CN102131813B - 用于制备基本上立体异构纯的稠合二环脯氨酸化合物的生物催化方法 - Google Patents

用于制备基本上立体异构纯的稠合二环脯氨酸化合物的生物催化方法 Download PDF

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CN102131813B
CN102131813B CN200980133157.9A CN200980133157A CN102131813B CN 102131813 B CN102131813 B CN 102131813B CN 200980133157 A CN200980133157 A CN 200980133157A CN 102131813 B CN102131813 B CN 102131813B
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compound
seq
monoamine oxidase
structural formula
amino acid
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CN102131813A (zh
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本杰明·米杰茨
希拉·慕莱
杰克·梁
利萨·M·纽曼
张希云
詹姆士·拉隆德
迈克尔·D·克莱
军·朱
约翰·M·格鲁伯
杰弗里·科尔贝克
小约翰·D·芒格
亚加迪什·马维纳哈利
罗杰·谢尔登
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Codexis Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • 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
    • C12P13/24—Proline; Hydroxyproline; Histidine
    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y104/00—Oxidoreductases acting on the CH-NH2 group of donors (1.4)
    • C12Y104/03—Oxidoreductases acting on the CH-NH2 group of donors (1.4) with oxygen as acceptor (1.4.3)
    • C12Y104/03004—Monoamine oxidase (1.4.3.4)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CN200980133157.9A 2008-06-24 2009-06-23 用于制备基本上立体异构纯的稠合二环脯氨酸化合物的生物催化方法 Active CN102131813B (zh)

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US7524308P 2008-06-24 2008-06-24
US61/075,243 2008-06-24
PCT/US2009/048255 WO2010008828A2 (en) 2008-06-24 2009-06-23 Biocatalytic processes for the preparation of substantially stereomerically pure fused bicyclic proline compounds

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CN2012101130855A Pending CN102816106A (zh) 2008-06-24 2009-06-23 用于制备基本上立体异构纯的稠合二环脯氨酸化合物的生物催化方法

