ATE329925T1 - Chemoselektive anknüpfung durch verwendung eines phosphins - Google Patents

Chemoselektive anknüpfung durch verwendung eines phosphins

Info

Publication number
ATE329925T1
ATE329925T1 AT01957599T AT01957599T ATE329925T1 AT E329925 T1 ATE329925 T1 AT E329925T1 AT 01957599 T AT01957599 T AT 01957599T AT 01957599 T AT01957599 T AT 01957599T AT E329925 T1 ATE329925 T1 AT E329925T1
Authority
AT
Austria
Prior art keywords
phosphine
final product
amide bond
engineered
reaction
Prior art date
Application number
AT01957599T
Other languages
English (en)
Inventor
Carolyn Bertozzi
Eliana Saxon
Original Assignee
Univ California
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 Univ California filed Critical Univ California
Application granted granted Critical
Publication of ATE329925T1 publication Critical patent/ATE329925T1/de

Links

Classifications

    • 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
    • C07K1/1077—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 residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
    • C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
    • C07H7/02—Acyclic radicals
    • 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
    • C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
    • C07K1/023—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution using racemisation inhibiting agents
    • 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
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AT01957599T 2000-03-16 2001-03-16 Chemoselektive anknüpfung durch verwendung eines phosphins ATE329925T1 (de)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18983700P 2000-03-16 2000-03-16

Publications (1)

Publication Number Publication Date
ATE329925T1 true ATE329925T1 (de) 2006-07-15

Family

ID=22698968

Family Applications (1)

Application Number Title Priority Date Filing Date
AT01957599T ATE329925T1 (de) 2000-03-16 2001-03-16 Chemoselektive anknüpfung durch verwendung eines phosphins

Country Status (6)

Country Link
US (7) US6570040B2 (de)
EP (1) EP1263771B1 (de)
AT (1) ATE329925T1 (de)
AU (1) AU2001281463A1 (de)
DE (1) DE60120650T2 (de)
WO (1) WO2001068565A2 (de)

