WO2001068565A2 - Chemoselective ligation by use of a phosphine - Google Patents

Chemoselective ligation by use of a phosphine Download PDF

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Publication number
WO2001068565A2
WO2001068565A2 PCT/US2001/008546 US0108546W WO0168565A2 WO 2001068565 A2 WO2001068565 A2 WO 2001068565A2 US 0108546 W US0108546 W US 0108546W WO 0168565 A2 WO0168565 A2 WO 0168565A2
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WO
WIPO (PCT)
Prior art keywords
group
molecule
ester
aryl
compound
Prior art date
Application number
PCT/US2001/008546
Other languages
English (en)
French (fr)
Other versions
WO2001068565A3 (en
Inventor
Carolyn Bertozzi
Eliana Saxon
Original Assignee
The Regents Of The University Of 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 The Regents Of The University Of California filed Critical The Regents Of The University Of California
Priority to DE60120650T priority Critical patent/DE60120650T2/de
Priority to EP01957599A priority patent/EP1263771B1/en
Priority to AU2001281463A priority patent/AU2001281463A1/en
Publication of WO2001068565A2 publication Critical patent/WO2001068565A2/en
Publication of WO2001068565A3 publication Critical patent/WO2001068565A3/en

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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
    • C07K1/1077—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 System
    • 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 System
    • 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 System
    • 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 System
    • 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
PCT/US2001/008546 2000-03-16 2001-03-16 Chemoselective ligation by use of a phosphine WO2001068565A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE60120650T DE60120650T2 (de) 2000-03-16 2001-03-16 Chemoselektive anknüpfung durch verwendung eines phosphins
EP01957599A EP1263771B1 (en) 2000-03-16 2001-03-16 Chemoselective ligation by use of a phosphine
AU2001281463A AU2001281463A1 (en) 2000-03-16 2001-03-16 Chemoselective ligation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US18983700P 2000-03-16 2000-03-16
US60/189,837 2000-03-16

Publications (2)

Publication Number Publication Date
WO2001068565A2 true WO2001068565A2 (en) 2001-09-20
WO2001068565A3 WO2001068565A3 (en) 2002-05-23

Family

ID=22698968

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/008546 WO2001068565A2 (en) 2000-03-16 2001-03-16 Chemoselective ligation by use of a phosphine

Country Status (6)

Country Link
US (7) US6570040B2 (US07122703-20061017-C00006.png)
EP (1) EP1263771B1 (US07122703-20061017-C00006.png)
AT (1) ATE329925T1 (US07122703-20061017-C00006.png)
AU (1) AU2001281463A1 (US07122703-20061017-C00006.png)
DE (1) DE60120650T2 (US07122703-20061017-C00006.png)
WO (1) WO2001068565A2 (US07122703-20061017-C00006.png)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003104243A1 (en) 2002-06-07 2003-12-18 Wisconsin Alumni Research Foundation Chemical synthesis of reagents for peptide coupling
US6972320B2 (en) 2000-05-12 2005-12-06 Wisconsin Alumni Research Foundation Ligation method and reagents to form an amide bond
WO2006021553A1 (en) * 2004-08-23 2006-03-02 Covalys Biosciences Ag Method for protein purification and labeling based on a chemoselective reaction
WO2006038185A2 (en) * 2004-10-07 2006-04-13 Koninklijke Philips Electronics N.V. Use of the staudinger ligation in imaging and therapy end kits for imaging and therapy
US7256259B2 (en) 2000-05-12 2007-08-14 Wisconsin Alumni Research Foundation Methods for ligation of molecules to surfaces
WO2007110811A2 (en) * 2006-03-28 2007-10-04 Koninklijke Philips Electronics N.V. Use of the staudinger ligation in in vivo assembly of a biologically active compound
US7435435B2 (en) 2002-03-28 2008-10-14 Good Humor - Breyers Ice Cream, Division Of Conopco, Inc. Frozen ice confection
WO2007039864A3 (en) * 2005-10-04 2008-11-27 Koninkl Philips Electronics Nv The staudinger reaction in imaging and therapy and kits for use in imaging and therapy
WO2008029281A3 (en) * 2006-02-10 2009-09-11 Invitrogen Corporation Labeling and detection of post translationally modified proteins
WO2010102997A2 (de) 2009-03-09 2010-09-16 Freie Universität Berlin Mit einer phosphoramidat- und/oder phosphonamidgruppe modifizierte verbindung und deren verwendung
EP2118273A4 (en) * 2007-01-18 2011-01-12 Suomen Punainen Risti Veripalvelu METHOD OF MODIFYING CELLS
WO2011051906A1 (fr) 2009-10-29 2011-05-05 Centre National De La Recherche Scientifique (Cnrs) Procede de ligation native de polypeptides
US8076292B2 (en) 2001-10-10 2011-12-13 Novo Nordisk A/S Factor VIII: remodeling and glycoconjugation of factor VIII
US8114636B2 (en) 2006-02-10 2012-02-14 Life Technologies Corporation Labeling and detection of nucleic acids
WO2012110536A1 (fr) 2011-02-16 2012-08-23 Centre National De La Recherche Scientifique Procede de preparation de peptides par assemblage de multiples fragments peptidiques
WO2012142003A2 (en) 2011-04-15 2012-10-18 Life Technologies Corporation Chemical ligation
US8404809B2 (en) 2005-05-25 2013-03-26 Novo Nordisk A/S Glycopegylated factor IX
WO2013057084A1 (fr) 2011-10-17 2013-04-25 Centre National De La Recherche Scientifique (Cnrs) Procede de synthese de proteines
WO2013139719A1 (fr) 2012-03-21 2013-09-26 Centre National De La Recherche Scientifique (Cnrs) Procede de ligation native
US8632770B2 (en) 2003-12-03 2014-01-21 Novo Nordisk A/S Glycopegylated factor IX
US8791070B2 (en) 2003-04-09 2014-07-29 Novo Nordisk A/S Glycopegylated factor IX
US8865857B2 (en) 2010-07-01 2014-10-21 Sofradim Production Medical device with predefined activated cellular integration
WO2015078880A1 (de) * 2013-11-28 2015-06-04 Freie Universitaet Berlin Verbindung und verfahren zur selektiven radiomarkierung von polypeptiden mittels festphasensynthese
US9247931B2 (en) 2010-06-29 2016-02-02 Covidien Lp Microwave-powered reactor and method for in situ forming implants
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
US9493499B2 (en) 2007-06-12 2016-11-15 Novo Nordisk A/S Process for the production of purified cytidinemonophosphate-sialic acid-polyalkylene oxide (CMP-SA-PEG) as modified nucleotide sugars via anion exchange chromatography
US9510810B2 (en) 2009-02-21 2016-12-06 Sofradim Production Medical devices incorporating functional adhesives
US9775928B2 (en) 2013-06-18 2017-10-03 Covidien Lp Adhesive barbed filament

