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Modified peptide derivatives conjugated at 2-hydroxyethylamine moieties

Assignee: Pfizer Inc
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Filing: 1991-09-27
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Granted: 1994-11-08
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Expires: 2011-09-27
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Abstract

Abstract A process is disclosed for site-directed chemical modification of peptides and proteins that consists of two steps; (a) selective oxidation of a 2-hydroxyethylamine moiety, -CH(NH2)-CH(OH)-, in the peptide or protein to generate an aidehyde, and (b) reaction of the new aldehyde with a second reagent to form a product in which the native biological properties of the peptide are augmented by new and useful properties conferred by the second reagent. Additionally, the invention pertains to certain specified types of product formed by the above process.

Inventors

  • 👤 Kieran F. Geoghegan

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 16:43
CPC Classifications
C; C07; C07K; C07K14/00; C07K14/435; C07K14/665; C07K14/695; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/62; C07K14/52; C07K14/54; C07K14/5421; C07K14/545; C07K14/575; C07K14/57509; A61K2121/00

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 57 words
A process for the conjugation of a functionally useful group to a peptide comprising (a) generating an aldehyde by oxidation of a 2-hydroxyethylamine structure, said 2 hydroxyethylamine structure being part of a hydroxylysine residue which is inserted into a synthetic peptide; (b) reacting said aldehyde generated in step (a) with a reagent containing a functionally useful group.
Claim 2
Dependent Claim 57 words
A process for the conjugation of a functionally useful group to a peptide comprising (a) generating an aldehyde by oxidation of a 2-hydroxyethylamine structure, said 2 hydroxyethylamine structure being part of a hydroxylysine residue which is inserted into a synthetic peptide; (b) reacting said aldehyde generated in step (a) with a reagent containing a functionally useful group.
Claim 3
Dependent Claim 11 words
The process of claim 1 wherein said reagent is a hydrazide.
Claim 4
Dependent Claim 14 words
The process of claim 1 wherein the oxidation of step (a) is periodate oxidation.
Claim 5
Dependent Claim 11 words
The process of claim 1 wherein said functional group is biotin.
Claim 6
Dependent Claim 12 words
The process of claim 1 wherein said functional group is lucifer yellow.
Claim 7
Dependent Claim 12 words
The process of claim 1 wherein said functional group is a chromophore.
Claim 8
Dependent Claim 12 words
The process of claim 1 wherein said functional group contains a radionuclide.
Claim 9
Dependent Claim 13 words
The process of claim 1 wherein said functional group is a fluorescent label.
Claim 10
Dependent Claim 12 words
The process of claim 1 wherein said functional group is a drug.
Claim 11
Dependent Claim 12 words
The process of claim 9 wherein said drug is a cytotoxic agent.
Claim 12
Dependent Claim 36 words
A peptide conjugate having the structure P1--NH--CH--CO--P2 wherein R is a group with useful functional properties and P1 and P2 respectively represent the remainder of the peptide sequence of the amino terminus and carboxy terminus respectively.
Claim 13
Dependent Claim 36 words
A peptide conjugate having the structure P1--NH--CH--CO--P2 wherein R is a group with useful functional properties and P1 and P2 respectively represent the remainder of the peptide sequence of the amino terminus and carboxy terminus respectively.

References Cited (Backward Citations)

US5132111A Cited
US4973666A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1997-11-07 1998-05-09 1998-11-08 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-11-07 2002-05-09 2002-11-08 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-11-07 2006-05-09 2006-11-08 $7700.00 Window Closed / Lapsed

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