AU745094B2 - Solid phase native chemical ligation of unprotected or N-terminal cysteine protected peptides in aqueous solution - Google Patents
Solid phase native chemical ligation of unprotected or N-terminal cysteine protected peptides in aqueous solution Download PDFInfo
- Publication number
- AU745094B2 AU745094B2 AU80695/98A AU8069598A AU745094B2 AU 745094 B2 AU745094 B2 AU 745094B2 AU 80695/98 A AU80695/98 A AU 80695/98A AU 8069598 A AU8069598 A AU 8069598A AU 745094 B2 AU745094 B2 AU 745094B2
- Authority
- AU
- Australia
- Prior art keywords
- peptide
- solid phase
- terminal
- bound
- unprotected
- 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.)
- Ceased
Links
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- 108091005601 modified peptides Proteins 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- HIGSLXSBYYMVKI-UHFFFAOYSA-N pralidoxime chloride Chemical compound [Cl-].C[N+]1=CC=CC=C1\C=N\O HIGSLXSBYYMVKI-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
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
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/08—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents
- C07K1/086—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents containing sulfur
-
- 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
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
- C07K1/026—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution by fragment condensation in solution
-
- 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
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/047—Simultaneous synthesis of different peptide species; Peptide libraries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4955397P | 1997-06-13 | 1997-06-13 | |
| US60/049553 | 1997-06-13 | ||
| PCT/US1998/012278 WO1998056807A1 (en) | 1997-06-13 | 1998-06-12 | Solid phase native chemical ligation of unprotected or n-terminal cysteine protected peptides in aqueous solution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8069598A AU8069598A (en) | 1998-12-30 |
| AU745094B2 true AU745094B2 (en) | 2002-03-14 |
Family
ID=21960431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU80695/98A Ceased AU745094B2 (en) | 1997-06-13 | 1998-06-12 | Solid phase native chemical ligation of unprotected or N-terminal cysteine protected peptides in aqueous solution |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US6326468B1 (https=) |
| EP (1) | EP1001968B1 (https=) |
| JP (1) | JP2002505672A (https=) |
| AT (2) | ATE285415T1 (https=) |
| AU (1) | AU745094B2 (https=) |
| CA (1) | CA2292724A1 (https=) |
| DE (2) | DE69828287T2 (https=) |
| ES (2) | ES2282788T3 (https=) |
| WO (1) | WO1998056807A1 (https=) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6184344B1 (en) * | 1995-05-04 | 2001-02-06 | The Scripps Research Institute | Synthesis of proteins by native chemical ligation |
| US6849428B1 (en) * | 1997-03-05 | 2005-02-01 | New England Biolabs, Inc. | Intein-mediated protein ligation of expressed proteins |
| ATE285415T1 (de) * | 1997-06-13 | 2005-01-15 | Gryphon Therapeutics Inc | Festphasige native chemische ligation von ungeschützten oder n-cystein-geschützten peptiden in wässrigen lösungen |
| EP1009757A1 (en) | 1997-09-04 | 2000-06-21 | Gryphon Sciences | Modular protein libraries and methods of preparation |
| AUPP589598A0 (en) | 1998-09-14 | 1998-10-08 | University Of Queensland, The | Novel peptides |
| US7001745B1 (en) * | 1998-09-30 | 2006-02-21 | New England Biolabs, Inc. | Intein mediated peptide ligation |
