JP6343604B2 - BCN基を含むアミノ酸をコードする直交性コドンと、直交性PylRS合成酵素とを使用して、BCN基を含むアミノ酸をポリペプチドに取り込む方法 - Google Patents

BCN基を含むアミノ酸をコードする直交性コドンと、直交性PylRS合成酵素とを使用して、BCN基を含むアミノ酸をポリペプチドに取り込む方法 Download PDF

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JP6343604B2
JP6343604B2 JP2015512124A JP2015512124A JP6343604B2 JP 6343604 B2 JP6343604 B2 JP 6343604B2 JP 2015512124 A JP2015512124 A JP 2015512124A JP 2015512124 A JP2015512124 A JP 2015512124A JP 6343604 B2 JP6343604 B2 JP 6343604B2
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bcn
amino acid
tetrazine
polypeptide
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JP2015523965A (ja
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ジェイソン チン
ジェイソン チン
キャスリン ラング
キャスリン ラング
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K1/00General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/006General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06Esters of carbamic acids
    • C07C271/08Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K1/00General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/13Labelling of peptides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07KPEPTIDES
    • C07K2/00Peptides of undefined number of amino acids; Derivatives thereof
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    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12NMICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/93Ligases (6)
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12YENZYMES
    • C12Y601/00Ligases forming carbon-oxygen bonds (6.1)
    • C12Y601/01Ligases forming aminoacyl-tRNA and related compounds (6.1.1)
    • C12Y601/01026Pyrrolysine-tRNAPyl ligase (6.1.1.26)
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14All rings being cycloaliphatic
    • C07C2602/24All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

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  • Medicinal Chemistry (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
  • Wood Science & Technology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
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  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
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  • Urology & Nephrology (AREA)
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  • Immunology (AREA)
  • Physics & Mathematics (AREA)
  • Food Science & Technology (AREA)
  • Cell Biology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Peptides Or Proteins (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
JP2015512124A 2012-05-18 2013-05-15 BCN基を含むアミノ酸をコードする直交性コドンと、直交性PylRS合成酵素とを使用して、BCN基を含むアミノ酸をポリペプチドに取り込む方法 Active JP6343604B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB1208875.3 2012-05-18
GBGB1208875.3A GB201208875D0 (en) 2012-05-18 2012-05-18 Methods
GB1210303.2 2012-06-08
GBGB1210303.2A GB201210303D0 (en) 2012-06-08 2012-06-08 Polypeptides and methods
PCT/GB2013/051249 WO2013171485A1 (en) 2012-05-18 2013-05-15 Methods of incorporating an amino acid comprising a bcn group into a polypeptide using an orthogonal codon encoding it and an orthorgonal pylrs synthase.

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JP2015523965A JP2015523965A (ja) 2015-08-20
JP6343604B2 true JP6343604B2 (ja) 2018-06-13