Families Citing this family (125)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE329925T1 (de) * 2000-03-16 2006-07-15 Univ California Chemoselektive anknüpfung durch verwendung eines phosphins
US7256259B2 (en) 2000-05-12 2007-08-14 Wisconsin Alumni Research Foundation Methods for ligation of molecules to surfaces
US6972320B2 (en) 2000-05-12 2005-12-06 Wisconsin Alumni Research Foundation Ligation method and reagents to form an amide bond
US7173003B2 (en) * 2001-10-10 2007-02-06 Neose Technologies, Inc. Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF
US7795210B2 (en) * 2001-10-10 2010-09-14 Novo Nordisk A/S Protein remodeling methods and proteins/peptides produced by the methods
US7214660B2 (en) 2001-10-10 2007-05-08 Neose Technologies, Inc. Erythropoietin: remodeling and glycoconjugation of erythropoietin
US7157277B2 (en) 2001-11-28 2007-01-02 Neose Technologies, Inc. Factor VIII remodeling and glycoconjugation of Factor VIII
US8008252B2 (en) 2001-10-10 2011-08-30 Novo Nordisk A/S Factor VII: remodeling and glycoconjugation of Factor VII
ES2286386T3 (es) 2002-03-28 2007-12-01 Unilever N.V. Dulce de hielo congelado.
EP1534718A4 (de) * 2002-06-07 2006-06-07 Wisconsin Alumni Res Found Chemische synthese von reagenzien für die peptidkupplung
MXPA04012496A (es) * 2002-06-21 2005-09-12 Novo Nordisk Healthcare Ag Glicoformos del factor vii pegilados.
US20050233473A1 (en) * 2002-08-16 2005-10-20 Zyomyx, Inc. Methods and reagents for surface functionalization
AU2004221824B2 (en) * 2003-03-14 2009-08-27 Ratiopharm Gmbh Branched water-soluble polymers and their conjugates
US20040235027A1 (en) * 2003-03-31 2004-11-25 Regent Of The University Of California Preparation and application of ligand-biopolymer conjugates
SG155777A1 (en) 2003-04-09 2009-10-29 Neose Technologies Inc Glycopegylation methods and proteins/peptides produced by the methods
US8791070B2 (en) 2003-04-09 2014-07-29 Novo Nordisk A/S Glycopegylated factor IX
JP2007523630A (ja) * 2003-05-09 2007-08-23 ネオス テクノロジーズ インコーポレイテッド ヒト成長ホルモングリコシル化突然変異体の組成と調合法
US9005625B2 (en) * 2003-07-25 2015-04-14 Novo Nordisk A/S Antibody toxin conjugates
US7534902B2 (en) * 2003-11-14 2009-05-19 Wisconsin Alumni Research Foundation Fluorescence assays with improved sensitivity
US7070941B2 (en) * 2003-11-17 2006-07-04 Board Of Regents, The University Of Texas System Methods and compositions for tagging via azido substrates
US20080305992A1 (en) * 2003-11-24 2008-12-11 Neose Technologies, Inc. Glycopegylated erythropoietin
US8633157B2 (en) * 2003-11-24 2014-01-21 Novo Nordisk A/S Glycopegylated erythropoietin
US20070254834A1 (en) * 2003-11-24 2007-11-01 Defrees Shawn Glycopegylated Erythropoietin
US7956032B2 (en) 2003-12-03 2011-06-07 Novo Nordisk A/S Glycopegylated granulocyte colony stimulating factor
US20060040856A1 (en) 2003-12-03 2006-02-23 Neose Technologies, Inc. Glycopegylated factor IX
MXPA06006029A (es) * 2003-12-03 2006-08-23 Neose Technologies Inc Factor de estimulacion de colonias de granulocitos modificado por glicopolietilenglicol.
ES2560657T3 (es) * 2004-01-08 2016-02-22 Ratiopharm Gmbh Glicosilación con unión en O de péptidos G-CSF
WO2006010143A2 (en) 2004-07-13 2006-01-26 Neose Technologies, Inc. Branched peg remodeling and glycosylation of glucagon-like peptide-1 [glp-1]
US20090292110A1 (en) * 2004-07-23 2009-11-26 Defrees Shawn Enzymatic modification of glycopeptides
WO2006021553A1 (en) * 2004-08-23 2006-03-02 Covalys Biosciences Ag Method for protein purification and labeling based on a chemoselective reaction
EP1799249A2 (de) * 2004-09-10 2007-06-27 Neose Technologies, Inc. Glycopegyliertes interferon alpha
EP1799278A2 (de) 2004-09-28 2007-06-27 Baylor University Räumlich definierte modifikation frischen gewebes mithilfe kovalenter chemie
JP2008515915A (ja) * 2004-10-07 2008-05-15 エモリー ユニバーシティー 多機能性ナノ粒子結合体およびそれらの使用
EP1809339A2 (de) * 2004-10-07 2007-07-25 Koninklijke Philips Electronics N.V. Verbindungen, kits und verfahren zur verwendung in der medizinischen bilddarstellung
PL2586456T3 (pl) 2004-10-29 2016-07-29 Ratiopharm Gmbh Remodeling i glikopegilacja czynnika wzrostu fibroblastów (FGF)