| CN1350544A (zh) * | 1999-03-11 | 2002-05-22 | 格莱风科学公司 | 可溶性膜蛋白受体结构域的化学合成及应用 |
| SK782002A3 (en) | 1999-07-21 | 2003-08-05 | Lexigen Pharm Corp | FC fusion proteins for enhancing the immunogenicity of protein and peptide antigens |
| US20040014082A1 (en) * | 2000-08-11 | 2004-01-22 | Invitrogen Corporation | Highly homogeneous molecular markers for electrophoresis |
| JP2004506221A (ja) * | 2000-08-11 | 2004-02-26 | インヴィトロジェン コーポレーション | 高度に均一な電気泳動用分子マーカー |
| KR20030046389A (ko) * | 2000-09-01 | 2003-06-12 | 그리폰 테라퓨틱스, 인코포레이티드 | 친핵체에 안정한 티오에스테르 발생 화합물, 제조 및 사용방법 |
| WO2002057294A2 (en) * | 2001-01-22 | 2002-07-25 | Sangamo Biosciences, Inc. | Zinc finger proteins for dna binding and gene regulation in plants |
| EP1412517B1 (en) * | 2001-03-09 | 2006-11-29 | Boston Probes, Inc. | Methods, kits and compositions of combination oligomers |
| GB0113657D0 (en) * | 2001-06-05 | 2001-07-25 | Geneprot Inc | Improved native chemical ligation with three or more components |
| EP2042196B1 (en) | 2001-10-10 | 2016-07-13 | ratiopharm GmbH | Remodelling and glycoconjugation of Granulocyte Colony Stimulating Factor (G-CSF) |
| ES2340376T3 (es) * | 2002-06-10 | 2010-06-02 | Amylin Pharmaceuticals, Inc. | Desproteccion del azufre posterior a la escision para la sintesis convergente de proteinas mediante ligacion quimica. |
| JP2005531616A (ja) * | 2002-06-29 | 2005-10-20 | アクヴァノヴァ・ジャーマン・ソリュービリセイト・テクノロジーズ・（アーゲーテー）・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | イソフラボン濃縮物およびその製造法 |
| US7598224B2 (en) | 2002-08-20 | 2009-10-06 | Biosurface Engineering Technologies, Inc. | Dual chain synthetic heparin-binding growth factor analogs |
| US8227411B2 (en) | 2002-08-20 | 2012-07-24 | BioSurface Engineering Technologies, Incle | FGF growth factor analogs |
| US7166574B2 (en) * | 2002-08-20 | 2007-01-23 | Biosurface Engineering Technologies, Inc. | Synthetic heparin-binding growth factor analogs |
| WO2004053460A2 (en) * | 2002-12-11 | 2004-06-24 | New England Biolabs, Inc. | Carrier-ligand fusions and uses thereof |
| US8034900B2 (en) | 2002-12-30 | 2011-10-11 | Amylin Pharmaceuticals, Inc. | Water-soluble thioester and selenoester compounds and methods for making and using the same |
| EP2055189A1 (en) | 2003-04-09 | 2009-05-06 | Neose Technologies, Inc. | Glycopegylation methods and proteins/peptides produced by the methods |
| PT1624891E (pt) | 2003-05-06 | 2010-01-05 | Syntonix Pharmaceuticals Inc | Proteínas quiméricas de factor de coagulação-fc destinadas ao tratamento da hemofilia |
| US7348004B2 (en) | 2003-05-06 | 2008-03-25 | Syntonix Pharmaceuticals, Inc. | Immunoglobulin chimeric monomer-dimer hybrids |
| TWI353991B (en) * | 2003-05-06 | 2011-12-11 | Syntonix Pharmaceuticals Inc | Immunoglobulin chimeric monomer-dimer hybrids |
| WO2004105685A2 (en) * | 2003-05-22 | 2004-12-09 | Gryphon Therapeutics, Inc. | Displaceable linker solid phase chemical ligation |
| US7414028B1 (en) | 2004-02-04 | 2008-08-19 | Biosurface Engineering Technologies, Inc. | Growth factor analogs |
| US7528105B1 (en) | 2004-02-10 | 2009-05-05 | Biosurface Engineering Technologies | Heterodimeric chain synthetic heparin-binding growth factor analogs |
| US7671012B2 (en) | 2004-02-10 | 2010-03-02 | Biosurface Engineering Technologies, Inc. | Formulations and methods for delivery of growth factor analogs |
| US20080227696A1 (en) | 2005-02-22 | 2008-09-18 | Biosurface Engineering Technologies, Inc. | Single branch heparin-binding growth factor analogs |