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US (3) US20150148525A1 (enExample)
EP (1) EP2852664B1 (enExample)
JP (1) JP6343604B2 (enExample)
CN (2) CN104718285A (enExample)
BR (1) BR112014028588B1 (enExample)
CA (1) CA2873793C (enExample)
IN (1) IN2014DN09922A (enExample)
WO (1) WO2013171485A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6343604B2 (ja) * 2012-05-18 2018-06-13 メディカル リサーチ カウンシル BCN基を含むアミノ酸をコードする直交性コドンと、直交性PylRS合成酵素とを使用して、BCN基を含むアミノ酸をポリペプチドに取り込む方法
CN106010507A (zh) * 2013-12-31 2016-10-12 深圳先进技术研究院 由染料分子标记的四嗪探针及其制备方法和应用
GB2528227A (en) 2014-03-14 2016-01-20 Medical Res Council Cyclopropene amino acids and methods
WO2016176689A1 (en) 2015-04-30 2016-11-03 Oregon State University Reagents and methods for bioorthogonal labeling of biomolecules in living cells
EP3360960A4 (en) * 2015-08-19 2019-03-20 Riken ANTIBODIES WITH INGREDIENTS OF NON-NATURAL AMINO ACID
CN105254655B (zh) * 2015-11-20 2017-03-22 江汉大学 一种基于bodipy的荧光氨基酸及其合成方法与应用
CN106565762B (zh) * 2016-11-17 2018-10-23 陕西师范大学 一种原位产生近红外荧光的bodipy类染料及其制备和应用
JP7216006B2 (ja) 2017-03-22 2023-01-31 ジェネンテック, インコーポレイテッド ヒドロゲル架橋ヒアルロン酸プロドラッグ組成物及び方法
JOP20190245A1 (ar) 2017-04-20 2019-10-15 Novartis Ag أنظمة توصيل إطلاق مستدام تتضمن روابط بلا أثر لنقطة الربط
US11560384B2 (en) 2017-05-04 2023-01-24 University Of Utah Research Foundation Benzonorbornadiene derivatives and reactions thereof
AR111963A1 (es) * 2017-05-26 2019-09-04 Univ California Método y moléculas
AR116566A1 (es) 2018-10-03 2021-05-19 Novartis Ag Administración sostenida de polipéptidos similares a la angiopoyetina 3
GB201817444D0 (en) 2018-10-26 2018-12-12 Res & Innovation Uk Methods and compositions
CN111849929B (zh) * 2019-04-30 2021-05-11 苏州鲲鹏生物技术有限公司 高效引入赖氨酸衍生物的氨酰基—tRNA合成酶
GB201906775D0 (en) 2019-05-14 2019-06-26 Res & Innovation Uk Synthetic genome
IL267744A (en) * 2019-06-30 2019-08-29 Nat Inst Biotechnology Negev Ltd Labelling molecules and methods of use thereof
CN115701451B (zh) * 2021-08-02 2023-08-01 宁波鲲鹏生物科技有限公司 高效引入赖氨酸衍生物的氨酰基-tRNA合成酶及其应用
AU2024263582A1 (en) 2023-04-28 2025-10-09 United Kingdom Research And Innovation tRNA-BASED METHODS AND RELATED COMPOSITIONS
GB202307998D0 (en) 2023-05-29 2023-07-12 Res & Innovation Uk Aminoacyl-irna synthetase sets
CN119613545B (zh) * 2024-12-16 2025-09-16 天津大学 非天然氨基酸修饰的抗ccl5纳米抗体