WO2006069203A2 (en) 2004-12-22 2006-06-29 California Institute Of Technology Methods for proteomic profiling using non-natural amino acids
JP2008526864A (ja) * 2005-01-06 2008-07-24 ネオス テクノロジーズ インコーポレイテッド 糖断片を用いる糖結合
US9029331B2 (en) * 2005-01-10 2015-05-12 Novo Nordisk A/S Glycopegylated granulocyte colony stimulating factor
WO2006079364A1 (en) * 2005-01-31 2006-08-03 Stichting Voor De Technische Wetenschappen Specific and mild peptide or amide bond cleavage
EP1871795A4 (de) 2005-04-08 2010-03-31 Biogenerix Ag Zusammensetzungen und verfahren zur herstellung von glycosylierungsmutanten eines proteaseresistenten menschlichen wachstumshormons
GB0507123D0 (en) * 2005-04-08 2005-05-11 Isis Innovation Method
EP1891231A4 (de) 2005-05-25 2011-06-22 Novo Nordisk As Glykopegylierter faktor ix
US20110003744A1 (en) * 2005-05-25 2011-01-06 Novo Nordisk A/S Glycopegylated Erythropoietin Formulations
WO2006127910A2 (en) * 2005-05-25 2006-11-30 Neose Technologies, Inc. Glycopegylated erythropoietin formulations
US20070105755A1 (en) 2005-10-26 2007-05-10 Neose Technologies, Inc. One pot desialylation and glycopegylation of therapeutic peptides
WO2007030521A1 (en) * 2005-09-06 2007-03-15 Invitrogen Corporation Control of chemical modification
JP2009512641A (ja) * 2005-10-04 2009-03-26 コーニンクレッカ フィリップス エレクトロニクス エヌ ヴィ ［３＋２］アジド−アルキン環付加を使用するターゲットにされたイメージング及び／又は治療
WO2007039864A2 (en) * 2005-10-04 2007-04-12 Koninklijke Philips Electronics N.V. The staudinger reaction in imaging and therapy and kits for use in imaging and therapy
WO2007047668A2 (en) * 2005-10-14 2007-04-26 California Institute Of Technology Use of non-canonical amino acids as metabolic markers for rapidly-dividing cells
WO2007120192A2 (en) * 2005-10-27 2007-10-25 The President And Fellows Of Harvard College Methods and compositions for labeling nucleic acids
WO2007056191A2 (en) 2005-11-03 2007-05-18 Neose Technologies, Inc. Nucleotide sugar purification using membranes
US7465544B2 (en) * 2006-01-11 2008-12-16 Wisconsin Alumni Research Foundation Synthetic cofactor analogs of S-adenosylmethionine as ligatable probes of biological methylation and methods for their use
US8114636B2 (en) 2006-02-10 2012-02-14 Life Technologies Corporation Labeling and detection of nucleic acids
EP1987068B1 (de) * 2006-02-10 2018-08-08 Life Technologies Corporation Modifizierung von oligosacchariden und etikettierung von proteinen
KR101360637B1 (ko) * 2006-02-21 2014-02-07 헌트스만 인터내셔날, 엘엘씨 폴리이소시아누레이트 복합재의 제조 방법
WO2007111952A2 (en) * 2006-03-22 2007-10-04 The Scripps Research Institute Method of preparing glycopeptides
RU2008142542A (ru) * 2006-03-28 2010-05-10 Конинклейке Филипс Электроникс Н.В. (Nl) Применение лигирования штаудингера при сборке in vivo биологически активного соединения
US20080248959A1 (en) * 2006-07-21 2008-10-09 Neose Technologies, Inc. Glycosylation of peptides via o-linked glycosylation sequences
US7985783B2 (en) 2006-09-21 2011-07-26 The Regents Of The University Of California Aldehyde tags, uses thereof in site-specific protein modification
JP2010505874A (ja) 2006-10-03 2010-02-25 ノヴォ ノルディスク アー／エス ポリペプチドコンジュゲートの精製方法
MX2009003470A (es) * 2006-10-04 2009-04-14 Novo Nordisk As Azucares y glicopeptidos pegilados enlazados a glicerol.
FI20075030A0 (fi) * 2007-01-18 2007-01-18 Suomen Punainen Risti Veripalv Menetelmä solujen modifioimiseksi
BRPI0809670A8 (pt) * 2007-04-03 2018-12-18 Biogenerix Ag métodos para aumentar a produção de célula tronco, para aumentar o número de granulócitos em um indivíduo, para prevenir, tratar e aliviar a mielossupressão que resulta de uma terapia contra o câncer, para tratar uma condição em um indivíduo, para tratar neutropenia e trombocitopenia em um mamífero, para expandir células tronco hematopoiéticas em cultura, para aumentar a hematopoiese em um indivíduo, para aumentar o número de célulars progenitoras hematopoiéticas em um indivíduo, e para fornecer enxerto estável da medula óssea, e, forma de dosagem oral.
EP2162535A4 (de) * 2007-06-04 2011-02-23 Novo Nordisk As O-verknüpfte glykosylierung unter verwendung von n-acetylglucosaminyl-transferasen
MX2009013259A (es) 2007-06-12 2010-01-25 Novo Nordisk As Proceso mejorado para la produccion de azucares de nucleotidos.