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US (4) US8178333B2 (https=)
EP (2) EP2307419B1 (https=)
JP (1) JP2011525533A (https=)
KR (1) KR20110048509A (https=)
CN (2) CN102131813B (https=)
AU (1) AU2009271325A1 (https=)
CA (1) CA2728226A1 (https=)
ES (1) ES2438576T3 (https=)
MX (1) MX2010014500A (https=)
WO (1) WO2010008828A2 (https=)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7811283B2 (en) * 2003-11-19 2010-10-12 Covidien Ag Open vessel sealing instrument with hourglass cutting mechanism and over-ratchet safety
MX2010014500A (es) * 2008-06-24 2011-05-30 Codexis Inc Procedimientos biocataliticos para la preparacion de compuestos de prolina biciclica fusionada sustancialmente estereomericamente puros.
US8828930B2 (en) 2009-07-30 2014-09-09 Merck Sharp & Dohme Corp. Hepatitis C virus NS3 protease inhibitors
US8686145B2 (en) 2010-02-25 2014-04-01 Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patientenzorg C/O Technology Transfer Officer VU & Vumc Process for the preparation of α-acyloxy β-formamido amides
JP2013010732A (ja) 2011-06-03 2013-01-17 Sumitomo Chemical Co Ltd プロリン化合物の製造方法
CN103450066B (zh) * 2012-05-30 2017-03-15 博瑞生物医药（苏州）股份有限公司 特拉匹韦中间体的制备方法
AR091192A1 (es) 2012-05-30 2015-01-21 Chemo Iberica Sa Procedimiento multicomponente para la preparacion de compuestos biciclicos
ITMI20122205A1 (it) * 2012-12-20 2014-06-21 Dipharma Francis Srl Sintesi di un intermedio di un inibitore delle proteasi virali
WO2014096374A1 (en) 2012-12-21 2014-06-26 Sandoz Ag Process for the synthesis of pyrrolidines and pyrroles
ITMI20130706A1 (it) * 2013-04-30 2014-10-31 Dipharma Francis Srl Procedimento per la preparazione di un inibitore delle proteasi virali e suoi intermedi
CN104292146B (zh) * 2013-06-24 2017-04-26 上海医药工业研究院 特拉匹韦中间体及其制备方法
RU2016116253A (ru) 2013-09-27 2017-11-01 Кодексис, Инк. Автоматизированный скрининг вариантов фермента
CN105441401B (zh) * 2014-09-01 2019-11-08 上海弈柯莱生物医药科技有限公司 一种单胺氧化酶及其在合成手性氮杂双环化合物中的应用
CN105624128B (zh) * 2014-11-26 2020-03-17 上海弈柯莱生物医药科技有限公司 一种固定化单胺氧化酶及其在合成手性氮杂双环化合物中的应用
JP7674810B2 (ja) * 2017-02-03 2025-05-12 アンティドートゥ・セラピューティクス・インコーポレイテッド 新規ニコチン分解酵素変異体
CN115927216B (zh) * 2021-08-10 2025-03-25 深圳瑞德林生物技术有限公司 一种s-尼古丁的制备方法
CN114292825B (zh) * 2021-12-17 2023-08-18 武汉大学 一种托品酮的合成方法
CN114317631B (zh) * 2021-12-17 2023-11-07 武汉大学 单胺氧化酶在制备托品酮中的应用
CN116731991A (zh) * 2022-03-10 2023-09-12 青岛清原化合物有限公司 单胺氧化酶及其应用
WO2023173058A2 (en) * 2022-03-11 2023-09-14 Codexis, Inc. Engineered monoamine oxidases for the preparation of stereomerically pure fused bicyclic proline compounds
JP2025510621A (ja) * 2022-03-31 2025-04-15 青島清原化合物有限公司 モノアミン酸化酵素及びその応用
CN114774382A (zh) * 2022-04-07 2022-07-22 扬州联澳生物医药有限公司 立体选择性制备6,6-二甲基-3-氮杂双环[3.1.0]己烯化合物的方法
CN114751853B (zh) * 2022-04-11 2023-10-13 扬州联澳生物医药有限公司 6,6-二甲基-3-氮杂双环[3.1.0]己烷化合物的制备方法
CN114958938B (zh) * 2022-05-13 2023-12-08 金达威生物技术(江苏)有限公司 一种稠合二环脯氨酸甲酯盐酸盐的制备方法
CN114736882B (zh) * 2022-05-20 2023-09-22 苏州百福安酶技术有限公司 一种单胺氧化酶及其应用
CN116064444B (zh) * 2022-08-24 2025-05-06 长兴制药股份有限公司 一种单胺氧化酶及波普瑞韦双环脯氨酸片段的制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003080855A2 (en) * 2002-03-19 2003-10-02 Glaxo Group Limited Deracemisation of amines
WO2006061585A1 (en) * 2004-12-06 2006-06-15 Isis Innovation Limited Pyrrolidine compounds
CN1946692A (zh) * 2004-02-27 2007-04-11 先灵公司 作为丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的3,4－(环戊基)－稠合的脯氨酸化合物