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040029129A1 (en) * 2001-10-25 2004-02-12 Liangsu Wang Identification of essential genes in microorganisms
CA2527877A1 (en) 2003-06-18 2005-01-13 The Scripps Research Institute Unnatural reactive amino acid genetic code additions
ATE386133T1 (de) * 2003-07-07 2008-03-15 Scripps Research Inst Zusammensetzungen der orthogonalen lysyl-trna und aminoacyl-trna synthetase paaren und ihre verwendungen
US7741071B2 (en) 2003-12-18 2010-06-22 The Scripps Research Institute Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells
BRPI0515547A (pt) 2004-09-21 2008-07-29 Scripps Research Inst incorporação in vivo de aminoácidos alquinil em proteìnas em eubacterias
WO2006110182A2 (en) 2004-10-27 2006-10-19 The Scripps Research Institute Orthogonal translation components for the in vivo incorporation of unnatural amino acids
US8431558B2 (en) * 2004-11-01 2013-04-30 The Regents Of The University Of California Compositions and methods for modification of biomolecules
JP2007037445A (ja) 2005-08-02 2007-02-15 Institute Of Physical & Chemical Research tRNA合成方法、核酸、アミノアシルtRNA合成方法及び非天然型アミノ酸組み込み蛋白質の製造方法
US20090081669A1 (en) 2006-02-01 2009-03-26 Encode Bio, Inc. Fluorescent Assays Using Orthogonal tRNA - Aminoacyl Synthetase Pairs
US20080096819A1 (en) 2006-05-02 2008-04-24 Allozyne, Inc. Amino acid substituted molecules
US20090110662A1 (en) 2007-04-30 2009-04-30 Intezyne Technologies, Inc. Modification of biological targeting groups for the treatment of cancer
JP5590649B2 (ja) * 2007-09-20 2014-09-17 独立行政法人理化学研究所 変異体ピロリジル−tRNA合成酵素及びこれを用いる非天然アミノ酸組み込みタンパク質の製造方法
GB0721291D0 (en) * 2007-10-30 2007-12-12 Medical Res Council Methods and compositions
US20120045761A1 (en) * 2009-02-25 2012-02-23 Bigtec Private Limited Probes and primers for detection of chikungunya
GB2470770A (en) 2009-06-04 2010-12-08 Medical Res Council Incorporation of unnatural amino acids having an orthogonal functional group into polypeptides using orthogonal tRNA/tRNA synthetase pairs
GB0917240D0 (en) * 2009-10-01 2009-11-18 Medical Res Council Incorporation of methyl lysine into poiypeptide
GB0917242D0 (en) * 2009-10-01 2009-11-18 Medical Res Council Acetyl lysine incorporation with tRNA synthetase
ES2623057T3 (es) 2010-04-15 2017-07-10 Medimmune Limited Pirrolobenzodiazepinas usadas para tratar enfermedades proliferativas
EP2563753B9 (en) * 2010-04-27 2016-07-06 SynAffix B.V. Fused cyclooctyne compounds and their use in metal-free click reactions
US20120077186A1 (en) 2010-05-07 2012-03-29 Oregon Health & Science University Use of cysteine-derived suppressor trnas for non-native amino acid incorporation
WO2011156686A2 (en) 2010-06-11 2011-12-15 The Regents Of The University Of Colorado, A Body Corporate Method for synthesizing a cyclic multivalent peptide using a thiol-mediated reaction
EP2670767B1 (en) 2011-02-03 2017-12-20 European Molecular Biology Laboratory Unnatural amino acids comprising a cyclooctynyl or trans-cyclooctenyl analog group and uses thereof
GB201110815D0 (en) * 2011-06-24 2011-08-10 Medical Res Council Incorporation of subtituted lysines into polypeptides
WO2013036748A1 (en) * 2011-09-09 2013-03-14 Berry, Lana, L. Bicyclo[6.1.0]non-4-yne reagents for chemical modification of oligonucleotides
GB201201100D0 (en) 2012-01-20 2012-03-07 Medical Res Council Polypeptides and methods
JP6343604B2 (ja) * 2012-05-18 2018-06-13 メディカル リサーチ カウンシル BCN基を含むアミノ酸をコードする直交性コドンと、直交性PylRS合成酵素とを使用して、BCN基を含むアミノ酸をポリペプチドに取り込む方法
ES2728864T3 (es) 2012-08-31 2019-10-29 Sutro Biopharma Inc Aminoácidos modificados que comprenden un grupo azido
CA2885796C (en) 2012-09-24 2022-05-03 Allozyne, Inc. Cell lines
GB2528227A (en) 2014-03-14 2016-01-20 Medical Res Council Cyclopropene amino acids and methods
GB201419109D0 (en) 2014-10-27 2014-12-10 Medical Res Council Incorporation of unnatural amino acids into proteins
US20180171321A1 (en) * 2015-03-27 2018-06-21 The University Of Queensland Platform for a non-natural amino acid incorporation into proteins
GB201817444D0 (en) 2018-10-26 2018-12-12 Res & Innovation Uk Methods and compositions
EP3868882A1 (en) * 2020-02-21 2021-08-25 European Molecular Biology Laboratory Archaeal pyrrolysyl trna synthetases for orthogonal use

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US20150148525A1 (en) 2015-05-28
CN108410827B (zh) 2023-05-09
HK1208704A1 (en) 2016-03-11
CA2873793A1 (en) 2013-11-21
US11732001B2 (en) 2023-08-22
IN2014DN09922A (enExample) 2015-08-14
CN108410827A (zh) 2018-08-17
CN104718285A (zh) 2015-06-17
WO2013171485A1 (en) 2013-11-21
EP2852664B1 (en) 2017-09-06
US20230340013A1 (en) 2023-10-26
CA2873793C (en) 2022-02-22
US20200271658A1 (en) 2020-08-27
BR112014028588A2 (pt) 2017-06-27
EP2852664A1 (en) 2015-04-01
BR112014028588A8 (pt) 2021-06-29
JP2015523965A (ja) 2015-08-20
BR112014028588B1 (pt) 2023-03-21

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