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1263771B1 (en) * 2000-03-16 2006-06-14 The Regents Of The University Of California Chemoselective ligation by use of a phosphine
US7173003B2 (en) * 2001-10-10 2007-02-06 Neose Technologies, Inc. Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF
US8008252B2 (en) 2001-10-10 2011-08-30 Novo Nordisk A/S Factor VII: remodeling and glycoconjugation of Factor VII
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
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
CA2519092C (en) * 2003-03-14 2014-08-05 Neose Technologies, Inc. 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
PL1615945T3 (pl) 2003-04-09 2012-03-30 Ratiopharm Gmbh Sposoby glikopegylacji i białka/peptydy wytwarzane tymi sposobami
BRPI0410164A (pt) * 2003-05-09 2006-05-16 Neose Technologies Inc composições e métodos para preparação de mutantes de glicosilação de hormÈnio do crescimento humano
US9005625B2 (en) * 2003-07-25 2015-04-14 Novo Nordisk A/S Antibody toxin conjugates
WO2005047245A2 (en) * 2003-11-14 2005-05-26 Wisconsin Alumni Research Foundation Fluorescence assays with improved blocking groups
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
KR20060120141A (ko) * 2003-11-24 2006-11-24 네오스 테크놀로지스, 인크. 글리코페질화 에리트로포이에틴
BRPI0417342A (pt) * 2003-12-03 2007-04-17 Neose Technologies Inc fator estimulante de colÈnia de granulócitos glicopeguilado
US7956032B2 (en) 2003-12-03 2011-06-07 Novo Nordisk A/S Glycopegylated granulocyte colony stimulating factor
KR101439880B1 (ko) * 2004-01-08 2014-09-12 라티오팜 게엠베하 펩티드의 오-결합형 글리코실화
EP1771066A2 (en) 2004-07-13 2007-04-11 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
EP1799249A2 (en) * 2004-09-10 2007-06-27 Neose Technologies, Inc. Glycopegylated interferon alpha
AU2005289404A1 (en) * 2004-09-28 2006-04-06 Baylor University Spatially-defined modification of fresh tissue using covalent chemistry
EP1812864A2 (en) * 2004-10-07 2007-08-01 Emory University Multifunctional nanoparticles conjugates and their use
WO2006050247A2 (en) * 2004-10-29 2006-05-11 Neose Technologies, Inc. Remodeling and glycopegylation of fibroblast growth factor (fgf)
US20060216760A1 (en) * 2004-12-22 2006-09-28 California Institute Of Technology Methods for proteomic profiling using non-natural amino acids
EP1838332A1 (en) * 2005-01-06 2007-10-03 Neose Technologies, Inc. Glycoconjugation using saccharyl fragments
NZ556436A (en) * 2005-01-10 2010-11-26 Biogenerix Ag 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
GB0507123D0 (en) * 2005-04-08 2005-05-11 Isis Innovation Method
EP2386571B1 (en) 2005-04-08 2016-06-01 ratiopharm GmbH Compositions and methods for the preparation of protease resistant human growth hormone glycosylation mutants
WO2006127910A2 (en) * 2005-05-25 2006-11-30 Neose Technologies, Inc. Glycopegylated erythropoietin formulations
US20110003744A1 (en) * 2005-05-25 2011-01-06 Novo Nordisk A/S 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
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
EP3591069A3 (en) * 2005-10-27 2020-03-04 The President and Fellows of Harvard College Methods and compositions for labeling nucleic acids
US20090048440A1 (en) 2005-11-03 2009-02-19 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
CN101389675B (zh) * 2006-02-21 2012-06-20 亨茨曼国际有限公司 制备聚异氰脲酸酯复合材料的方法
US8816050B2 (en) * 2006-03-22 2014-08-26 The Scripps Research Institute Method of preparing glycopeptides
ES2516694T3 (es) * 2006-07-21 2014-10-31 Ratiopharm Gmbh Glicosilación de péptidos a través de secuencias de glicosilación con unión en O
US7985783B2 (en) 2006-09-21 2011-07-26 The Regents Of The University Of California Aldehyde tags, uses thereof in site-specific protein modification
WO2008057683A2 (en) 2006-10-03 2008-05-15 Novo Nordisk A/S Methods for the purification of polypeptide conjugates
LT2068907T (lt) * 2006-10-04 2018-01-10 Novo Nordisk A/S Glicerolio sujungti pegilinti sacharidai ir glikopeptidai