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4183857A (en) * 1978-07-06 1980-01-15 Shell Oil Company 3-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dione
CA1117125A (en) * 1978-03-01 1982-01-26 Ronald F. Mason 2-cyano-3-azabicyclo¬3.1.0|hexane compounds
US4225499A (en) * 1978-07-06 1980-09-30 Shell Oil Company Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile
CA1116615A (en) * 1978-09-27 1982-01-19 Ronald F. Mason Sulfonic acid salt of 2-cyano-3-azabicyclo[3.1.0]hexane
DE2962910D1 (en) * 1978-10-27 1982-07-08 Shell Int Research A process for the preparation of 3-azabicyclo(3.1.0)hexane derivatives and modifications thereof
CA1117128A (en) * 1978-10-27 1982-01-26 Derek A. Wood 2-cyano-3-azabicyclo(3.1.0)hexane
LU88621I2 (fr) * 1980-10-23 1995-09-01 Schering Corp Sandopril
DE3211676A1 (de) 1982-03-30 1983-10-06 Hoechst Ag Neue derivate von cycloalka (c) pyrrol-carbonsaeuren, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie neue cycloalka (c) pyrrol-carbonsaeuren als zwischenstufen und verfahren zu deren herstellung
DE3322530A1 (de) * 1983-06-23 1985-01-10 Hoechst Ag, 6230 Frankfurt Verfahren zur herstellung von mono-, bi- und tricyclischen aminosaeuren
DE69133402T2 (de) 1990-04-04 2004-11-11 Chiron Corp. (N.D.Ges.D. Staates Delaware), Emeryville Protease von hepatitis-c-virus
US6117679A (en) 1994-02-17 2000-09-12 Maxygen, Inc. Methods for generating polynucleotides having desired characteristics by iterative selection and recombination
US5605793A (en) 1994-02-17 1997-02-25 Affymax Technologies N.V. Methods for in vitro recombination
US5837458A (en) 1994-02-17 1998-11-17 Maxygen, Inc. Methods and compositions for cellular and metabolic engineering
US6335160B1 (en) 1995-02-17 2002-01-01 Maxygen, Inc. Methods and compositions for polypeptide engineering
FI964808A0 (fi) 1994-06-03 1996-12-02 Novo Nordisk Biotech Inc Puhdistetut Myceliophthora lakkaasit ja niitä koodaavat nukleiinihapot
CN101659926A (zh) 1994-06-30 2010-03-03 诺沃奇梅兹有限公司 非毒性、非产毒性、非致病性镰孢属表达系统及所用启动子和终止子
FI104465B (fi) 1995-06-14 2000-02-15 Valio Oy Proteiinihydrolysaatteja allergioiden hoitamiseksi tai estämiseksi, niiden valmistus ja käyttö
US6537746B2 (en) 1997-12-08 2003-03-25 Maxygen, Inc. Method for creating polynucleotide and polypeptide sequences
JPH11253162A (ja) 1998-03-10 1999-09-21 Mitsubishi Chemical Corp モノアミンオキシダーゼをコードするｄｎａ
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
US6858018B1 (en) 1998-09-28 2005-02-22 Vyteris, Inc. Iontophoretic devices
SE521927C2 (sv) 1998-10-01 2003-12-16 Delsing Jerker Metod och anordning för interferometrimätning
US7504490B1 (en) * 1998-10-16 2009-03-17 Oscient Pharmaceuticals Corporation Nucleic acid and amino acid sequences relating to Apergillus fumigatus for diagnostics and therapeutics
JP4221100B2 (ja) 1999-01-13 2009-02-12 エルピーダメモリ株式会社 半導体装置
EP1272967A2 (en) 2000-03-30 2003-01-08 Maxygen, Inc. In silico cross-over site selection
DK1385870T3 (da) 2000-07-21 2010-07-05 Schering Corp Peptider som inhibitorer af NS3-serinprotease fra hepatitis C-virus
US7244721B2 (en) 2000-07-21 2007-07-17 Schering Corporation Peptides as NS3-serine protease inhibitors of hepatitis C virus
SV2003000617A (es) * 2000-08-31 2003-01-13 Lilly Co Eli Inhibidores de la proteasa peptidomimetica ref. x-14912m
US7214786B2 (en) * 2000-12-14 2007-05-08 Kovalic David K Nucleic acid molecules and other molecules associated with plants and uses thereof for plant improvement
JP4363183B2 (ja) * 2001-06-08 2009-11-11 三菱化学株式会社 アザ糖化合物
US7241796B2 (en) 2001-10-24 2007-07-10 Vertex Pharmaceuticals Inc. Inhibitors of serine proteases, particularly HCV NS3-NS4A protease
US20040029129A1 (en) * 2001-10-25 2004-02-12 Liangsu Wang Identification of essential genes in microorganisms
US7314974B2 (en) * 2002-02-21 2008-01-01 Monsanto Technology, Llc Expression of microbial proteins in plants for production of plants with improved properties
GB0211418D0 (en) 2002-05-17 2002-06-26 Glaxo Group Ltd Compounds
ES2354817T3 (es) 2003-06-17 2011-03-18 Schering Corporation Procedimiento y productos intermedios para la preparación de 3-azabiciclo[3.1.0]hexano-2-carboxilatos de (1r,2s,5s)-6,6-dimetilo o sus sales.
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
PT1745040E (pt) 2004-02-23 2010-03-08 Glaxo Group Ltd Derivados do azabiciclo3.1.0-hexano úteis como moduladores dos receptores d3 da dopamina
US8399615B2 (en) 2005-08-19 2013-03-19 Vertex Pharmaceuticals Incorporated Processes and intermediates
PL385229A1 (pl) 2005-08-19 2008-09-29 Vertex Pharmaceuticals Incorporated Sposoby i związki pośrednie
WO2007023382A2 (en) * 2005-08-25 2007-03-01 Pfizer Inc. Pyrimidine amino pyrazole compounds, potent kinase inhibitors
WO2007029086A2 (en) * 2005-09-05 2007-03-15 Ranbaxy Laboratories Limited Derivatives of 3-azabicyclo[3.1.0]hexane as dipeptidyl peptidase-iv inhibitors
WO2007075790A1 (en) 2005-12-22 2007-07-05 Schering Corporation Process for the preparation of 6, 6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds and enantiomeric salts thereof
EP2129658A2 (en) * 2006-12-20 2009-12-09 Schering Corporation Process for the preparation of 6,6-dimethyl-3-azabicyclo- [3.1.0]- hexane compounds utilizing bisulfite intermediate
EP2225203A1 (en) * 2007-11-28 2010-09-08 Schering Corporation Dehydrohalogenation process for the preparation of intermediates useful in providing 6,6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds
MX2010014500A (es) * 2008-06-24 2011-05-30 Codexis Inc Procedimientos biocataliticos para la preparacion de compuestos de prolina biciclica fusionada sustancialmente estereomericamente puros.
EP2416765B1 (en) 2009-04-06 2016-03-30 PTC Therapeutics, Inc. Hcv inhibitor and therapeutic agent combinations
WO2010117936A1 (en) 2009-04-06 2010-10-14 Schering Corporation Combinations of a hcv inhibitor such as bicyclic pyrrole derivatives and a therapeutic agent

