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 US10308677B2 (en) 2014-12-19 2015-12-15 Coupling method for peptide synthesis at elevated temperatures
US14/969,004 2015-12-15

Related Child Applications (1)

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

Publications (2)

Publication Number Publication Date
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
WO2014147124A1 (en) 2013-03-21 2014-09-25 Sanofi-Aventis Deutschland Gmbh Synthesis of hydantoin containing peptide products
MX365465B (es) 2013-03-21 2019-06-04 Sanofi Aventis Deutschland Sintesis de productos peptidicos que contienen imida ciclica.
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
KR20240169679A (ko) * 2022-04-08 2024-12-03 추가이 세이야쿠 가부시키가이샤 펩타이드 화합물의 제조 방법
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
ES2061714T3 (es) 1987-12-22 1994-12-16 Hoechst Ag Grupos de anclaje inestables frente a acidos para la sintesis de amidas peptidicas mediante el metodo en fase solida.
DE4124283A1 (de) 1991-07-15 1993-01-21 Degussa Umesterung von peptiden
WO1999006437A1 (en) 1997-07-31 1999-02-11 Elan Pharmaceuticals Inc. Sulfonylated dipeptide compounds which inhibit leukocyte adhesion mediated by vla-4
TR200401142T4 (tr) 2000-01-27 2004-07-21 Eli Lilly And Company Glükagon-benzeri peptid bileşiklerinin çözündürülmesi için işlem.
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
WO2012165546A1 (ja) 2011-05-31 2012-12-06 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
AU2017204172A1 (en) 2017-07-13
CA2915484C (en) 2019-01-15
EP3037430B1 (en) 2019-12-04
CN105713066A (zh) 2016-06-29
AU2017204172B2 (en) 2017-10-05
JP2016138090A (ja) 2016-08-04
CA2915484A1 (en) 2016-06-19
JP6348102B2 (ja) 2018-06-27
US20160176918A1 (en) 2016-06-23
US10308677B2 (en) 2019-06-04
AU2015271886A1 (en) 2016-07-07
EP3037430A1 (en) 2016-06-29

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