WO2004007661A3 - Carboxy protection strategies for acidic c-terminal amino acids in chemical ligation of oligopeptides - Google Patents
Carboxy protection strategies for acidic c-terminal amino acids in chemical ligation of oligopeptides Download PDFInfo
- Publication number
- WO2004007661A3 WO2004007661A3 PCT/IB2003/005473 IB0305473W WO2004007661A3 WO 2004007661 A3 WO2004007661 A3 WO 2004007661A3 IB 0305473 W IB0305473 W IB 0305473W WO 2004007661 A3 WO2004007661 A3 WO 2004007661A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oligopeptides
- acidic
- chemical ligation
- amino acids
- present
- Prior art date
Links
- 108010038807 Oligopeptides Proteins 0.000 title abstract 6
- 102000015636 Oligopeptides Human genes 0.000 title abstract 6
- 230000002378 acidificating effect Effects 0.000 title abstract 3
- 239000000126 substance Substances 0.000 title abstract 3
- 125000001433 C-terminal amino-acid group Chemical group 0.000 title 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title 1
- 229920001184 polypeptide Polymers 0.000 abstract 3
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 3
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 3
- 210000004899 c-terminal region Anatomy 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 102000004169 proteins and genes Human genes 0.000 abstract 2
- 108090000623 proteins and genes Proteins 0.000 abstract 2
- 150000007970 thio esters Chemical class 0.000 abstract 2
- 102000007079 Peptide Fragments Human genes 0.000 abstract 1
- 108010033276 Peptide Fragments Proteins 0.000 abstract 1
- -1 aspartyl Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 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
- C07K1/04—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
- C07K1/061—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 protecting groups
-
- 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
- C07K1/061—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 protecting groups
- C07K1/062—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 protecting groups for alpha- or omega-carboxy functions
-
- 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
- C07K1/061—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 protecting groups
- C07K1/065—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 protecting groups for hydroxy functions, not being part of carboxy functions
-
- 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
- C07K1/061—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 protecting groups
- C07K1/067—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 protecting groups for sulfur-containing functions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004521045A JP4327718B2 (en) | 2002-06-10 | 2003-06-09 | Carboxy protection strategy for acidic C-terminal amino acids in chemical ligation of oligopeptides |
CA002487378A CA2487378A1 (en) | 2002-06-10 | 2003-06-09 | Carboxy protection strategies for acidic c-terminal amino acids in chemical ligation of oligopeptides |
DE60303314T DE60303314T2 (en) | 2002-06-10 | 2003-06-09 | METHOD FOR CARBOXYL GROUP PROTECTION OF ACIDS C-TERMINAL AMINO ACIDS FOR CHEMICAL COMPOSITION OF OLIGOPEPTIDES |
AU2003280206A AU2003280206A1 (en) | 2002-06-10 | 2003-06-09 | Carboxy protection strategies for acidic c-terminal amino acids in chemical ligation of oligopeptides |
US10/517,392 US7566697B2 (en) | 2002-06-10 | 2003-06-09 | Carboxy protection strategies for acidic C-terminal amino acids in chemical ligation of oligopeptides |
EP03764091A EP1511760B1 (en) | 2002-06-10 | 2003-06-09 | Carboxy protection strategies for acidic c-terminal amino acids in chemical ligation of oligopeptides |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38782502P | 2002-06-10 | 2002-06-10 | |
US60/387,825 | 2002-06-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004007661A2 WO2004007661A2 (en) | 2004-01-22 |
WO2004007661A3 true WO2004007661A3 (en) | 2004-07-22 |
Family
ID=30115507
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2003/005473 WO2004007661A2 (en) | 2002-06-10 | 2003-06-09 | Carboxy protection strategies for acidic c-terminal amino acids in chemical ligation of oligopeptides |
Country Status (8)
Country | Link |
---|---|
US (1) | US7566697B2 (en) |
EP (1) | EP1511760B1 (en) |
JP (1) | JP4327718B2 (en) |
AT (1) | ATE316096T1 (en) |
AU (1) | AU2003280206A1 (en) |
CA (1) | CA2487378A1 (en) |
DE (1) | DE60303314T2 (en) |
