US4914151A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Resin-linker combination for the solid-phase synthesis of peptides and intermediates
Assignee: Bachem Holding AG
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Filing: 1989-03-29
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Granted: 1990-04-03
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Expires: 2009-03-29
Abstract
Abstract The present invention relates to a novel polymeric carrier, a process for its production and its use for the preparation of peptides and their intermediates. The process comprises reacting chloromethylated polystyrene (cross-linked with divinylbenzene) with a 4-hydroxy-2-substituted-benzyl alcohol (linker), attaching α-amino acids with amino and side-chain protection to the carrier thus obtained, and building up a peptide according to the method known in the field of solid phase peptide synthesis (SPPS). The method allows removal of intermediates or final products under extremely mild acidic conditions giving products in high state of purity and yield. The 2-substituent consists of an electron donating group, such as methoxy.
Inventors
- 👤 Monika Mergler
- 👤 Jacques Gosteli
- 👤 Peter Grogg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 17:34
CPC Classifications
C; C08; C08F; C08F8/00; C07; C07K; C07K1/00; C07K1/04; C07K1/042; C08F8/26; C08F8/30; C08F2800/00; C08F2800/20; Y; Y10; Y10S; Y10S530/00; Y10S530/81; Y10S530/812; Y10S530/815
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
78 words
Peptidylresin fragments consisting of a polymer having the formula IV: ##STR5## cross-linked with 0.5-2.0% of divinylbenzene optionally substituted by halogen or lower alkyl, in which R represents a lower alkoxy, lower alkylthio or a ##STR6## group, in which R 1 and R 2 stand for lower alkyl, and Y represents the residue of an amino acid or peptide of which the carboxyl group is condensed in ester manner and in which the functional groups may optionally be protected.
Claim 2
Dependent Claim
78 words
Peptidylresin fragments consisting of a polymer having the formula IV: ##STR5## cross-linked with 0.5-2.0% of divinylbenzene optionally substituted by halogen or lower alkyl, in which R represents a lower alkoxy, lower alkylthio or a ##STR6## group, in which R 1 and R 2 stand for lower alkyl, and Y represents the residue of an amino acid or peptide of which the carboxyl group is condensed in ester manner and in which the functional groups may optionally be protected.
Claim 3
Dependent Claim
42 words
Fragments according to claim 1 consisting of a polymer of formula IV, in which R is lower alkoxy and Y represents the residue of a naturally occurring α-amino acid or their enantiomers (D-series), homologs and isomers with its functional groups optionally protected.
Claim 4
Dependent Claim
34 words
Fragments according to claim 1 consisting of a polymer of formula IV, in which R is methoxy and Y represents the residue of a naturally occurring α-amino acid with its functional groups optionally protected.
Claim 5
Dependent Claim
40 words
Fragments according to claim 1 consisting of a polymer of formula IV, in which R is methoxy and Y represents the residue of a naturally occurring α-amino acid and in which the α-amino group is blocked by the Fmoc-group (9-fluorenylmethyloxycarbonyl).
Claim 6
Dependent Claim
23 words
A fragment according to claim 1 consisting of a polymer of formula IV, in which R is methoxy and Y represents the Ala-residue.
Claim 7
Dependent Claim
23 words
A fragment according to claim 1 consisting of a polymer of formula IV, in which R is methoxy and Y represents the Arg-residue.
Claim 8
Dependent Claim
23 words
A fragment according to claim 1 consisting of a polymer of formula IV, in which R is methoxy and Y represents the Asn-residue.
Claim 9
Dependent Claim
23 words
A fragment according to claim 1 consisting of a polymer of formula IV, in which R is methoxy and Y represents the Gln-residue.
Claim 10
Dependent Claim
23 words
A fragment according to claim 1 consisting of a polymer of formula IV, in which R is methoxy and Y represents the Gly-residue.
Claim 11
Dependent Claim
140 words
A process for synthesizing peptides using a peptidylresin consisting of a polymer having the formula: ##STR7## ##STR8## cross-linked with 0.5-2.0% of divinylbenzene, in which R represents a lower alkoxy, lower alkylthio or a ##STR9## group, in which R 1 and R 2 stand for lower alkyl, the polymer being cross-linked with 0.5-2.0% divinylbenzene optionally substituted by halogen or lower alkyl, and Y represents the residue of an amino acid or peptide of which the carboxyl group is condensed resin-linker in ester manner and in which the functional groups may optionally be protected, the carboxy-terminal amino group of the residue being protected by a masking group, the process comprising: cleaving the masking group from the carboxy-terminal amino group to form an intermediate resin linker, and subsequently coupling the intermediate resin linker with an amino acid having a protected carboxy-terminal amino group.
Claim 12
Dependent Claim
140 words
A process for synthesizing peptides using a peptidylresin consisting of a polymer having the formula: ##STR7## ##STR8## cross-linked with 0.5-2.0% of divinylbenzene, in which R represents a lower alkoxy, lower alkylthio or a ##STR9## group, in which R 1 and R 2 stand for lower alkyl, the polymer being cross-linked with 0.5-2.0% divinylbenzene optionally substituted by halogen or lower alkyl, and Y represents the residue of an amino acid or peptide of which the carboxyl group is condensed resin-linker in ester manner and in which the functional groups may optionally be protected, the carboxy-terminal amino group of the residue being protected by a masking group, the process comprising: cleaving the masking group from the carboxy-terminal amino group to form an intermediate resin linker, and subsequently coupling the intermediate resin linker with an amino acid having a protected carboxy-terminal amino group.
References Cited (Backward Citations)
US4085261A
Cited
US4173693A
Cited
US4446285A
Cited
US4725568A
Cited
EP0200404A2
Cited
US4755558A
Cited
US4786684A
Cited
US4764595A
Cited
US4762881A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-04-02 | 1993-10-02 | 1994-04-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-04-02 | 1997-10-02 | 1998-04-03 | $3760.00 | Window Closed / Lapsed |
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