JP2023522406A - 光学活性アミノアミド化合物のエナンチオ選択的化学酵素的合成 - Google Patents

光学活性アミノアミド化合物のエナンチオ選択的化学酵素的合成 Download PDF

Info

Publication number
JP2023522406A
JP2023522406A JP2022564282A JP2022564282A JP2023522406A JP 2023522406 A JP2023522406 A JP 2023522406A JP 2022564282 A JP2022564282 A JP 2022564282A JP 2022564282 A JP2022564282 A JP 2022564282A JP 2023522406 A JP2023522406 A JP 2023522406A
Authority
JP
Japan
Prior art keywords
seq
sequence
formula
nhase
βh146l
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
JP2022564282A
Other languages
English (en)
Japanese (ja)
Other versions
JP2023522406A5 (https=
Inventor
グリル，ビルジート
ヴィンクラー，マルジート
シュワーブ，ヘルムート
シュトローマイアー，ゲルノート
ドンスバッハ，カイ
アール． ヴァルトフォーゲル，ジークフリート
アルント，セバスティアン
ヴァイス，ドミニク
Original Assignee
ファルマツェル、ゲーエムベーハー
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.)
Filing date
Publication date
Application filed by ファルマツェル、ゲーエムベーハー filed Critical ファルマツェル、ゲーエムベーハー
Publication of JP2023522406A publication Critical patent/JP2023522406A/ja
Publication of JP2023522406A5 publication Critical patent/JP2023522406A5/ja
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/46—Ruthenium, rhodium, osmium or iridium
    • B01J23/462—Ruthenium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/12—Oxygen or sulfur atoms
    • 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
    • C12N9/88—Lyases (4.)
    • 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
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y402/00—Carbon-oxygen lyases (4.2)
    • C12Y402/01—Hydro-lyases (4.2.1)
    • C12Y402/01084—Nitrile hydratase (4.2.1.84)
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B1/00—Electrolytic production of inorganic compounds or non-metals
    • C25B1/01—Products
    • C25B1/24—Halogens or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B11/00—Electrodes; Manufacture thereof not otherwise provided for
    • C25B11/04—Electrodes; Manufacture thereof not otherwise provided for characterised by the material
    • C25B11/042—Electrodes formed of a single material
    • C25B11/043—Carbon, e.g. diamond or graphene
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/05—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/07—Oxygen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds
    • C25B3/01—Products
    • C25B3/09—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
    • C25B9/13—Single electrolytic cells with circulation of an electrolyte
    • C25B9/15—Flow-through cells
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B9/00—Cells or assemblies of cells; Constructional parts of cells; Assemblies of constructional parts, e.g. electrode-diaphragm assemblies; Process-related cell features
    • C25B9/17—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof
    • C25B9/19—Cells comprising dimensionally-stable non-movable electrodes; Assemblies of constructional parts thereof with diaphragms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electrochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Electrodes For Compound Or Non-Metal Manufacture (AREA)
  • Hydrogenated Pyridines (AREA)
JP2022564282A 2020-04-24 2021-04-23 光学活性アミノアミド化合物のエナンチオ選択的化学酵素的合成 Pending JP2023522406A (ja)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
EP20171351.8 2020-04-24
EP20171351 2020-04-24
EP20172908 2020-05-05
EP20172908.4 2020-05-05
EP20199842.4 2020-10-02
EP20199842 2020-10-02
EP20213425 2020-12-11
EP20213425.0 2020-12-11
PCT/EP2021/060648 WO2021214283A1 (en) 2020-04-24 2021-04-23 Enantioselective chemo-enzymatic synthesis of optically active amino amide compounds

Publications (2)

Publication Number Publication Date
JP2023522406A true JP2023522406A (ja) 2023-05-30
JP2023522406A5 JP2023522406A5 (https=) 2024-05-02

Family

ID=75562771

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2022564282A Pending JP2023522406A (ja) 2020-04-24 2021-04-23 光学活性アミノアミド化合物のエナンチオ選択的化学酵素的合成
JP2022564288A Pending JP2023523585A (ja) 2020-04-24 2021-04-23 複素環式α－アミノアミドの位置選択的酸化

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2022564288A Pending JP2023523585A (ja) 2020-04-24 2021-04-23 複素環式α－アミノアミドの位置選択的酸化

