AU2014286990A1 - Lysine-specific chemoenzymatic protein modifications using microbial transglutaminase - Google Patents

Lysine-specific chemoenzymatic protein modifications using microbial transglutaminase Download PDF

Info

Publication number
AU2014286990A1
AU2014286990A1 AU2014286990A AU2014286990A AU2014286990A1 AU 2014286990 A1 AU2014286990 A1 AU 2014286990A1 AU 2014286990 A AU2014286990 A AU 2014286990A AU 2014286990 A AU2014286990 A AU 2014286990A AU 2014286990 A1 AU2014286990 A1 AU 2014286990A1
Authority
AU
Australia
Prior art keywords
protein
pct
polysaccharide
linear
group
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.)
Abandoned
Application number
AU2014286990A
Other languages
English (en)
Inventor
Jennifer COBB
Zachary ROBINSON
Aimee USERA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of AU2014286990A1 publication Critical patent/AU2014286990A1/en
Assigned to NOVARTIS AG reassignment NOVARTIS AG Request for Assignment Assignors: COBB, Jennifer, ROBINSON, Zachary, USERA, Aimee
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • 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
    • C07D209/04—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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D257/08—Six-membered rings
    • 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
    • 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
    • C07K5/06008—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
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Analytical Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Immunology (AREA)
  • 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)
  • Gastroenterology & Hepatology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
AU2014286990A 2013-07-11 2014-07-11 Lysine-specific chemoenzymatic protein modifications using microbial transglutaminase Abandoned AU2014286990A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
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

Publications (1)

Publication Number Publication Date
AU2014286990A1 true AU2014286990A1 (en) 2016-02-11

Family

ID=51298955

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2014286990A Abandoned AU2014286990A1 (en) 2013-07-11 2014-07-11 Lysine-specific chemoenzymatic protein modifications using microbial transglutaminase

Country Status (12)

Country Link
US (4) US9359400B2 (enExample)
EP (2) EP3613755A1 (enExample)
JP (1) JP6739333B2 (enExample)
KR (1) KR20160040556A (enExample)
CN (1) CN105593238B (enExample)
AU (1) AU2014286990A1 (enExample)
BR (1) BR112016000585A2 (enExample)
CA (1) CA2918076A1 (enExample)
EA (1) EA201690205A1 (enExample)
ES (1) ES2756526T3 (enExample)
MX (1) MX2016000393A (enExample)
WO (1) WO2015006728A2 (enExample)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105593238B (zh) 2013-07-11 2020-09-08 诺华股份有限公司 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
US10588980B2 (en) 2014-06-23 2020-03-17 Novartis Ag Fatty acids and their use in conjugation to biomolecules
NZ742916A (en) * 2015-12-18 2023-03-31 Eisai R&D Man Co Ltd C-terminal lysine conjugated immunoglobulins
US11058757B2 (en) 2016-03-31 2021-07-13 Pogona, LLC Saccharide-polypeptide conjugate compositions and methods of use thereof
PE20190340A1 (es) * 2016-06-10 2019-03-07 Eisai Randd Man Co Ltd Inmunglobulinas conjugadas con lisina
KR20190044663A (ko) 2016-09-02 2019-04-30 사노피 파스퇴르 인크 네이세리아 메닌기티디스 백신
US11951165B2 (en) 2016-12-30 2024-04-09 Vaxcyte, Inc. Conjugated vaccine carrier proteins
KR20190103256A (ko) 2016-12-30 2019-09-04 수트로박스, 인코포레이티드 비자연 아미노산을 갖는 폴리펩타이드-항원 접합체
WO2019070994A1 (en) 2017-10-04 2019-04-11 Liffey Biotech Limited SACCHARIDE-POLYPEPTIDE CONJUGATE COMPOSITIONS AND METHODS OF USE
CN113811527B (zh) * 2019-01-25 2024-12-31 艾弗德罗股份有限公司 双(双吖丙啶)衍生物作为光交联剂治疗角膜扩张性疾病
WO2023244963A2 (en) * 2022-06-16 2023-12-21 The General Hospital Corporation Bicyclononyne reagents for cell imaging
WO2025020905A1 (zh) * 2023-07-26 2025-01-30 菲鹏生物股份有限公司 抗体和抗体缀合物及其用途

Family Cites Families (56)

