CN105593238B - 使用微生物转谷氨酰胺酶进行赖氨酸特异性化学酶法蛋白质修饰 - Google Patents

使用微生物转谷氨酰胺酶进行赖氨酸特异性化学酶法蛋白质修饰 Download PDF

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CN105593238B
CN105593238B CN201480046805.8A CN201480046805A CN105593238B CN 105593238 B CN105593238 B CN 105593238B CN 201480046805 A CN201480046805 A CN 201480046805A CN 105593238 B CN105593238 B CN 105593238B
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CN105593238A (zh
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艾梅·尤塞拉
扎卡里·鲁滨逊
珍妮弗·科布
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Novartis AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/101—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A61K47/6415—Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters 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
    • C07C271/22—Esters 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
    • C07D229/02—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms containing three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
    • C07K1/1075—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of amino acids or peptide residues
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/13—Labelling of peptides
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    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05—Dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/06—Tripeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/07—Tetrapeptides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane

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  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
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  • Biophysics (AREA)
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  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Gastroenterology & Hepatology (AREA)
CN201480046805.8A 2013-07-11 2014-07-11 使用微生物转谷氨酰胺酶进行赖氨酸特异性化学酶法蛋白质修饰 Active CN105593238B (zh)

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US201361845273P 2013-07-11 2013-07-11
US61/845,273 2013-07-11
US201462016044P 2014-06-23 2014-06-23
US62/016,044 2014-06-23
PCT/US2014/046409 WO2015006728A2 (en) 2013-07-11 2014-07-11 Site-specific chemoenzymatic protein modifications

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CN105593238B true CN105593238B (zh) 2020-09-08

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US (4) US9359400B2 (https=)
EP (2) EP3019515B1 (https=)
JP (1) JP6739333B2 (https=)
KR (1) KR20160040556A (https=)
CN (1) CN105593238B (https=)
AU (1) AU2014286990A1 (https=)
BR (1) BR112016000585A2 (https=)
CA (1) CA2918076A1 (https=)
EA (1) EA201690205A1 (https=)
ES (1) ES2756526T3 (https=)
MX (1) MX2016000393A (https=)
WO (1) WO2015006728A2 (https=)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2014286990A1 (en) 2013-07-11 2016-02-11 Novartis Ag Lysine-specific chemoenzymatic protein modifications using microbial transglutaminase
US10588980B2 (en) 2014-06-23 2020-03-17 Novartis Ag Fatty acids and their use in conjugation to biomolecules
UA124622C2 (uk) * 2015-12-18 2021-10-20 ЕЙСАЙ Ар ЕНД Ді МЕНЕДЖМЕНТ КО., ЛТД. Кон'юговані імуноглобуліни з c-кінцевим лізином
EP3436061A4 (en) 2016-03-31 2019-12-04 Liffey Biotech Limited Saccharide-polypeptide-conjugate compositions and methods of use thereof
MY202858A (en) * 2016-06-10 2024-05-25 Eisai R&D Man Co Ltd Lysine conjugated immunoglobulins
BR112019003992A2 (pt) 2016-09-02 2019-05-28 Sanofi Pasteur Inc vacina contra neisseria meningitidis
CN110366428B (zh) 2016-12-30 2024-05-17 Vaxcyte公司 具有非天然氨基酸的多肽-抗原缀合物
US11951165B2 (en) 2016-12-30 2024-04-09 Vaxcyte, Inc. Conjugated vaccine carrier proteins
WO2019070994A1 (en) 2017-10-04 2019-04-11 Liffey Biotech Limited SACCHARIDE-POLYPEPTIDE CONJUGATE COMPOSITIONS AND METHODS OF USE
CA3127824A1 (en) * 2019-01-25 2020-07-30 Avedro, Inc. Bis(diazirine) derivatives as photo-crossslinker for treating corneal ectatic disorders
CA3259278A1 (en) * 2022-06-16 2023-12-21 The General Hospital Corporation BICYCLONONYN REAGENTS FOR CELL IMAGING
CN119375471A (zh) * 2023-07-26 2025-01-28 菲鹏生物股份有限公司 抗体和抗体缀合物及其用途

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5543397A (en) * 1990-07-12 1996-08-06 Degussa Aktiengesellschaft New N-acyl dipeptides and their use
EP0815833A3 (en) * 1996-06-24 1998-05-27 Givaudan-Roure (International) S.A. Malodour preventing agents
WO2010002042A1 (ja) * 2008-07-04 2010-01-07 国立大学法人 九州大学 タンパク質ラベル化用酵素基質

