AU2015271886B2 - Improved coupling method for peptide synthesis at elevated temperatures - Google Patents

Improved coupling method for peptide synthesis at elevated temperatures Download PDF

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Publication number
AU2015271886B2
AU2015271886B2 AU2015271886A AU2015271886A AU2015271886B2 AU 2015271886 B2 AU2015271886 B2 AU 2015271886B2 AU 2015271886 A AU2015271886 A AU 2015271886A AU 2015271886 A AU2015271886 A AU 2015271886A AU 2015271886 B2 AU2015271886 B2 AU 2015271886B2
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Australia
Prior art keywords
coupling
base
activation
diea
amino acid
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AU2015271886A
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AU2015271886A1 (en
Inventor
Jonathan M. Collins
Sandeep Kumar Singh
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CEM Corp
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CEM Corp
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Priority to AU2017204172A priority Critical patent/AU2017204172B2/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
    • C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling 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
    • C07K1/06—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
    • 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
    • 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
    • C07K1/084—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 nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/57581—Thymosin; Related peptides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Biophysics (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Endocrinology (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Peptides Or Proteins (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
AU2015271886A 2014-12-19 2015-12-17 Improved coupling method for peptide synthesis at elevated temperatures Active AU2015271886B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2017204172A AU2017204172B2 (en) 2014-12-19 2017-06-20 Improved coupling method for peptide synthesis at elevated temperatures

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US201462094420P 2014-12-19 2014-12-19
US62/094,420 2014-12-19
US201562111817P 2015-02-04 2015-02-04
US62/111,817 2015-02-04
US201562132847P 2015-03-13 2015-03-13
US62/132,847 2015-03-13
US14/969,004 2015-12-15
US14/969,004 US10308677B2 (en) 2014-12-19 2015-12-15 Coupling method for peptide synthesis at elevated temperatures

Related Child Applications (1)

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AU2017204172A Division AU2017204172B2 (en) 2014-12-19 2017-06-20 Improved coupling method for peptide synthesis at elevated temperatures

Publications (2)

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AU2015271886A1 AU2015271886A1 (en) 2016-07-07
AU2015271886B2 true AU2015271886B2 (en) 2017-08-03

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AU2015271886A Active AU2015271886B2 (en) 2014-12-19 2015-12-17 Improved coupling method for peptide synthesis at elevated temperatures
AU2017204172A Active AU2017204172B2 (en) 2014-12-19 2017-06-20 Improved coupling method for peptide synthesis at elevated temperatures

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AU2017204172A Active AU2017204172B2 (en) 2014-12-19 2017-06-20 Improved coupling method for peptide synthesis at elevated temperatures

Country Status (6)

Country Link
US (1) US10308677B2 (enExample)
EP (1) EP3037430B1 (enExample)
JP (1) JP6348102B2 (enExample)
CN (1) CN105713066A (enExample)
AU (2) AU2015271886B2 (enExample)
CA (1) CA2915484C (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUE034308T2 (en) 2013-03-21 2018-02-28 Sanofi Aventis Deutschland Preparation of hydantoin-containing peptide products
US10450343B2 (en) 2013-03-21 2019-10-22 Sanofi-Aventis Deutschland Gmbh Synthesis of cyclic imide containing peptide products
US9969769B2 (en) 2014-12-19 2018-05-15 Cem Corporation Coupling method for peptide synthesis at elevated temperatures
AU2017221772B2 (en) * 2016-09-02 2018-07-05 Cem Corporation Use of excess carbodiimide for peptide synthesis at elevated temperatures
US10858390B2 (en) 2016-09-02 2020-12-08 Cem Corporation Use of excess carbodiimide for peptide synthesis at elevated temperatures
CN113655133B (zh) * 2021-06-29 2023-03-10 北京诺康达医药科技股份有限公司 一种检测n,n-二异丙基碳二酰亚胺的方法及应用
CN114736286B (zh) * 2021-12-27 2024-09-13 江苏诺泰澳赛诺生物制药股份有限公司 一种多肽杂质单硫化物的合成方法
EP4488283A1 (en) * 2022-04-08 2025-01-08 Chugai Seiyaku Kabushiki Kaisha Production method for peptide compound
CN118812623A (zh) * 2024-07-02 2024-10-22 中肽生化有限公司 一种alpha取代氨基酸和氮烷基类甘氨酸相连多肽序列的固相合成方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005063791A2 (en) * 2003-12-31 2005-07-14 F. Hoffmann-La Roche Ag Process for peptide synthesis using a reduced amount of deprotection agent