WO (1) | WO2004007661A2 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1871403B1 (en) | 2005-03-31 | 2010-09-08 | Amylin Pharmaceuticals, Inc. | Compositions and methods for the control, prevention and treatment of eating disorders |
CA2612274A1 (en) * | 2005-06-16 | 2006-12-21 | Amylin Pharmaceuticals, Inc. | Side-chain extended ligation |
US8309522B2 (en) | 2007-02-05 | 2012-11-13 | Amylin Pharmaceuticals, Llc | Neuromedin and FN-38 peptides for treating psychiatric diseases |
JP2010537984A (en) * | 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 | Methods and intermediates for chemical synthesis of polypeptides and proteins |
WO2009032181A2 (en) * | 2007-09-04 | 2009-03-12 | Ipsen Pharma S.A.S. | Methods and intermediates for chemical synthesis of polypeptides and proteins |
US9073978B2 (en) * | 2011-03-10 | 2015-07-07 | Glytech, Inc. | Method for producing glycopeptide having sialyl sugar chain, sialyl sugar chain-added amino acid derivative to be used in same, and glycopeptide |
US9169287B2 (en) | 2013-03-15 | 2015-10-27 | Massachusetts Institute Of Technology | Solid phase peptide synthesis processes and associated systems |
Family Cites Families (1)
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 |
-
2003
- 2003-06-09 JP JP2004521045A patent/JP4327718B2/en not_active Expired - Fee Related
- 2003-06-09 WO PCT/IB2003/005473 patent/WO2004007661A2/en active IP Right Grant
- 2003-06-09 AU AU2003280206A patent/AU2003280206A1/en not_active Abandoned
- 2003-06-09 AT AT03764091T patent/ATE316096T1/en active
- 2003-06-09 EP EP03764091A patent/EP1511760B1/en not_active Expired - Lifetime
- 2003-06-09 CA CA002487378A patent/CA2487378A1/en not_active Abandoned
- 2003-06-09 DE DE60303314T patent/DE60303314T2/en not_active Expired - Lifetime
- 2003-06-09 US US10/517,392 patent/US7566697B2/en not_active Expired - Fee Related
Non-Patent Citations (8)
Title |
---|
A B CLIPPINGDALE ET AL.: "Peptide thioester preparation by FMOC solid phase peptide synthesis for use in native chemical ligation", JOURNAL OF PEPTIDE SCIENCE., vol. 6, no. 5, JOHN WILEY AND SONS LTD., GB, pages 225 - 234, XP009015362, ISSN: 1075-2617 * |
F AL-OBEIDI ET AL.: "Synthesis of beta- and gamma-fluorenylmethyl esters of respectively N-alpha-Boc-L-aspartic acid and N-alpha-Boc-L-glutamic acid", INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH., vol. 35, 1990, MUNKSGAARD, COPENHAGEN., DK, pages 215 - 218, XP002274979, ISSN: 0367-8377 * |
G C STELAKATOS ET AL.: "New methods in peptide synthesis. Part III. Protection of carboxyl group", JOURNAL OF THE CHEMICAL SOCIETY, SECTION C: ORGANIC CHEMISTRY., no. 13, 1966, CHEMICAL SOCIETY. LETCHWORTH., GB, pages 1191 - 1199, XP002274980, ISSN: 0022-4952 * |
M VILLAIN ET AL.: "Backbone isomerization at aspartic-, glutamic acid-cysteine ligation", JOURNAL OF PEPTIDE SCIENCE., vol. 8 (suppl.), 31 August 2002 (2002-08-31), JOHN WILEY AND SONS LTD., GB, pages s108, XP009015060, ISSN: 1075-2617 * |
M VILLAIN ET AL.: "Native chemical ligation with aspartic ang glutamic acids as C-terminal residues: scope and limitations.", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY., no. 17, 2003, WILEY-VCH, WEINHEIM., DE, pages 3267 - 3272, XP002274981, ISSN: 1434-193X * |
R B WOODWARD ET AL.: "The total synthesis of cyclosporin C", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 88, no. 4, 20 February 1966 (1966-02-20), AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., US, pages 852 - 853, XP002274978, ISSN: 0002-7863 * |
T M HACKENG ET AL.: "Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF USA., vol. 96, 1999, NATIONAL ACADEMY OF SCIENCE. WASHINGTON., US, pages 10068 - 10073, XP002940700, ISSN: 0027-8424 * |
Y S LEE ET AL.: "A convergent liquid-phase synthesis of salmon calcitonin", JOURNAL OF PEPTIDE RESEARCH., vol. 54, 1999, MUNKSGAARD, COPENHAGEN., DK, pages 328 - 335, XP002274977, ISSN: 0367-8377 * |
Also Published As
Publication number | Publication date |
---|---|
US20050261473A1 (en) | 2005-11-24 |
US7566697B2 (en) | 2009-07-28 |
CA2487378A1 (en) | 2004-01-22 |
WO2004007661A2 (en) | 2004-01-22 |
EP1511760A2 (en) | 2005-03-09 |
ATE316096T1 (en) | 2006-02-15 |
DE60303314T2 (en) | 2006-08-17 |
JP4327718B2 (en) | 2009-09-09 |
JP2005529188A (en) | 2005-09-29 |
AU2003280206A1 (en) | 2004-02-02 |
EP1511760B1 (en) | 2006-01-18 |
DE60303314D1 (en) | 2006-04-06 |
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