| US20060024347A1 (en) * | 2004-02-10 | 2006-02-02 | Biosurface Engineering Technologies, Inc. | Bioactive peptide coatings |
| ATE482228T1 (de) | 2004-02-20 | 2010-10-15 | Biosurface Eng Tech Inc | Positiver modulator des knochenmorphogenetisches protein-2 (bmp-2) |
| RU2413731C2 (ru) | 2004-04-09 | 2011-03-10 | Чугаи Сейяку Кабусики Кайся | Новые растворимые в воде пролекарства |
| WO2005115433A2 (en) * | 2004-05-24 | 2005-12-08 | Rigel Pharmaceuticals, Inc. | Methods for cyclizing synthetic polymers |
| EP2258382A3 (en) | 2005-03-31 | 2014-05-14 | Amylin Pharmaceuticals, LLC | Amylin and amylin agonists for treating psychiatric diseases and disorders |
| TW200744603A (en) | 2005-08-22 | 2007-12-16 | Chugai Pharmaceutical Co Ltd | Novel anticancer concomitant drug |
| US7674881B2 (en) * | 2005-10-07 | 2010-03-09 | The University Of Chicago | Convergent synthesis of proteins by kinetically controlled ligation |
| CA2626330A1 (en) * | 2005-10-19 | 2007-04-26 | Chugai Seiyaku Kabushiki Kaisha | Preventive or therapeutic agents for pancreatic cancer, ovarian cancer, or liver cancer comprising a novel water-solube prodrug |
| US7820172B1 (en) | 2006-06-01 | 2010-10-26 | Biosurface Engineering Technologies, Inc. | Laminin-derived multi-domain peptides |
| JP2009541358A (ja) | 2006-06-22 | 2009-11-26 | バイオサーフェス エンジニアリング テクノロジーズ，インク． | 骨形成を強化するためにｂｍｐ−２増幅因子／共活性化因子を送達するための組成物および方法 |
| EP2120985B1 (en) | 2007-02-05 | 2012-06-27 | Amylin Pharmaceuticals, Inc. | FN-38 peptides for use in the treatment of psychotic and anxiety disorders |
| JP2010537984A (ja) * | 2007-08-28 | 2010-12-09 | イプセン ファルマ ソシエテ パール アクシオン サンプリフィエ | ポリペプチドおよび蛋白質の化学合成のための方法および中間体 |
| WO2011103409A1 (en) * | 2010-02-18 | 2011-08-25 | Advanced Proteome Therapeutics Inc. | Site-specific modification of proteins through chemical modification enabling protein conjugates, protein dimer formation, and stapled peptides |
| WO2012050923A2 (en) | 2010-09-28 | 2012-04-19 | Amylin Pharmaceuticals, Inc. | Engineered polypeptides having enhanced duration of action |
| ES2630031T3 (es) | 2010-09-28 | 2017-08-17 | Aegerion Pharmaceuticals, Inc. | Un polipéptido de leptina pinnípedo-humano quimérico con solubilidad aumentada |
| ES2732475T3 (es) | 2011-07-08 | 2019-11-22 | Aegerion Pharmaceuticals Inc | Polipéptidos modificados por ingeniería genética que tienen una duración potenciada de la acción y una inmunogenicidad reducida |
| JP6006309B2 (ja) | 2011-07-08 | 2016-10-12 | アミリン・ファーマシューティカルズ, リミテッド・ライアビリティ・カンパニーAmylin Pharmaceuticals, Llc | 作用持続期間が増大し、免疫原性が減少した操作されたポリペプチド |
| FR2981352B1 (fr) * | 2011-10-17 | 2015-07-03 | Centre Nat Rech Scient | Procede de synthese de proteines |
| CA2873112A1 (en) | 2012-05-11 | 2013-11-14 | Alexander Krantz | Site-specific labeling and targeted delivery of proteins for the treatment of cancer |
| US9731029B2 (en) | 2012-05-21 | 2017-08-15 | Massachusetts Institute Of Technology | Protein retrosplicing enabled by a double ligation reaction |
| AR095527A1 (es) | 2013-03-15 | 2015-10-21 | Biogen Idec Inc | Formulaciones de polipéptido fc-factor ix |
| US11273176B2 (en) | 2016-03-02 | 2022-03-15 | The Brigham And Women's Hospital, Inc. | Use of PLA2G5-deficient suppressive macrophages in suppression of inflammation |
| KR102544146B1 (ko) | 2017-03-02 | 2023-06-15 | 가부시키가이샤 도우사 고가쿠 겐큐쇼 | 아미노산 중합체의 제조방법 |
| CN113166196A (zh) | 2018-10-01 | 2021-07-23 | 日内瓦大学 | 用于生成适合生物学分析的多种多肽变体的方法 |
| JP7281826B2 (ja) * | 2018-11-30 | 2023-05-26 | 株式会社糖鎖工学研究所 | ペプチドチオエステル、ペプチドの新規製造方法 |