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.
US20110177029A1 (en) * 2007-06-04 2011-07-21 Novo Nordisk A/S O-linked glycosylation using n-acetylglucosaminyl transferases
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
US20100286067A1 (en) * 2008-01-08 2010-11-11 Biogenerix Ag Glycoconjugation of polypeptides using oligosaccharyltransferases
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US8034396B2 (en) * 2008-04-01 2011-10-11 Tyco Healthcare Group Lp Bioadhesive composition formed using click chemistry
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WO2010057220A1 (en) 2008-11-17 2010-05-20 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
EP2398523B1 (en) 2009-02-21 2018-04-04 Covidien LP Medical devices having activated surfaces
WO2010096654A1 (en) 2009-02-21 2010-08-26 Tyco Healthcare Group Lp Medical devices having activated surfaces
AU2010215199B2 (en) 2009-02-21 2015-01-15 Sofradim Production Compounds and medical devices activated with solvophobic linkers
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US8663689B2 (en) * 2009-02-21 2014-03-04 Sofradim Production Functionalized adhesive medical gel
US9375699B2 (en) 2009-02-21 2016-06-28 Sofradim Production Apparatus and method of reacting polymers by exposure to UV radiation to produce injectable medical devices
AU2010215192B2 (en) 2009-02-21 2015-04-30 Sofradim Production Amphiphilic compounds and self-assembling compositions made therefrom
AU2010215202A1 (en) 2009-02-21 2011-10-13 Covidien Lp Crosslinked fibers and method of making same using UV radiation
US8968733B2 (en) * 2009-02-21 2015-03-03 Sofradim Production Functionalized surgical adhesives
WO2010095056A2 (en) 2009-02-21 2010-08-26 Sofradim Production Medical devices with an activated coating
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
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
CA2805987C (en) 2010-07-27 2019-04-09 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
EP2966061B1 (en) 2011-03-04 2017-05-03 Life Technologies Corporation Compounds and methods for conjugation of biomolecules
US9145361B2 (en) 2011-03-25 2015-09-29 Life Technologies Corporation SDP-containing heterobifunctional agents
US9556195B2 (en) 2011-09-12 2017-01-31 The Regents Of The University Of California Compositions and methods for quadricyclane modification of biomolecules
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
US9493413B2 (en) 2013-11-27 2016-11-15 Redwood Bioscience, Inc. Hydrazinyl-pyrrolo compounds and methods for producing a conjugate
US20180215783A1 (en) * 2015-08-13 2018-08-02 The Regents Of The University Of California Bioorthogonal reaction of an amine n-oxide and a boron agent
US10195283B2 (en) 2016-03-18 2019-02-05 R.P. Scherer Technologies, Llc Hydrazinyl-substituted heteroaryl compounds and methods for producing a conjugate
AU2017257504A1 (en) 2016-04-26 2018-10-25 R.P. Scherer Technologies, Llc Antibody conjugates and methods of making and using the same
US20190177438A1 (en) 2016-06-17 2019-06-13 Life Technologies Corporation Site-Specific Crosslinking of Antibodies
US10814036B2 (en) 2016-11-07 2020-10-27 Baylor University Drug-eluting live tissue for transplantation
US11890319B2 (en) 2017-01-18 2024-02-06 Visterra, Inc. Antibody molecule-drug conjugates and uses thereof
MX2021003760A (es) 2019-04-29 2021-09-21 Illumina Inc Identificacion y analisis de muestras microbianas por incubacion rapida y enriquecimiento de acido nucleico.
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EP4108669A1 (en) * 2021-06-24 2022-12-28 Institute Of Organic Chemistry And Biochemistry As CR, V.V.I. Carbohydrate derivatives and kits for cell surface labeling
US11879010B2 (en) 2021-09-30 2024-01-23 The Charlotte Mecklenburg Hospital Authority Methods and compositions for pretargeted immunotherapy
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