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003080855A2 (en) * 2002-03-19 2003-10-02 Glaxo Group Limited Deracemisation of amines
CN1946692A (zh) * 2004-02-27 2007-04-11 先灵公司 作为丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的3,4－(环戊基)－稠合的脯氨酸化合物
WO2006061585A1 (en) * 2004-12-06 2006-06-15 Isis Innovation Limited Pyrrolidine compounds

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
A Chemo-Enzymatic Route to Enantiomerically Pure Cyclic Tertiary Amines;Colin J.Dunsmore,等;《J.AM.CHEM.SOC》;20060201;第128卷(第7期);第2224-2225页，尤其是2224页表1,2 *
Amine–boranes: effective reducing agents for the deracemisation of DL-amino acids using L-amino acid oxidase from Proteus myxofaciens;Francois-Rene Alexandre,等;《Tetrahedron》;20020121;第43卷(第4期);第707-709页，尤其是707页图1 *
Directed Evolution of an Amine Oxidase Possessing both Broad Substrate Specificity and High Enantioselectivity;Reuben Carr,等;《Angew.Chem》;20031013;第115卷(第39期);第4955-4958页，尤其是4955-4956页表1,3 *
单胺氧化酶;陈剑锋，等;《生物化学与生物物理进展》;20001025;第27卷(第5期);第503-507页，尤其是504页左栏第段 *

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