| AU2020361681A1 (en) | 2019-10-10 | 2022-05-05 | 1859, Inc. | Methods and systems for microfluidic screening |
| CN110945009B (zh) * | 2019-10-23 | 2023-10-31 | 烟台迈百瑞国际生物医药股份有限公司 | 一种寡肽连接子中间体及其制备方法 |
| WO2022266467A2 (en) | 2021-06-17 | 2022-12-22 | Dana-Farber Cancer Institute, Inc. | Recombinant histone polypeptide and uses thereof |
| EP4646232A1 (en) | 2023-01-06 | 2025-11-12 | Université de Genève | Variant ligand conjugates for payload delivery |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5064940A (en) * | 1988-05-11 | 1991-11-12 | Protein Technologies, Inc. | Premixed dry reagent containing a protected amino acid and an activating agent for use in solid phase protein synthesis |
| US5101059A (en) * | 1989-12-05 | 1992-03-31 | Research Corporation Technologies, Inc. | Amino acid protecting groups |
| SI0832096T1 (en) * | 1995-05-04 | 2001-12-31 | Scripps Research Inst | Synthesis of proteins by native chemical ligation |
| WO1998028434A1 (en) * | 1996-12-24 | 1998-07-02 | The Scripps Research Institute | General chemical ligation |
| ATE285415T1 (de) * | 1997-06-13 | 2005-01-15 | Gryphon Therapeutics Inc | Festphasige native chemische ligation von ungeschützten oder n-cystein-geschützten peptiden in wässrigen lösungen |
| US6329468B1 (en) * | 2000-01-21 | 2001-12-11 | Bostik Findley, Inc. | Hot melt adhesive based on semicrystalline flexible polyolefins |
-
1998
- 1998-06-12 AT AT98929035T patent/ATE285415T1/de not_active IP Right Cessation
- 1998-06-12 CA CA002292724A patent/CA2292724A1/en not_active Abandoned
- 1998-06-12 US US09/097,094 patent/US6326468B1/en not_active Expired - Fee Related
- 1998-06-12 ES ES04029270T patent/ES2282788T3/es not_active Expired - Lifetime
- 1998-06-12 ES ES98929035T patent/ES2235336T3/es not_active Expired - Lifetime
- 1998-06-12 DE DE69828287T patent/DE69828287T2/de not_active Expired - Fee Related
- 1998-06-12 AT AT04029270T patent/ATE354584T1/de not_active IP Right Cessation
- 1998-06-12 WO PCT/US1998/012278 patent/WO1998056807A1/en not_active Ceased
- 1998-06-12 EP EP98929035A patent/EP1001968B1/en not_active Expired - Lifetime
- 1998-06-12 DE DE69837170T patent/DE69837170T2/de not_active Expired - Fee Related
- 1998-06-12 AU AU80695/98A patent/AU745094B2/en not_active Ceased
- 1998-06-12 JP JP50326799A patent/JP2002505672A/ja not_active Ceased
-
2001
- 2001-11-15 US US09/987,655 patent/US7094871B2/en not_active Expired - Fee Related
- 2001-11-15 US US09/987,675 patent/US7030217B2/en not_active Expired - Fee Related
-
2005
- 2005-05-03 US US11/119,831 patent/US20050209440A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20020132975A1 (en) | 2002-09-19 |
| JP2002505672A (ja) | 2002-02-19 |
| DE69828287D1 (de) | 2005-01-27 |
| ES2235336T3 (es) | 2005-07-01 |
| AU8069598A (en) | 1998-12-30 |
| US7094871B2 (en) | 2006-08-22 |
| DE69828287T2 (de) | 2005-12-15 |
| DE69837170T2 (de) | 2007-11-22 |
| US7030217B2 (en) | 2006-04-18 |
| US20050209440A1 (en) | 2005-09-22 |
| EP1001968A1 (en) | 2000-05-24 |
| ATE354584T1 (de) | 2007-03-15 |
| WO1998056807A1 (en) | 1998-12-17 |
| US6326468B1 (en) | 2001-12-04 |
| DE69837170D1 (de) | 2007-04-05 |
| EP1001968B1 (en) | 2004-12-22 |
| ES2282788T3 (es) | 2007-10-16 |
| CA2292724A1 (en) | 1998-12-17 |
| ATE285415T1 (de) | 2005-01-15 |
| US20020169282A1 (en) | 2002-11-14 |
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Legal Events
| Date | Code | Title | Description |
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| FGA | Letters patent sealed or granted (standard patent) |