Country Status (6)

Country Link
US (2) US20230183177A1 (https=)
EP (2) EP4139468A1 (https=)
JP (2) JP2023522406A (https=)
KR (2) KR20230005242A (https=)
CN (2) CN115956127A (https=)
WO (2) WO2021214283A1 (https=)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114717582B (zh) * 2022-04-08 2023-09-19 云南大学 一种绿色电化学偶联制备茶碱类衍生物的方法
JP2026504109A (ja) * 2023-01-19 2026-02-03 ビ－エイイ－ システムズ パブリック リミテッド カンパニ－ フロー合成
CN116920880B (zh) * 2023-07-12 2025-07-18 江南大学 具有手性光学活性的硫化铜钴纳米花的制备方法及其应用
CN117000435B (zh) * 2023-08-17 2025-11-04 中南大学 一种辉钼矿抑制剂及高滑石型钼矿的选矿方法
CN120119268B (zh) * 2025-03-06 2025-12-09 南开大学 手性1-四氢萘酰胺类化合物的合成方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007115797A2 (en) * 2006-04-07 2007-10-18 B.R.A.I.N. Ag A group of novel enantioselective microbial nitrile hydratases with broad substrate specificity
WO2009009117A2 (en) * 2007-07-11 2009-01-15 Bioverdant, Inc. Chemoenzymatic processes for preparation of levetiracetam
WO2012169203A1 (ja) * 2011-06-07 2012-12-13 ダイヤニトリックス株式会社 改良型ニトリルヒドラターゼ
WO2019096677A1 (en) * 2017-11-14 2019-05-23 Columbia Srl Microbiological process for the preparation of amides

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2830941A (en) 1958-04-15 mehltretter
US2989371A (en) 1958-08-01 1961-06-20 Charles L Mehltretter Process for separation of sodium metaperiodate from sodium sulfate
DE19931847A1 (de) 1999-07-09 2001-01-11 Basf Ag Immobilisierte Lipase
NL1013348C2 (nl) * 1999-10-20 2001-04-23 Univ Eindhoven Tech Werkwijze voor het bereiden van perjodaat door oxidatie van jodaat in een elektrolysecel.
DE10019373A1 (de) 2000-04-18 2001-10-31 Pfreundt Gmbh & Co Kg Vorrichtung und Verfahren zur Steuerung eines Maschinenbauteils
DE10019380A1 (de) 2000-04-19 2001-10-25 Basf Ag Verfahren zur Herstellung von kovalent gebundenen biologisch aktiven Stoffen an Polyurethanschaumstoffen sowie Verwendung der geträgerten Polyurethanschaumstoffe für chirale Synthesen
DE10258652A1 (de) 2002-12-13 2004-06-24 Degussa Ag Verfahren zur elektrolytischen Herstellung von anorganischen Persauerstoffverbindungen
US20040225116A1 (en) * 2003-05-08 2004-11-11 Payne Mark S. Nucleic acid fragments encoding nitrile hydratase and amidase enzymes from comamonas testosteroni 5-MGAM-4D and recombinant organisms expressing those enzymes useful for the production of amides and acids
US20080146819A1 (en) * 2005-03-10 2008-06-19 Rubamin Limited Process for Preparing Levetiracetam
WO2008077035A2 (en) * 2006-12-18 2008-06-26 Dr. Reddy's Laboratories Ltd. Processes for the preparation of levetiracetam
US20110105488A1 (en) * 2008-03-21 2011-05-05 Chlorion Pharma, Inc. Substituted pyrrolidine and piperidine compounds, derivatives thereof, and methods for treating pain
CN102260721A (zh) * 2010-05-31 2011-11-30 尚科生物医药（上海）有限公司 一种用酶法制备（s）-2-氨基丁酰胺的方法
CN104450657B (zh) * 2014-11-06 2017-10-03 浙江大学 腈水合酶及其编码基因和应用
FR3053363B1 (fr) * 2016-06-30 2021-04-09 Herakles Systeme electrolytique pour la synthese du perchlorate de sodium avec anode a surface externe en diamant dope au bore
CN106544336A (zh) * 2016-12-06 2017-03-29 江南大学 一种对脂肪族二腈区域选择性提高的腈水合酶
CN108660131B (zh) * 2018-04-27 2020-07-21 浙江工业大学 固定化腈基水合酶和(s)-n-乙基吡咯烷-2-甲酰胺的制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007115797A2 (en) * 2006-04-07 2007-10-18 B.R.A.I.N. Ag A group of novel enantioselective microbial nitrile hydratases with broad substrate specificity
WO2009009117A2 (en) * 2007-07-11 2009-01-15 Bioverdant, Inc. Chemoenzymatic processes for preparation of levetiracetam
WO2012169203A1 (ja) * 2011-06-07 2012-12-13 ダイヤニトリックス株式会社 改良型ニトリルヒドラターゼ
WO2019096677A1 (en) * 2017-11-14 2019-05-23 Columbia Srl Microbiological process for the preparation of amides

