2003
DOI: 10.1021/ja036417x
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Isolation of Protein Ligands from Large Peptoid Libraries

Abstract: The isolation of ligands for large numbers of proteins is an important goal in proteomics. Whereas peptide libraries are rich sources of protein-binding molecules, native peptides have certain undesirable properties, such as sensitivity to proteases that make them less than ideal for some applications. We report here the construction and characterization of large, chemically diverse combinatorial libraries of peptoids (N-substituted oligoglycines). A protocol for the isolation of specific protein-binding molec… Show more

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Cited by 206 publications
(279 citation statements)
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“…The development of peptoids (oligomers of N-alkyl glycine) as ligands for MDM2 has been pursued by both Appella and coworkers and Kodadek and coworkers 95,97 Structure-Based Design Approach. Appella and coworkers attempted to mimic the display of p53 side chains Phe19, Trp23, and Leu26 on a helical peptoid scaffold.…”
Section: Peptoidsmentioning
confidence: 99%
See 1 more Smart Citation
“…The development of peptoids (oligomers of N-alkyl glycine) as ligands for MDM2 has been pursued by both Appella and coworkers and Kodadek and coworkers 95,97 Structure-Based Design Approach. Appella and coworkers attempted to mimic the display of p53 side chains Phe19, Trp23, and Leu26 on a helical peptoid scaffold.…”
Section: Peptoidsmentioning
confidence: 99%
“…Recognizing the potential of proteomics for medicine and biology, 96 Bachhawat-Sikder and Kodadek have utilized peptoids as protein capture reagents. 97 Using microwaveassisted 98 combinatorial chemistry and on-bead screening to construct and assay large peptoid libraries, they identified a peptoid (41, Figure 20) that binds to a MDM2-maltose binding protein (MBP) fusion protein. To validate the hit, a resynthesized and purified sample was tested by isothermal titration calorimetry and found to have an IC 50 of 37 lM.…”
Section: Peptoidsmentioning
confidence: 99%
“…The submonomer method of peptoid synthesis introduced by Zuckermann, et al, 7 allows for considerable diversity to be incorporated into the construction of peptoid libraries due to the large number of commercially available primary amines. The submonomer method has been applied extensively in the creation of peptoid libraries [8][9][10][11][12] , and it has shown great versatility in incorporating a diverse set of amines 13, 14 and hydrazines 15 . The peptoid scaffold has been further modified to create ureapeptoids 16, 17 and incorporate a variety of chemoselective functionalities 18 .…”
mentioning
confidence: 99%
“…7 TentaGel Macrobeads (280-320 µm diameter from Rapp Polymere) consist of a hydrophobic polystyrene core derivatized with poly(ethylene glycol) chains. 65 These beads have good swelling properties in both organic and aqueous solvents and are mechanically robust.…”
Section: Resultsmentioning
confidence: 99%
“…4 The on-bead screening approach has been successfully applied to the identification of ligands for a large number of biological targets. [5][6][7][8][9][10] Limitations of the on-bead screening format include the requirement for soluble targets and nonspecific adsorption of the sample onto the solid phase, confounding the analysis of protein binding. The need for soluble targets is a drawback for drug discovery, but this does not detract from the search for novel ligands for diagnostic or proteomics applications, where the target is usually a soluble protein and the ligand is immobilized.…”
Section: Introductionmentioning
confidence: 99%