US7968811B2 (en) * 2007-06-29 2011-06-28 Harley-Davidson Motor Company Group, Inc. Integrated ignition and key switch
US8207112B2 (en) * 2007-08-29 2012-06-26 Biogenerix Ag Liquid formulation of G-CSF conjugate
WO2009089396A2 (en) * 2008-01-08 2009-07-16 Neose Technologies, Inc. Glycoconjugation of polypeptides using oligosaccharyltransferases
ES2476690T3 (es) 2008-02-27 2014-07-15 Novo Nordisk A/S Moléculas conjugadas del Factor VIII
US8034396B2 (en) * 2008-04-01 2011-10-11 Tyco Healthcare Group Lp Bioadhesive composition formed using click chemistry
WO2009140541A2 (en) 2008-05-16 2009-11-19 Life Technologies Corporation Dual labeling methods for measuring cellular proliferation
US8350014B2 (en) * 2008-11-17 2013-01-08 Wisconsin Alumni Research Foundation Preparation of diazo and diazonium compounds
WO2010096394A2 (en) 2009-02-17 2010-08-26 Redwood Biosciences, Inc. Aldehyde-tagged protein-based drug carriers and methods of use
US9039979B2 (en) 2009-02-21 2015-05-26 Sofradim Production Apparatus and method of reacting polymers passing through metal ion chelated resin matrix to produce injectable medical devices
US8956603B2 (en) 2009-02-21 2015-02-17 Sofradim Production Amphiphilic compounds and self-assembling compositions made therefrom
EP2398523B1 (de) 2009-02-21 2018-04-04 Covidien LP Medizinische vorrichtungen mit aktivierten oberflächen
US9523159B2 (en) 2009-02-21 2016-12-20 Covidien Lp Crosslinked fibers and method of making same using UV radiation
AU2010215200A1 (en) 2009-02-21 2011-10-13 Sofradim Production Apparatus and method of reaching polymers by exposure to UV radiation to produce injectable medical devices
CA2753165A1 (en) 2009-02-21 2010-08-26 Sofradim Production Compounds and medical devices activated with solvophobic linkers
US8512728B2 (en) 2009-02-21 2013-08-20 Sofradim Production Method of forming a medical device on biological tissue
AU2010215936B2 (en) 2009-02-21 2015-03-05 Covidien Lp Medical devices having activated surfaces
CA2753173C (en) 2009-02-21 2017-05-30 Sofradim Production Medical devices with an activated coating
US8877170B2 (en) * 2009-02-21 2014-11-04 Sofradim Production Medical device with inflammatory response-reducing coating
US8663689B2 (en) * 2009-02-21 2014-03-04 Sofradim Production Functionalized adhesive medical gel
US8968733B2 (en) * 2009-02-21 2015-03-03 Sofradim Production Functionalized surgical adhesives
US8535477B2 (en) * 2009-02-21 2013-09-17 Sofradim Production Medical devices incorporating functional adhesives
AU2010215196B2 (en) 2009-02-21 2015-04-16 Covidien Lp Crosslinked fibers and method of making same by extrusion
DE102009012640A1 (de) 2009-03-09 2010-09-30 Freie Universität Berlin Mit einer Phosphoamidatgruppe modifizierte Verbindung und deren Verwendung
WO2011045418A1 (en) * 2009-10-16 2011-04-21 Dsm Ip Assets B.V. Azido alkanoic acids and derivatives thereof in feed for reducing methane formation emanating from the digestive activities of ruminants
FR2952058B1 (fr) 2009-10-29 2013-10-04 Centre Nat Rech Scient Procede de ligation native de polypeptides
CA2794336A1 (en) 2010-03-25 2011-09-29 Sofradim Production Surgical fasteners and methods for sealing wounds
CA2794335A1 (en) 2010-03-25 2011-09-29 Sofradim Production Medical devices incorporating functional adhesives
WO2012006147A1 (en) 2010-06-29 2012-01-12 Tyco Healthcare Group Lp Microwave-powered reactor and method for in situ forming implants
CA2804251A1 (en) 2010-07-01 2012-01-05 Sofradim Production Medical device with predefined activated cellular integration
WO2012014080A2 (en) 2010-07-27 2012-02-02 Sofradim Production Polymeric fibers having tissue reactive members
AU2012205301B2 (en) 2011-01-14 2017-01-05 Redwood Bioscience, Inc. Aldehyde-tagged immunoglobulin polypeptides and method of use thereof
FR2971509B1 (fr) 2011-02-16 2013-02-22 Centre Nat Rech Scient Procede de preparation de peptides par assemblage de multiples fragments peptidiques
EP2966061B1 (de) 2011-03-04 2017-05-03 Life Technologies Corporation Verbindungen und verfahren zur konjugation von biomolekülen