Family Cites Families (53)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4179337A (en) 1973-07-20 1979-12-18 Davis Frank F Non-immunogenic polypeptides
JPH0665280B2 (ja) 1987-03-04 1994-08-24 味の素株式会社 タンパクゲル化剤及びそれを用いるタンパクのゲル化方法
JP2849773B2 (ja) 1990-08-27 1999-01-27 天野製薬株式会社 ストレプトミセス属由来のトランスグルタミナーゼの製造法
US5153312A (en) 1990-09-28 1992-10-06 American Cyanamid Company Oligosaccharide conjugate vaccines
PL175595B1 (pl) 1992-08-31 1999-01-29 North American Vaccine Inc Antygenowy/immunogenny koniugat do wytwarzania szczepionki przeciwko infekcji N.meningitidis, sposób wytwarzania antygenowego/immunogennego koniugatu oraz szczepionka przeciwko infekcji N.meningitidis
US5425946A (en) 1992-08-31 1995-06-20 North American Vaccine, Inc. Vaccines against group C Neisseria meningitidis
US5508191A (en) 1993-07-05 1996-04-16 Takeda Chemical Industries, Ltd. Mutant strains of agrobacterium for producing β-1,3-glucan
NZ291414A (en) 1994-08-26 1998-05-27 Novo Nordisk As Microbial transglutaminases and methods of production using fungi and dna constructs
EP0785276A4 (en) 1994-09-29 2002-01-09 Ajinomoto Kk MODIFICATION OF A PEPTIDE AND A PROTEIN
CA2208730A1 (en) 1995-01-19 1996-07-25 Novo Nordisk A/S Transglutaminases from oomycetes
JP3669390B2 (ja) 1995-02-09 2005-07-06 味の素株式会社 バチルス属細菌由来のトランスグルタミナーゼ
US6284884B1 (en) 1995-06-07 2001-09-04 North American Vaccine, Inc. Antigenic group B streptococcus type II and type III polysaccharide fragments having a 2,5-anhydro-D-mannose terminal structure and conjugate vaccine thereof
CN1231675A (zh) 1996-09-26 1999-10-13 味之素株式会社 修饰的生理活性蛋白及含有该蛋白的药物组合物
US6299881B1 (en) 1997-03-24 2001-10-09 Henry M. Jackson Foundation For The Advancement Of Military Medicine Uronium salts for activating hydroxyls, carboxyls, and polysaccharides, and conjugate vaccines, immunogens, and other useful immunological reagents produced using uronium salts
US6919076B1 (en) 1998-01-20 2005-07-19 Pericor Science, Inc. Conjugates of agents and transglutaminase substrate linking molecules
US6958148B1 (en) 1998-01-20 2005-10-25 Pericor Science, Inc. Linkage of agents to body tissue using microparticles and transglutaminase
WO1999036570A2 (en) 1998-01-20 1999-07-22 Pericor Science Inc Transglutaminase linkage of agents to tissue
US6936258B1 (en) 1999-03-19 2005-08-30 Nabi Biopharmaceuticals Staphylococcus antigen and vaccine
SI21352A (sl) 2001-01-23 2004-06-30 Aventis Pasteur Multivalentno meningokokno cepivo iz konjugata polisaharida-proteina
US7605175B2 (en) 2001-03-02 2009-10-20 Gpc Biotech Ag Inhibitors of cyclin-dependent kinases, compositions and uses related thereto
GB0115176D0 (en) 2001-06-20 2001-08-15 Chiron Spa Capular polysaccharide solubilisation and combination vaccines
JP2003199569A (ja) 2001-12-17 2003-07-15 Food Industry Research & Development Inst ストレプトベルティシリウム・ラダカヌムのトランスグルタミナーゼ遺伝子及び該遺伝子によってコードされるトランスグルタミナーゼ
ES2616180T3 (es) 2002-03-26 2017-06-09 Glaxosmithkline Biologicals Sa Sacáridos modificados con estabilidad mejorada en agua para su uso como medicamento
GB0211118D0 (en) 2002-05-15 2002-06-26 Polonelli Luciano Vaccines
GB0323103D0 (en) 2003-10-02 2003-11-05 Chiron Srl De-acetylated saccharides
US20080019918A1 (en) 2004-09-10 2008-01-24 Takao Aoki Medicinal Preparation
MX2007005202A (es) 2004-11-01 2007-07-09 Brigham & Womens Hospital Polisacaridos de estreptococo modificados y usos de los mismos.
GB0502096D0 (en) 2005-02-01 2005-03-09 Chiron Srl Purification of streptococcal capsular polysaccharide
MX2007015676A (es) * 2005-06-15 2008-02-20 Novo Nordisk Healthcare Ag Conjugacion de la hormona de crecimiento mediada por transglutaminasa.
GB0700562D0 (en) 2007-01-11 2007-02-21 Novartis Vaccines & Diagnostic Modified Saccharides
JP5703020B2 (ja) * 2007-08-24 2015-04-15 ノボ ノルディスク ヘルス ケア アーゲー タンパク質を選択的に修飾するための組成物と方法