Also Published As

Publication number Publication date
KR20230005243A (ko) 2023-01-09
CN115916746A (zh) 2023-04-04
US20230159452A1 (en) 2023-05-25
KR20230005242A (ko) 2023-01-09
CN115956127A (zh) 2023-04-11
WO2021214283A1 (en) 2021-10-28
EP4139468A1 (en) 2023-03-01
JP2023523585A (ja) 2023-06-06
EP4139283A2 (en) 2023-03-01
WO2021214278A2 (en) 2021-10-28
US20230183177A1 (en) 2023-06-15
WO2021214278A3 (en) 2021-12-02

Similar Documents

Publication Publication Date Title
JP2023522406A (ja) 光学活性アミノアミド化合物のエナンチオ選択的化学酵素的合成
US12252725B2 (en) Method for producing vanillin
US9512452B2 (en) L-lysine hydroxylase and production method for hydroxy-L-lysine and hydroxy-L-pipecolic acid using same
WO2010024444A1 (ja) 光学活性なアミン誘導体の製造方法
WO2010024445A1 (ja) 光学活性なアミン誘導体を製造するための方法
CA2479705C (en) Novel carbonyl reductase, gene encoding the same, and process for producing optically active alcohols using the same
JP5516664B2 (ja) Ｎ−アセチル−（Ｒ，Ｓ）−β−アミノ酸アシラーゼ遺伝子
US20220042051A1 (en) Lipoxygenase-catalyzed production of unsaturated c10-aldehydes from polyunsatrurated fatty acids
JP4648837B2 (ja) アミントランスアミナーゼ、および該アミントランスアミナーゼを利用した光学活性アミンの製造方法
JP2010187658A (ja) Ｄ−フェニルセリンデアミナーゼ及びその利用
JP4636590B2 (ja) Ｄ−β−ヒドロキシアミノ酸の製造方法
JP2011177029A (ja) 光学活性なアミン誘導体の製造方法
JP5119783B2 (ja) Ｎ−アセチル−（Ｒ，Ｓ）−β−アミノ酸アシラーゼ遺伝子
US20080265206A1 (en) Method for the Enzymatic Production of 5-Norbornen-2-Carboxylic Acid
JP4719535B2 (ja) ２，６−ジヒドロキシ安息香酸脱炭酸酵素、その酵素をコードするポリヌクレオチド、その製造方法、およびこれを利用した多価アルコ−ル芳香族化合物の製造方法
JP4414786B2 (ja) ２，６−ジヒドロキシ安息香酸脱炭酸酵素タンパク質をコードするｄｎａ及びこれを利用した多価アルコ−ル芳香族カルボン酸の製造方法
JP4938270B2 (ja) ニトリルヒドラターゼ、およびアミドの製造方法
JP2006115729A (ja) 光学活性β−ヒドロキシアミノ酸の晶析方法
KR101566158B1 (ko) L-아라보네이트를 생산하는 대장균 균주 ema2 및 이의 용도
WO2022138969A1 (ja) 変異型Ｌ－ピペコリン酸水酸化酵素及びそれを利用したｃｉｓ－５－ヒドロキシ－Ｌ－ピペコリン酸の製造方法
JP2006246815A (ja) Ｌ−フェニルセリン脱水素酵素の製造法
JP2011135888A (ja) ニトリルヒドラターゼ、およびアミドの製造方法

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20240422

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20240422

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20250507

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20251028