WO2012134925A1 (en) 2011-03-25 2012-10-04 Life Technologies Corporation Heterobifunctional esters for use in labeling target molecules
US20140170653A1 (en) 2011-04-15 2014-06-19 Life Technologies Corporation Chemical ligation
US9556195B2 (en) 2011-09-12 2017-01-31 The Regents Of The University Of California Compositions and methods for quadricyclane modification of biomolecules
FR2981352B1 (fr) 2011-10-17 2015-07-03 Centre Nat Rech Scient Procede de synthese de proteines
FR2988392B1 (fr) 2012-03-21 2014-04-11 Centre Nat Rech Scient Procede de ligation native
CN104704359A (zh) 2012-10-25 2015-06-10 生命科技公司 糖蛋白酶介导位点特异性放射性标记的方法和组合物
WO2014074218A1 (en) 2012-11-12 2014-05-15 Redwood Bioscience, Inc. Compounds and methods for producing a conjugate
US9775928B2 (en) 2013-06-18 2017-10-03 Covidien Lp Adhesive barbed filament
WO2015081282A1 (en) 2013-11-27 2015-06-04 Redwood Bioscience, Inc. Hydrazinyl-pyrrolo compounds and methods for producing a conjugate
DE102013113156A1 (de) * 2013-11-28 2015-05-28 Freie Universität Berlin Verbindung und Verfahren zur selektiven Radiomarkierung von Polypeptiden mittels Festphasensynthese
US9410958B2 (en) 2014-03-25 2016-08-09 The Regents Of The University Of California Alkyne-activated fluorogenic azide compounds and methods of use thereof
WO2017027337A1 (en) * 2015-08-13 2017-02-16 The Regents Of The University Of California Bioorthogonal reaction of an amine n-oxide and a boron agent
IL259186B2 (en) 2015-11-09 2023-03-01 Scherer Technologies Llc R P Anti-cd22-maytensin antibody conjugates and methods of using them
US10195283B2 (en) 2016-03-18 2019-02-05 R.P. Scherer Technologies, Llc Hydrazinyl-substituted heteroaryl compounds and methods for producing a conjugate
CA3019398A1 (en) 2016-04-26 2017-11-02 R.P. Scherer Technologies, Llc Antibody conjugates and methods of making and using the same
WO2017218891A1 (en) 2016-06-17 2017-12-21 Life Technologies Corporation Site-specific crosslinking of antibodies
US10814036B2 (en) 2016-11-07 2020-10-27 Baylor University Drug-eluting live tissue for transplantation
CA3049449A1 (en) 2017-01-18 2018-07-26 Visterra, Inc. Antibody molecule-drug conjugates and uses thereof
CN111065623B9 (zh) 2017-05-24 2024-10-25 德克萨斯州大学系统董事会 用于抗体药物缀合物的接头
SG11202102801TA (en) 2019-04-29 2021-04-29 Illumina Inc Identification and analysis of microbial samples by rapid incubation and nucleic acid enrichment
AU2021248643A1 (en) 2020-04-03 2022-10-27 Visterra, Inc. Antibody molecule-drug conjugates and uses thereof
MX2023005979A (es) 2020-11-20 2023-08-11 Scherer Technologies Llc R P Enlazadores de escisión doble de glicósido para conjugados de anticuerpo y fármaco.
CA3221222A1 (en) 2021-05-27 2022-12-01 R.P. Scherer Technologies, Llc Methods of controlling cleavage of formylglycine-containing polypeptides
EP4108669A1 (de) * 2021-06-24 2022-12-28 Institute Of Organic Chemistry And Biochemistry As CR, V.V.I. Kohlenhydratderivate und kits zur zelloberflächenmarkierung
US11879010B2 (en) 2021-09-30 2024-01-23 The Charlotte Mecklenburg Hospital Authority Methods and compositions for pretargeted immunotherapy
CN116102612A (zh) * 2021-11-09 2023-05-12 香港城市大学深圳研究院 一种细胞表面蛋白的分离纯化方法及应用
CN117736135B (zh) * 2024-02-19 2024-05-07 西北农林科技大学深圳研究院 一种蛋白质位点特异性修饰的方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4321366A (en) * 1978-05-12 1982-03-23 Research Corporation Process of preparing 2-azido-2-deoxyarabinofuranosyl halides
US4292437A (en) * 1979-06-27 1981-09-29 E. I. Du Pont De Nemours And Company Preparation of isobutyric acid and esters
EP0403524B1 (de) * 1988-03-09 1993-02-10 Cis Bio International Herstellung von als radiopharmazeutische produkte verwendbare nitruroverbindungen
DE4325816A1 (de) 1993-07-31 1995-02-02 Hoechst Ag Sekundäre und tertiäre Phosphane und Verfahren zu ihrer Herstellung
US5874628A (en) * 1997-03-26 1999-02-23 Monsanto Company Method for preparation of tertiary phosphines via nickel-catalyzed cross coupling
ATE329925T1 (de) 2000-03-16 2006-07-15 Univ California Chemoselektive anknüpfung durch verwendung eines phosphins
US6972320B2 (en) 2000-05-12 2005-12-06 Wisconsin Alumni Research Foundation Ligation method and reagents to form an amide bond

