US5545698A
Expired / Lapsed
US
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Polyethylene glycol derivatives for solid-phase applications
Assignee: University of Minnesota Twin Cities
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Filing: 1993-11-10
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Granted: 1996-08-13
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Expires: 2013-11-10
Abstract
Abstract The present invention pertains to polyethylene glycol (PEG) derivatized graft supports, to methods for making these supports and to methods of using the supports to synthesize peptides by solid-phase synthesis techniques. The PEG-graft supports of this invention comprise functionalized PEG derivatives which are covalently attached to solid supports, such as polystyrene.
Inventors
- 👤 George Barany
- 👤 Fernando Albericio
- 👤 Nuria A. Sol e
- 👤 Jane Chang
- 👤 Samuel Zalipsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 12:52
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/04; C07K1/042; C08; C08F; C08F8/00
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
92 words
A resin for solid-phasepeptide synthesis represented by the general formula: ##STR8## wherein Y is a diamino monocarboxylate moiety that optionally can be protected by an N.sup.ω protecting group; n is an integer from about 5 to about 150; SS is a solid support; A is a straight chain or branched C1-C10 alkyl group; B is a single bond or-(CR 6 R 7 ) m - N(H)C(O)- where m is 1 to 4; and R 1 to R 7 are independently selected from the group consisting of hydrogen, alkyl groups and aryl groups.
Claim 2
Dependent Claim
92 words
A resin for solid-phasepeptide synthesis represented by the general formula: ##STR8## wherein Y is a diamino monocarboxylate moiety that optionally can be protected by an N.sup.ω protecting group; n is an integer from about 5 to about 150; SS is a solid support; A is a straight chain or branched C1-C10 alkyl group; B is a single bond or-(CR 6 R 7 ) m - N(H)C(O)- where m is 1 to 4; and R 1 to R 7 are independently selected from the group consisting of hydrogen, alkyl groups and aryl groups.
Claim 3
Dependent Claim
26 words
The resin of claim 1 wherein the solid support is selected from the group consisting of amino-functional membranes, porous glass, silica, polystyrenes, polydimethylacrylamides, cotton and paper.
Claim 4
Dependent Claim
28 words
The resin of claim 2 wherein the solid support comprises a polystyrene selected from the group consisting of amino-polystyrene, aminomethyl polystyrene, aminoacyl polystyrene, benzhydrylamine polystyrene and p-methylbenzhydrylamine polystyrene.
Claim 5
Independent Claim
75 words
A method of producing a resin for solid-phase peptide synthesis, comprising the steps of: (a) coupling a bifunctional compound having a poly(oxyethylene) core and carboxyl end groups to an amino-functionalized solid support under conditions sufficient for one of the carboxyl groups on the bifunctional compound to react with the amino groups on the solid support; and (b) introducing an amino functionality to replace the pendant terminal carboxyl group of the resin formed in step a.
Claim 6
Independent Claim
75 words
A method of producing a resin for solid-phase peptide synthesis, comprising the steps of: (a) coupling a bifunctional compound having a poly(oxyethylene) core and carboxyl end groups to an amino-functionalized solid support under conditions sufficient for one of the carboxyl groups on the bifunctional compound to react with the amino groups on the solid support; and (b) introducing an amino functionality to replace the pendant terminal carboxyl group of the resin formed in step a.
Claim 7
Dependent Claim
27 words
The method of claim 4 wherein the bifunctional compound is produced by reacting amino groups on a poly(oxyethylene) diamine polymer with a dicarboxylic acid or an anhydride.
Claim 8
Dependent Claim
107 words
The method of claim 4 wherein the product of step (a) is represented by the general formula: ##STR9## wherein n is an integer from about 5 to about 150; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of H, alkyl groups and aryl groups; X is selected from the group consisting of OH, halogens, or the activating group of an active ester or thioester; and A is selected from the group consisting of straight chain or branched alkyl groups having up to about 10 carbon atoms, CH═CH groups and aromatic groups.
Claim 9
Independent Claim
65 words
A method of producing a resin for solid-phase peptide synthesis, comprising the steps of: a) providing a solid support having attached thereto a diamino monocarboxylate having two N.sup.ω -amino protecting groups: b) removing a protecting group from one of the two N.sup.ω -amino moieties; and c) coupling a monofunctional carboxyl terminal polyethylene glycol derivative to the deprotected N.sup.ω -amino group to thereby produce the resin.
Claim 10
Independent Claim
65 words
A method of producing a resin for solid-phase peptide synthesis, comprising the steps of: a) providing a solid support having attached thereto a diamino monocarboxylate having two N.sup.ω -amino protecting groups: b) removing a protecting group from one of the two N.sup.ω -amino moieties; and c) coupling a monofunctional carboxyl terminal polyethylene glycol derivative to the deprotected N.sup.ω -amino group to thereby produce the resin.
Claim 11
Dependent Claim
94 words
The method of claim 7 wherein the resin is represented by the formula: ##STR10## wherein Y is a diamino monocarboxylate moiety that optionally can be protected by a N.sup.ω protecting group; n is an integer from about 5 to about 150; SS is a solid support; A is a straight chain or branched C1-C10 alkyl group; B is a single bond or -(CR 6 R 7 ) m -N(H)C(O)-where m is 1 to 4; and R 1 to R 7 are independently selected from the group consisting of hydrogen, alkyl groups and aryl groups.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1999-08-13 | 2000-02-12 | 2000-08-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2003-08-13 | 2004-02-12 | 2004-08-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2007-08-13 | 2008-02-12 | 2008-08-13 | $7700.00 | Window Closed / Lapsed |