Title:
ON-RESIN PEPTIDE CYCLIZATION
Document Type and Number:
WIPO Patent Application WO2006045483
Kind Code:
A3
Abstract:
Method of peptide synthesis, comprising the steps of a. synthesizing a peptide linked to a solid phase which peptide comprises at least one cysteine, homo- or nor-cysteine residue, which cysteine is protected in its side chain by a S-tert.butyl-sulphenyl group b. either coupling N-terminally a further amino acid having a 3,3'-dithio-(1-carboxy-propyl)-propionyl-radical on its Na or deprotecting the Na of the N-terminal amino acid and reacting the free Na with 3,3'-dithio-propionic acid imide to yield the corresponding Na-3,3'-dithio-(1-carboxy-propyl)-propionamide or deprotecting the Na of the N-terminal amino acid and reacting the free Na with a compound of formula IV R7-S-S-[CH2]2-COOH IV wherein R7 is aryl-, including heteronuclear aryl, or is aralkyl-, alkylaryl- or alkyl-, which may be further substituted with halogeno, amido, ester, carboxy or ether, and c. reacting the peptide with a S-tert.Butyl-sulphenyl-protection group removing reagent, and d. cyclizing the peptide by means of disulfide bond formation, preferably cyclizing the peptide in the presence of air and/or oxygen.
Inventors:
VARRAY STEPHANE (CH)
WERBITZKY OLEG (CH)
ZEITER THOMAS (CH)
WERBITZKY OLEG (CH)
ZEITER THOMAS (CH)
Application Number:
PCT/EP2005/011182
Publication Date:
July 13, 2006
Filing Date:
October 18, 2005
Export Citation:
Assignee:
LONZA AG (CH)
VARRAY STEPHANE (CH)
WERBITZKY OLEG (CH)
ZEITER THOMAS (CH)
VARRAY STEPHANE (CH)
WERBITZKY OLEG (CH)
ZEITER THOMAS (CH)
International Classes:
C07K1/04; C07K1/06; C07K7/06
Domestic Patent References:
| WO2005121164A1 | 2005-12-22 | |||
| WO2004092202A1 | 2004-10-28 | |||
| WO2003093302A2 | 2003-11-13 |
Foreign References:
| CN1500805A | 2004-06-02 |
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