Title:
PROCESS FOR THE SYNTHESIS OF PEPTIDES
Document Type and Number:
WIPO Patent Application WO2003093301
Kind Code:
A3
Abstract:
A process for the solid-phase synthesis of a peptide is provided which comprises attaching an alpha-nitrogen protected alpha-carboxy protected amino acid to a solid support via its side chain, removing the alpha-nitrogen protecting group, and assembling a peptide chain on said alpha-nitrogen. Also novel amino acid analogues and solid-phase supports are provided.
Inventors:
EVANS DAVID JOHN (GB)
ATHERTON ERIC (GB)
ATHERTON ERIC (GB)
Application Number:
PCT/GB2003/001925
Publication Date:
January 08, 2004
Filing Date:
May 02, 2003
Export Citation:
Assignee:
AVECIA LTD (GB)
EVANS DAVID JOHN (GB)
ATHERTON ERIC (GB)
EVANS DAVID JOHN (GB)
ATHERTON ERIC (GB)
International Classes:
C07C323/59; C07K1/00; C07K1/04; C07K1/06; C07K7/06; C07K7/64; (IPC1-7): C07K1/04; C07C271/22; C07K1/06; C07K7/64
Foreign References:
| US6008058A | 1999-12-28 | |||
| EP0519327A1 | 1992-12-23 |
Other References:
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; HAN, YONGXIN ET AL: "A new side-chain anchoring strategy for solid-phase synthesis of peptide acids with C-terminal cysteine", XP002258927, retrieved from STN Database accession no. 127:50990 CA
A BERNHARDT ET AL.: "The sold-phase synthesis of side-chain-phoshorylated peptide-4-nitroanilides", JOURNAL OF PEPTIDE RESEARCH., vol. 50, no. 8, August 1997 (1997-08-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 143 - 152, XP000659212, ISSN: 1397-002X
H M ZHONG ET AL.: "Solid-phase synthesis of arginine-containing peptides by guanidine attachment to a sulfonyl linker", JOURNAL OF ORGANIC CHEMISTRY., vol. 62, no. 26, 1997, AMERICAN CHEMICAL SOCIETY. EASTON., US, pages 9326 - 9330, XP002258924, ISSN: 0022-3263
A F SPATOLA ET AL.: "An approach to cyclic peptide libraries: reducing epimerization in medium sized rings during solid phase synthesis", TETRAHEDRON LETTERS., vol. 37, no. 5, 1996, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 591 - 594, XP004030307, ISSN: 0040-4039
C CABRELE ET AL.: "Amino acid side chain attachment approach and its application to the synthesis of tyrosine-containing cyclic peptides", JOURNAL OF ORGANIC CHEMISTRY., vol. 64, no. 12, 1999, AMERICAN CHEMICAL SOCIETY. EASTON., US, pages 4353 - 4361, XP002258925, ISSN: 0022-3263
J ALSINA ET AL.: "Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides", TETRAHEDRON LETTERS., vol. 38, no. 5, 1997, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 883 - 886, XP004017038, ISSN: 0040-4039
P ROMANOVSKIS & A SPATOLA: "Preparation of head-to-tail cyclic peptides via side-chain attachment: implications for library synthesis", JOURNAL OF PEPTIDE RESEARCH., vol. 52, no. 11, November 1998 (1998-11-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 356 - 374, XP000788443, ISSN: 1397-002X
CABRELE, CHIARA ET AL: "Amino acid side chain attachment: a convenient strategy to obtain C-terminally modified or cyclic peptides by solid phase synthesis", PEPTIDES 1998, PROCEEDINGS OF THE EUROPEAN PEPTIDE SYMPOSIUM, 25TH, BUDAPEST, AUG. 30-SEPT. 4, 1998 (1999), MEETING DATE 1998, 202-203. EDITOR(S): BAJUSZ, SANDOR;HUDECZ, FERENC. PUBLISHER: AKADEMIAI KIADO, BUDAPEST, HUNG., 1999, XP002258926
A BERNHARDT ET AL.: "The sold-phase synthesis of side-chain-phoshorylated peptide-4-nitroanilides", JOURNAL OF PEPTIDE RESEARCH., vol. 50, no. 8, August 1997 (1997-08-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 143 - 152, XP000659212, ISSN: 1397-002X
H M ZHONG ET AL.: "Solid-phase synthesis of arginine-containing peptides by guanidine attachment to a sulfonyl linker", JOURNAL OF ORGANIC CHEMISTRY., vol. 62, no. 26, 1997, AMERICAN CHEMICAL SOCIETY. EASTON., US, pages 9326 - 9330, XP002258924, ISSN: 0022-3263
A F SPATOLA ET AL.: "An approach to cyclic peptide libraries: reducing epimerization in medium sized rings during solid phase synthesis", TETRAHEDRON LETTERS., vol. 37, no. 5, 1996, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 591 - 594, XP004030307, ISSN: 0040-4039
C CABRELE ET AL.: "Amino acid side chain attachment approach and its application to the synthesis of tyrosine-containing cyclic peptides", JOURNAL OF ORGANIC CHEMISTRY., vol. 64, no. 12, 1999, AMERICAN CHEMICAL SOCIETY. EASTON., US, pages 4353 - 4361, XP002258925, ISSN: 0022-3263
J ALSINA ET AL.: "Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides", TETRAHEDRON LETTERS., vol. 38, no. 5, 1997, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM., NL, pages 883 - 886, XP004017038, ISSN: 0040-4039
P ROMANOVSKIS & A SPATOLA: "Preparation of head-to-tail cyclic peptides via side-chain attachment: implications for library synthesis", JOURNAL OF PEPTIDE RESEARCH., vol. 52, no. 11, November 1998 (1998-11-01), MUNKSGAARD INTERNATIONAL PUBLISHERS, COPENHAGEN., DK, pages 356 - 374, XP000788443, ISSN: 1397-002X
CABRELE, CHIARA ET AL: "Amino acid side chain attachment: a convenient strategy to obtain C-terminally modified or cyclic peptides by solid phase synthesis", PEPTIDES 1998, PROCEEDINGS OF THE EUROPEAN PEPTIDE SYMPOSIUM, 25TH, BUDAPEST, AUG. 30-SEPT. 4, 1998 (1999), MEETING DATE 1998, 202-203. EDITOR(S): BAJUSZ, SANDOR;HUDECZ, FERENC. PUBLISHER: AKADEMIAI KIADO, BUDAPEST, HUNG., 1999, XP002258926
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