Family Cites Families (14)

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Publication number Priority date Publication date Assignee Title
GB673639A (en) 1948-07-02 1952-06-11 Ward Blenkinsop & Co Ltd Process for the production of acyl derivatives of amino hydroxybenzene carboxylic acids
GB812543A (en) 1954-12-06 1959-04-29 Roussel Uclaf Improvements in or relating to ª‡-amino acids and peptides derived therefrom
US4507230A (en) 1982-05-12 1985-03-26 Research Corporation Peptide synthesis reagents and method of use
JPS6393796A (ja) 1986-10-09 1988-04-25 Shin Etsu Chem Co Ltd ペプチド合成の脱保護基用薬剤
DE3887670D1 (de) 1987-12-22 1994-03-17 Hoechst Ag Säurelabile Ankergruppen zur Synthese von Peptidamiden mittels Festphasenmethode.
DE4124283A1 (de) 1991-07-15 1993-01-21 Degussa Umesterung von peptiden
BR9811594A (pt) 1997-07-31 2000-09-05 Elan Pharm Inc Compostos de dipeptìdeo sulfonilados que inibem adesão de leucócito mediada por vla-4
ATE264870T1 (de) 2000-01-27 2004-05-15 Lilly Co Eli Verfahren zur lösung von glucagon-ähnlichen peptid-1 (glp-1) verbindungen
ES2266104T3 (es) 2000-12-22 2007-03-01 Ipsen Manufacturing Ireland Limited Procedimiento para la sintesis de un peptido lhrh.
GB0227876D0 (en) 2002-11-29 2003-01-08 Avecia Ltd Process and supports
US7393920B2 (en) * 2003-06-23 2008-07-01 Cem Corporation Microwave-assisted peptide synthesis
DE102004053410A1 (de) 2004-11-05 2006-05-11 Bayer Healthcare Ag Cyclische Nonadepsipeptidamide
JP6112011B2 (ja) 2011-05-31 2017-04-12 味の素株式会社 ペプチドの製造方法
US20140206841A1 (en) 2013-01-18 2014-07-24 Protein Technologies, Inc. Peptide Synthesis Apparatus and Methods Using Infrared Energy

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005063791A2 (en) * 2003-12-31 2005-07-14 F. Hoffmann-La Roche Ag Process for peptide synthesis using a reduced amount of deprotection agent

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BACSA et al. "Solid-Phase Synthesis of Difficult Peptide Sequences at Elevated Temperatures: A Critical Comparison of Microwave and Conventional Heating Technologies", Journal of Organic Chemistry, 2008, Vol. 73, Pages 7532-7542. *
BEYERMANN et al. "Effect of tertiary amine on the carbodiimide-mediated peptide synthesis", International Journal of Peptide and Protein Research, 1991, Vol. 37, Pages 252-256. *
CARPINO et al. "The Diisopropylcarbodiimide/1-Hydroxy-7-azabenzotriazole System: Segment Coupling and Stepwise Peptide Assembly", Tetrahedron, 1999, Vol. 55, Pages 6813-6830. *
COLLINS et al. "High Efficiency Solid Phase Peptide Synthesis (HE-SPPS) – Supporting Information", Organic Letters, Jan 2014, Pages S1-S11, Document ol4036825_si_001.pdf retrieved online at http://pubs.acs.org/doi/suppl/10.1021/ol4036825. *
COLLINS et al. "High-efficiency Solid Phase Peptide Synthesis (HE-SPPS)", Organic Letters, Jan 2014, Vol. 16, No. 3, Pages 940-943. *

Also Published As

Publication number Publication date
CA2915484A1 (en) 2016-06-19
EP3037430A1 (en) 2016-06-29
JP6348102B2 (ja) 2018-06-27
CN105713066A (zh) 2016-06-29
EP3037430B1 (en) 2019-12-04
AU2017204172B2 (en) 2017-10-05
CA2915484C (en) 2019-01-15
JP2016138090A (ja) 2016-08-04
AU2015271886A1 (en) 2016-07-07
US20160176918A1 (en) 2016-06-23
AU2017204172A1 (en) 2017-07-13
US10308677B2 (en) 2019-06-04

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