* 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
DE4022267C2 (de) * 1990-07-12 1994-09-15 Degussa N-Acyldipeptide und deren Verwendung
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
US5425946A (en) 1992-08-31 1995-06-20 North American Vaccine, Inc. Vaccines against group C Neisseria meningitidis
WO1994005325A1 (en) 1992-08-31 1994-03-17 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
JP3720363B2 (ja) 1994-08-26 2005-11-24 ノボザイムス アクティーゼルスカブ 微生物のトランスグルタミナーゼ、それらの産生及び使用
US6010871A (en) 1994-09-29 2000-01-04 Ajinomoto Co., Inc. Modification of peptide and protein
ATE248219T1 (de) 1995-01-19 2003-09-15 Novozymes As Transglutaminasen aus oomyzeten
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
EP0815833B1 (en) * 1996-06-24 2003-04-09 Givaudan SA Malodour preventing agents
EP0950665A4 (en) 1996-09-26 2004-05-06 Ajinomoto Kk PHYSIOLOGICALLY ACTIVE MODIFIED PROTEINS AND DRUG COMPOSITIONS CONTAINING THEM
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
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
US6919076B1 (en) 1998-01-20 2005-07-19 Pericor Science, Inc. Conjugates of agents and transglutaminase substrate linking molecules
US6936258B1 (en) 1999-03-19 2005-08-30 Nabi Biopharmaceuticals Staphylococcus antigen and vaccine
JP2005504718A (ja) 2001-01-23 2005-02-17 アヴェンティス パストゥール 多価髄膜炎菌多糖−タンパク質複合ワクチン
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
MXPA04009339A (es) 2002-03-26 2005-01-25 Chiron Srl Sacaridos modificados que tienen estabilidad mejorada en agua.
GB0211118D0 (en) 2002-05-15 2002-06-26 Polonelli Luciano Vaccines
GB0323103D0 (en) 2003-10-02 2003-11-05 Chiron Srl De-acetylated saccharides
KR20070052747A (ko) 2004-09-10 2007-05-22 도레이 가부시끼가이샤 의약품제제
AU2005302269B2 (en) 2004-11-01 2011-05-19 The Brigham And Women's Hospital, Inc. Modified streptococcal polysaccharides and uses thereof
GB0502096D0 (en) 2005-02-01 2005-03-09 Chiron Srl Purification of streptococcal capsular polysaccharide
BRPI0611570A2 (pt) * 2005-06-15 2011-02-22 Novo Nordisk Healthcare Ag métodos para fixar covalentemente peg a um polipeptìdeo e para modificar propriedades farmacológicas de hormÈnio de crescimento, composto e sais, pró-drogas ou solvatos farmaceuticamente aceitáveis do mesmo, hormÈnio de crescimento humano, composição farmacêutica, método para tratamento de doença e, uso de um composto
GB0700562D0 (en) 2007-01-11 2007-02-21 Novartis Vaccines & Diagnostic Modified Saccharides
US8586532B2 (en) * 2007-08-24 2013-11-19 Novo Nordisk Healthcare A/G Method for selectively modifying a protein via transglutaminase catalyzed reaction
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
JPWO2010002042A1 (ja) * 2008-07-04 2011-12-22 国立大学法人九州大学 タンパク質ラベル化用酵素基質
CN102333788A (zh) * 2009-02-19 2012-01-25 诺沃—诺迪斯克有限公司 因子viii的修饰
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
ES2527536T7 (es) 2010-04-27 2016-03-08 Synaffix B.V. Compuestos de ciclooctina fusionada y su uso en reacciones clic sin metales
WO2012006475A1 (en) 2010-07-07 2012-01-12 Ardelyx, Inc. Compounds and methods for inhibiting phosphate transport
US20130178609A1 (en) 2010-07-09 2013-07-11 Centre National De La Recherche Scientifique - Cnrs Modular construction of lipophospholipids
EP2633062B1 (en) 2010-10-29 2017-12-27 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
EP2649099A4 (en) 2010-12-07 2016-10-19 Univ Yale SMALL MOLECULAR HYDROPHOBIC LABELING OF FUSION PROTEINS AND INDUCED REMOVAL FROM THIS
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
MX2014006594A (es) 2011-12-01 2015-09-16 Angiochem Inc Compuestos de enzimas lisosomales apuntados.
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
KR20160042871A (ko) * 2013-06-21 2016-04-20 이나뜨 파르마, 에스.아. 폴리펩티드의 효소적 콘쥬게이션
CN105593238B (zh) * 2013-07-11 2020-09-08 诺华股份有限公司 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

Also Published As

Publication number Publication date
EP3019515A2 (en) 2016-05-18
JP2016526574A (ja) 2016-09-05
MX2016000393A (es) 2016-10-26
CN105593238A (zh) 2016-05-18
CN105593238B (zh) 2020-09-08
CA2918076A1 (en) 2015-01-15
US20190300570A1 (en) 2019-10-03
US10975120B2 (en) 2021-04-13
US9359400B2 (en) 2016-06-07
US20160237116A1 (en) 2016-08-18
JP6739333B2 (ja) 2020-08-12
EA201690205A1 (ru) 2016-12-30
EP3019515B1 (en) 2019-08-21
WO2015006728A2 (en) 2015-01-15
BR112016000585A2 (pt) 2018-03-20
EP3613755A1 (en) 2020-02-26
WO2015006728A3 (en) 2015-03-12
US20150017192A1 (en) 2015-01-15
ES2756526T3 (es) 2020-04-27
US20220089639A1 (en) 2022-03-24
KR20160040556A (ko) 2016-04-14

Similar Documents

Publication Publication Date Title
US10975120B2 (en) Site-specific chemoenzymatic protein modifications
US10188719B2 (en) Conjugation of Streptococcal capsular saccharides
US12409231B2 (en) Cycloalkyne derivatized saccharides
CN104080479B (zh) 包括spr0096和spr2021抗原的运载体分子
BR112019013475A2 (pt) Conjugados de polipeptídeo-antígeno com aminoácidos não naturais
CN108064174A (zh) 抗原的载体分子
CA3094406C (en) Precision glycoconjugates as therapeutic tools
JP7100031B2 (ja) 免疫原性コンジュゲート及びその使用
CN110248681A (zh) nOMV-抗原缀合物及其用途
WO2020010016A1 (en) Self-adjuvanted immunogenic conjugates
US9144604B2 (en) Vaccine for Shigella
WO2012106251A2 (en) Pertussis vaccine
US10772946B2 (en) Immunogenic compositions against S. aureus
EA044044B1 (ru) Иммуногенные композиции, содержащие конъюгаты полипептид-антиген с неприродными аминокислотами

Legal Events

Date Code Title Description
PC1 Assignment before grant (sect. 113)

Owner name: NOVARTIS AG

Free format text: FORMER APPLICANT(S): ROBINSON, ZACHARY; USERA, AIMEE; COBB, JENNIFER

MK5 Application lapsed section 142(2)(e) - patent request and compl. specification not accepted