Peptide immobilization

Inamori, K, Kyo, M., Matsukawa, K, Inoue, Y., Sonoda, T., Tatematsu, K, Tanizawa, K., Mori, T. and Katayama, Y. (2008) Optimal surface chemistry for peptide immobilization in on-chip phosphorylation analysis. Anal. Chem. 80, 643-650. 

Matsuda, Akutsu, et al. [141] carried out chemical fixation of GRGDSP onto a poly(vinyl alcohol) film which had been activated by carbonyl diimidazol in dimethylformamide. For comparison, fibronectin was also immobilized on a poly(vinyl alcohol) film by the same technique. Matsuda et al. found that bovine endothelial cells (ECs) adhered well to the peptide- and fibronectin-immobilized film furthermore, after a three-day incubation, aggregated ECs floated on nontreated PVA film, while the peptide-immobilized surface greatly enhanced cell spreading and growth, which surpassed that on fibronectin-bound PVA. 

Kugo et al. [152] studied the behavior of human fibroblast attachment to RGDS- and GRGDS-peptide-immobilized poly(y-methyl L-glutamate) (PMLG) film via three types of spacer group. 

Smith, M. C., Furman, T. C., Ingolia, T. D., and Pidgeon, C. (1988) Chelating peptide-immobilized metal ion affinity chromatography. A new concept in affinity chromatography for recombinant proteins. J. Biol. Chem. 263(15), 7211-7215. 

Key Words Peptide microarrays small-molecule microarrays small-molecule immobilization peptide immobilization chemoselective ligation. 

Calvacanti E A, Shapiro 1 M, Composto R 1, et al. (2002) RGD Peptides immobilized on a mechanically deformable surface promote osteoblast differentiation. 1 Bone Min Res 17 2130-2140... 

Lue, R. Y, Zhu, Q., Li, D. (2004). Site-specific peptide immobilization strategies for the rapid detection of kinase activity on microarrays. Site-specific immobilization of biotinylated proteins for protein microarray analysis. Enzymatic profiling system in a small-molecule microarray. Intein-mediated biotinylation of proteins and its application in a protein microarray. Developing site-specific immobilization strategies of peptides in a microarray. Methods Mol. Biol. 278, 191-204. 

Nakamura, C. Inuyama, Y. Shirai, K. Sugimoto, N. Miyake, J., Detection of porphyrin using a short peptide immobilized on a surface plasmon resonance sensor chip. Biosens. 

Poly(ethylene glycol) grafted on crosslinked polystyrene (PEG-PS) resin has often been used as a polymer support for chiral catalysts of reactions performed in aqueous media. Peptides immobilized to PEG-PS resin have been developed and used as a catalyst for direct asymmetric aldol reactions in aqueous media (Scheme 3.19) [42]. When tripeptide-supported PEG-PS 67 was used as chiral catalyst in the reaction between 70 and acetone, the corresponding aldol product 69 was obtained with 73% ee. Kudo further developed the one-pot sequential reaction of acidic deacetalization and enanhoselective aldol reaction by using an Amberhte and PEG-ST-supported peptide catalyst 67 [43]. The enantioenriched aldol product 72 was obtained in 74% isolated yield from acetal 70 in a one-pot reaction (Scheme 3.20). 

Figure 18. Possible binding mode of the dye rhodamine to peptides immobilized on polyethylene glycol-polystyrene beads the peptides bear acetoxymethyl (3,4) or acyl glycine (5) end groups. ...

This methodology has been developed for the synthesis of phosphine-substituted peptides immobilized on... 

Glyoxylylpeptides, peptides with an N-terminal glyoxylyl residue, suitable electrophilic components for hydrazone-or semicarbazone-based peptide ligation. The glyoxylyl residue is obtained by periodate oxidation of N-terminal Ser or Thr under neutral aqueous conditions. This moiety can also be used for peptide immobilization or the attachment of reporter groups [C. Olivier et al., Bioconj. Chem. 2003, 24, 430 J. Marik et al.. Methods Mol. Biol. 2005, 310, 217]. 

Table 1. The amount of peptide immobilized on the microspheres and zeta potentials of the microspheres...

The substrate was composed of synthetic peptides, immobilized to a mica surface. The etching enzyme was Staphylococcal serine V8 protease, an enzyme that recognizes either glutamic or aspartic acid residues in the peptide and digests the peptides carboxyl acid terminus [1]. The enzyme was immobilized to the apex of an AFM probe, and the enzyme functionalized tip was scanned across the surface, in solution (phosphate buffer). 

Similarly small protein ligands have been created by selection from randomized Protein A receptor domain nsing phage display selection techniques from about a 40-million-member library (69). The selected peptides, termed affibodies, were so stable that the peptides, immobilized on HiTrap NHS Sepharose, could be repetitively sanitized by treatment with 0.5 M sodium hydroxide. 

In the study involving surface functionalization by photoenol chemistry, we introduced a novel 2-formyl-3-methylphenoxy (FMP) motif which we found more efficient than the 2-methylbenzophenone (at least in the conditions we used) [PAU 12b]. In particular, we demonstrated that complete cycloaddition could take place in minutes. Therefore, we aimed at bringing an FMP derivative onto surfaces in order to carry out patterning experiments. Again, we S5uithesized a silane derivative which we coated onto silicon wafers and assessed the success of the reaction by XPS and ToF-SIMS. The former confirmed the presence of the FMP moiety and the success of the photoinduced ftmctionalization of a bromine-containing maleimide which can act as a pol5mierization initiator as we will describe below. We also showed by ToF-SIMS that it is possible to use the photoenol method in the fiamework of peptide immobilization. 

Another route towards biomolecular functionalisation of switchable cell culture carriers was proposed by Gramm et al. (2011). The thermo-responsive polymer poly (vinyl methyl ether) was blended with a small amount of the alternating copolymer of vinyl methyl ether and maleic anhydride. After electron beam cross-linking, stable films with a dry thickness of up to 70 nm were obtained. The introduced anhydride moieties allow for subsequent protein or peptide immobilization without toxic coupling agents. This concept was applied and further developed by Teich-mann et al. (2013). The impact of different adhesion-promoting molecules immobilised in different concentrations to the thermo-responsive coating was evaluated and compared. 

---