Also Published As

Publication number Publication date
US7122703B2 (en) 2006-10-17
AU2001281463A1 (en) 2001-09-24
US7923582B2 (en) 2011-04-12
US20070037964A1 (en) 2007-02-15
US20030199084A1 (en) 2003-10-23
US7939626B2 (en) 2011-05-10
DE60120650T2 (de) 2007-05-31
EP1263771A2 (de) 2002-12-11
EP1263771B1 (de) 2006-06-14
US20020016003A1 (en) 2002-02-07
US8076496B2 (en) 2011-12-13
US7838665B2 (en) 2010-11-23
US20050148032A1 (en) 2005-07-07
US6570040B2 (en) 2003-05-27
DE60120650D1 (de) 2006-07-27
US20060276658A1 (en) 2006-12-07
US7667012B2 (en) 2010-02-23
US20080214801A1 (en) 2008-09-04
WO2001068565A3 (en) 2002-05-23
US20110236930A1 (en) 2011-09-29
WO2001068565A2 (en) 2001-09-20

Similar Documents

Publication Publication Date Title
ATE329925T1 (de) Chemoselektive anknüpfung durch verwendung eines phosphins
WO2006050262A3 (en) Compositions and methods for modification of biomolecules
Grandjean et al. On the preparation of carbohydrate− protein conjugates using the traceless Staudinger ligation
US7919454B2 (en) Methods of treating using conjugates transported by a PEPT2 transporter
WO2007107587A3 (en) Cholesterol lowering protein hydrolysates
AR045450A1 (es) Conjugados de almidon de hidroxialquilo y una proteina
WO2005058958A3 (en) Novel glp-1 analogues linked to albumin-like agents
JPS61191675A (ja) 巨大分子物質
CA2473802A1 (en) Engineering absorption of therapeutic compounds via colonic transporters
WO2005039641A3 (en) Biomacromolecule polymer conjugates
ATE293125T1 (de) Ligationsverfahren und reagenzien zur bildung einer amid-bindung
SG170022A1 (en) Method for production of peptide thioester compound
DE502004007479D1 (de) Verfahren zur Herstellung von 9,10-Dihydro-9-oxa-10-organyl-phosphaphenanthren-10-oxid und Derivaten desselben
NO20075829L (no) Syntese
WO2004011424A3 (en) Side chain anchored thioester and selenoester generators
MX2022007034A (es) Un metodo para formar un conjugado de una sulfonamida y un polipeptido.
US5871954A (en) Fatty acid analog enzyme substrates
Bonnet et al. Synthesis by chemoselective ligation and biological evaluation of novel cell-permeable PKC-ζ pseudosubstrate lipopeptides
Singh et al. A novel heterobifunctional linker for facile access to bioconjugates
FR2864534B1 (fr) Synthese d'acylurees et composition comportant des acylurees
JP2013177378A (ja) 芳香族アミノ基を有する非天然アミノ酸を導入したタンパク質の部位特異的な修飾方法
WO2006018164A3 (de) Fluoreszenzbasierende kinetische bestimmung der aktivität von transglutaminasen
WO2003018523A1 (en) Process for producing optically active halopropanediol derivative
WO2024064752A3 (en) Compositions of wet adhesives derived from vibrio cholerae biofilm adhesins and methods thereof
TW200505945A (en) Oligopeptides

Legal Events

Date Code Title Description
RER Ceased as to paragraph 5 lit. 3 law introducing patent treaties