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989008657A2 (fr) * 1988-03-09 1989-09-21 Cis Bio Internatonal Preparation de complexes nitruro utilisables comme produits radiopharmaceutiques

Family Cites Families (6)

* 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
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
EP1263771B1 (en) 2000-03-16 2006-06-14 The Regents Of The University Of California Chemoselective ligation by use of a phosphine
JP4694085B2 (ja) 2000-05-12 2011-06-01 ウィスコンシン アルムニ リサーチ ファンデイション アミド結合を形成するためのライゲーション方法及び試薬

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989008657A2 (fr) * 1988-03-09 1989-09-21 Cis Bio Internatonal Preparation de complexes nitruro utilisables comme produits radiopharmaceutiques

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
G M[RKL & G YU JIN: "1,5-Diaza-3-phospha-cycloheptane-N,N'-Bis -ÄphosphinomethylÜ-ethylendiamine mit optisch aktiven Seitenketten" TETRAHEDRON LETTERS., vol. 21, 1980, pages 3467-3470, XP002188900 ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL ISSN: 0040-4039 *
J CHATT ET AL.: "Rhodium(I), rhodium(II), palladium(II) and platinum(II) complexes containing ligands of the type PRnQ3-n (n=0, 1 or 2; R=Mem Et, But or Ph; Q=CH2OCOMe or CH2OH) " JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS., no. 19, 1973, pages 2021-2028, XP002188899 CHEMICAL SOCIETY. LETCHWORTH., GB ISSN: 1472-7773 *
O HERD ET AL: "Water-soluble phosphines VIII. Palladium-catalyzed P-C cross coupling reactions between primary or secondary phosphines and functional aryliodides - a novel synthetic route to water-soluble phosphines" JOURNAL OF ORGANOMETALLIC CHEMISTRY., vol. 522, 1996, pages 69-76, XP002188898 ELSEVIER-SEQUOIA S.A. LAUSANNE., CH ISSN: 0022-328X *
SAXON, ELIANA (1) ET AL: "Development of a new chemoselective ligation reaction." ABSTRACTS OF PAPERS AMERICAN CHEMICAL SOCIETY, (1999) VOL. 218, NO. 1-2, PP. CARB 23. MEETING INFO.: 218TH NATIONAL MEETING OF THE AMERICAN CHEMICAL SOCIETY, PARTS 1 AND 2 NEW ORLEANS, LOUISIANA, USA AUGUST 22-26, 1999 AMERICAN CHEMICAL SOCIETY. , XP001059669 *
SAXON, ELIANA ET AL: "Cell surface engineering by a modified Staudinger reaction." SCIENCE (WASHINGTON D C), (MARCH 17, 2000) VOL. 287, NO. 5460, PP. 2007-2010. PRINT. , XP002188901 *
See also references of EP1263771A2 *

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* Cited by examiner, † Cited by third party
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US20060276658A1 (en) 2006-12-07
US20070037964A1 (en) 2007-02-15
US7939626B2 (en) 2011-05-10
US6570040B2 (en) 2003-05-27
EP1263771A2 (en) 2002-12-11
DE60120650T2 (de) 2007-05-31
EP1263771B1 (en) 2006-06-14
US20020016003A1 (en) 2002-02-07
US7838665B2 (en) 2010-11-23
WO2001068565A3 (en) 2002-05-23
US20030199084A1 (en) 2003-10-23
DE60120650D1 (de) 2006-07-27
US7923582B2 (en) 2011-04-12
ATE329925T1 (de) 2006-07-15
US20110236930A1 (en) 2011-09-29
US20050148032A1 (en) 2005-07-07
US7667012B2 (en) 2010-02-23
US8076496B2 (en) 2011-12-13
US20080214801A1 (en) 2008-09-04
US7122703B2 (en) 2006-10-17

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