US8426179B2 (en) * 2007-08-30 2013-04-23 Northwestern University Synthetic peptide and peptide conjugates and related tissue coupling methods via transglutaminase enzyme
DE102007044296A1 (de) * 2007-09-17 2009-03-19 Hans-Lothar Prof. Dr. Fuchsbauer Strukturmodulator von Proteinen
US8137925B2 (en) * 2007-11-09 2012-03-20 Massachusetts Institute Of Technology Methods and compositions for protein labeling using lipoic acid ligases
GB0818453D0 (en) 2008-10-08 2008-11-12 Novartis Ag Fermentation processes for cultivating streptococci and purification processes for obtaining cps therefrom
ES2401965T3 (es) * 2009-02-19 2013-04-25 Novo Nordisk A/S Modificación de Factor VIII
FR2947269B1 (fr) 2009-06-29 2013-01-18 Sanofi Aventis Nouveaux composes anticancereux
WO2011002852A2 (en) 2009-06-30 2011-01-06 The Regents Of The University Of Michigan Pro-drug complexes and related methods of use
US20110020837A1 (en) 2009-07-07 2011-01-27 Universiteit Utrecht Holding B.V. Method for isolating or identifying a target protein interacting with a lipid in a cell
CA2785410A1 (en) 2009-12-23 2011-06-30 Carlos F. Barbas, Iii Tyrosine bioconjugation through aqueous ene-like reactions
EP2563753B9 (en) 2010-04-27 2016-07-06 SynAffix B.V. Fused cyclooctyne compounds and their use in metal-free click reactions
EP2591354B1 (en) 2010-07-07 2016-09-07 Ardelyx, Inc. Compounds and methods for inhibiting phosphate transport
WO2012004419A2 (en) 2010-07-09 2012-01-12 Université De Bretagne Occidentale Modular construction of lipophospholipids
US9567346B2 (en) 2010-10-29 2017-02-14 Life Technologies Corporation Biotin derivatives
CA2813411C (en) 2010-11-05 2016-08-02 Rinat Neuroscience Corporation Engineered polypeptide conjugates and methods for making thereof using transglutaminase
CA2823837A1 (en) 2010-12-07 2012-06-14 Yale University Small-molecule hydrophobic tagging of fusion proteins and induced degradation of same
EP2651411B1 (en) 2010-12-13 2020-09-16 Immunomedics, Inc. Methods and compositions for improved f-18 labeling of proteins, peptides and other molecules
WO2012142659A1 (en) 2011-04-19 2012-10-26 Baker Idi Heart And Diabetes Institute Holdings Limited Site-selective modification of proteins
FR2981352B1 (fr) * 2011-10-17 2015-07-03 Centre Nat Rech Scient Procede de synthese de proteines
CN104145015A (zh) * 2011-12-01 2014-11-12 安吉奥开米公司 靶向的溶酶体酶化合物
JP5509440B2 (ja) * 2012-06-22 2014-06-04 国立大学法人九州大学 タンパク質−核酸複合体の製造方法および標的物の検出方法
CN105517577A (zh) * 2013-06-21 2016-04-20 先天制药公司 多肽的酶促偶联
AU2014286990A1 (en) 2013-07-11 2016-02-11 Novartis Ag Lysine-specific chemoenzymatic protein modifications using microbial transglutaminase

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5543397A (en) * 1990-07-12 1996-08-06 Degussa Aktiengesellschaft New N-acyl dipeptides and their use
EP0815833A3 (en) * 1996-06-24 1998-05-27 Givaudan-Roure (International) S.A. Malodour preventing agents
WO2010002042A1 (ja) * 2008-07-04 2010-01-07 国立大学法人 九州大学 タンパク質ラベル化用酵素基質

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Fluorescent substrates for covalent protein labeling catalyzed by microbial transglutaminase;N Kamiya;《Org. Biomol. Chem》;20090101;第7卷(第17期);全文 *
Langmuir monolayers of diacyl glycerol amino acid-based surfactants. Effect of the substitution pattern of the glycerol backbone;R Albalat;《Langmuir》;20031201;第19卷(第26期);全文 *
Modification of Different IgG1 Antibodies via Glutamine and Lysine using Bacterial and Human Tissue Transglutaminase;Thomas L. Mindt等;《Bioconjugate Chem》;20080101;第19卷(第1期);第271页摘要和第274页表1中化合物2 *
site-specific modification of proteins mediated by transglutaminase;Abhijeet Satwekar;《NATURE PRECEDINGS》;20110606;全文 *

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