЛЛИНАЦИЛАЗЫ ИЗ E.coli С УЛУЧШЕННЫМИ СВОЙСТВАМИ |
| CN103074320B (zh) * | 2012-05-25 | 2018-06-08 | 石药集团中奇制药技术（石家庄）有限公司 | 含有一个或几个点突变的青霉素g酰化酶 |
| CN103667418B (zh) * | 2013-12-18 | 2015-03-25 | 华北制药河北华民药业有限责任公司 | 高活性β-内酰胺抗生素合成用酶的高通量筛选方法 |
| DK3292136T3 (da) * | 2015-05-07 | 2021-03-22 | Codexis Inc | Penicillin-g-acylaser |
| CN105087533B (zh) * | 2015-09-30 | 2018-03-27 | 湖南福来格生物技术有限公司 | 一种青霉素g酰化酶的突变体及其制备方法和应用 |
| CN105483105B (zh) * | 2016-02-23 | 2018-08-31 | 上海星维生物技术有限公司 | 一种青霉素g酰化酶突变体 |
| WO2017186864A1 (en) | 2016-04-27 | 2017-11-02 | Sandoz Ag | Enzymatic process for the production of beta-lactam antibiotics in the presence of particulate inoculum |
| US10745681B2 (en) | 2017-01-05 | 2020-08-18 | Codexis, Inc. | Penicillin-G acylases |
| CN108660127B (zh) * | 2017-03-27 | 2021-09-21 | 珠海联邦制药股份有限公司 | 一种人工设计的青霉素g酰化酶原及其编码序列与应用 |
| CN107099523B (zh) * | 2017-06-15 | 2019-09-27 | 清华大学 | 头孢拉定合成酶突变体及其编码基因 |
| KR101985911B1 (ko) * | 2017-12-28 | 2019-06-04 | 아미코젠주식회사 | Achromobacter sp. CCM 4824 유래 페니실린 G 아실라제 변이체 및 이의 이용 |
| KR102363768B1 (ko) * | 2019-11-15 | 2022-02-16 | 아미코젠주식회사 | 세파졸린 생산성이 증가된 페니실린 g 아실라제 변이체 및 이의 이용 |
| KR20220125219A (ko) * | 2020-01-08 | 2022-09-14 | 페르멘타 바이오테크 리미티드 | 아크로모박터 ccm4824의 돌연변이 페니실린 g 아실라아제 |
| CN111500564B (zh) * | 2020-06-02 | 2022-01-18 | 南京工业大学 | 青霉素g酰化酶突变体及其在酶法合成头孢孟多中的应用 |
| WO2022195603A1 (en) * | 2021-03-18 | 2022-09-22 | Fermenta Biotech Limited | A ONE STEP PROCESS FOR THE ENZYMATIC SYNTHESIS OF SEMISYNTHETIC β-LACTAM ANTIBIOTICS |
| CN113567607A (zh) * | 2021-07-23 | 2021-10-29 | 河北冀安检测服务有限公司 | 一种头孢克洛中青霉素g酰基转移酶含量的检测方法 |
| CN113584008B (zh) * | 2021-07-30 | 2023-04-11 | 湖南福来格生物技术有限公司 | 一种青霉素g酰化酶突变体及其应用 |
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| PT83746B (pt) | 1985-11-15 | 1988-08-17 | Gist Brocades Nv | Processo para a preparacao de novos biocatalisadores imobilizados e para a producao de etanol por fermentacao |
| US5891703A (en) * | 1994-08-12 | 1999-04-06 | Gist-Hrocades | Mutated penicillin G acylase genes |
| AU6659296A (en) * | 1995-07-18 | 1997-02-18 | Gist-Brocades B.V. | An improved immobilized penicillin g acylase |
| HU226348B1 (en) | 1996-11-05 | 2008-09-29 | Bristol Myers Squibb Co | Mutant penicillin g acylases |
| US6562958B1 (en) * | 1998-06-09 | 2003-05-13 | Genome Therapeutics Corporation | Nucleic acid and amino acid sequences relating to Acinetobacter baumannii for diagnostics and therapeutics |
| US20050124029A1 (en) | 2001-12-27 | 2005-06-09 | Alkema Wynand B.L. | Process for the preparation of a betha- lactam antibiotic with mutated penicillin acylase |
| DE10251747A1 (de) | 2002-11-05 | 2004-05-19 | Tuhh-Technologie-Gmbh | Gentechnisch veränderte Penicillinamidase und Verfahren zu ihrer Herstellung |
| CN100507000C (zh) * | 2003-07-03 | 2009-07-01 | 帝斯曼知识产权资产管理有限公司 | 制备头孢拉定的方法 |
| LT1641933T (lt) * | 2003-07-03 | 2018-04-10 | Dsm Sinochem Pharmaceuticals Netherlands B.V. | Cefradino gamybos būdas |
| EP1831390B1 (en) * | 2004-12-27 | 2014-11-19 | DSM Sinochem Pharmaceuticals Netherlands B.V. | Process for the synthesis of cefaclor |
| CN101177688B (zh) | 2006-11-08 | 2010-12-01 | 中国科学院上海生命科学研究院 | 突变青霉素g酰化酶、其重组表达质粒及转化的工程菌株 |
| JP2010520752A (ja) | 2007-03-09 | 2010-06-17 | ディーエスエム アイピー アセッツ ビー．ブイ． | ベータ−ラクタム化合物の調製方法 |
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Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0922510B8 (pt) | 2021-05-25 |
| NO2367940T3 (da) | 2018-04-21 |
| SI2367940T1 (en) | 2018-04-30 |
| CN102264904A (zh) | 2011-11-30 |
| WO2010072765A2 (en) | 2010-07-01 |
| HRP20180318T1 (hr) | 2018-03-23 |
| EP2367940A2 (en) | 2011-09-28 |
| CN103642780B (zh) | 2017-06-20 |
| SMT201800100T1 (it) | 2018-03-08 |
| KR101735126B1 (ko) | 2017-05-12 |
| LT2367940T (lt) | 2018-03-26 |
| KR20110099137A (ko) | 2011-09-06 |
| JP2012513196A (ja) | 2012-06-14 |
| WO2010072765A3 (en) | 2010-08-26 |
| SG171964A1 (en) | 2011-07-28 |
| CN103642780A (zh) | 2014-03-19 |
| US20110256585A1 (en) | 2011-10-20 |
| CN102264904B (zh) | 2013-10-23 |
| US8541199B2 (en) | 2013-09-24 |
| BRPI0922510A2 (pt) | 2015-08-04 |
| MX2011006802A (es) | 2011-07-20 |
| EP2367940B1 (en) | 2017-11-22 |
| HUE036302T2 (hu) | 2018-07-30 |
| BRPI0922510B1 (pt) | 2021-01-19 |
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