A peptide‐based coating toolbox to enable click chemistry on polymers, metals, and silicon through sortagging

Abstract

A versatile peptide‐based toolbox for surface functionalization was established by a combination of a universal material binding peptide (LCI‐anchor peptide) and sortase‐mediated bioconjugation (sortagging). This toolbox facilitates surface functionalization either as a one‐ or a two‐step strategy. In the case of the one‐step strategy, the desired functionality was directly introduced to LCI. For the two‐step strategy, LCI was modified with a reactive group, which can be further functionalized (e.g., employing “click” chemistry). Sortagging of LCI, employing sortase A from Staphylococcus aureus, was achieved with six different amine compounds: dibenzocyclooctyne amine, biotin‐polyethylene glycol amine, Cyanine‐3 amine, kanamycin, methoxypolyethylene glycol amine (Mn = 5000 Da), and 2,2,3,3,4,4,4‐Heptafluorobutylamine. The purification of LCI‐amine sortagging products was performed by a negative purification using Strep‐tag II affinity chromatography, resulting in LCI‐amine conjugates with purities >90%. For the two‐step strategy, the LCI‐dibenzocyclooctyne sortagging product was purified and enabled, through copper‐free azide–alkyne “click” chemistry, universal surface functionalization of material surfaces such as polypropylene, polyethylene terephthalate, stainless steel, gold, and silicon. The click reaction was performed before or after surface binding of LCI‐dibenzocyclooctyne. Finally, in the case of the one‐step strategy, polypropylene was directly functionalized with Cyanine‐3 and biotin‐polyethylene glycol amine.

Empowering Site‐Specific Bioconjugations In Vitro and In Vivo: Advances in Sortase Engineering and Sortase‐Mediated Ligation

“…Subsequently, LCI‐DBCO adhered to different materials such as polypropylene, polystyrene, gold, stainless steel, and silicon. By conducting the click reaction between surface‐bound LCI‐DBCO and a fluorescent Cy‐3 azide, the samples coated with LCI‐DBCO exhibited up to 3.9‐fold higher fluorescence intensity compared to the corresponding controls [101] . These results highlight the versatility of the surface functionalization approach, paving the way for novel coatings with unique properties.…”

“…For instance, the utilization of sortase‐click technology empowered the synthesis of noncanonical N‐to‐N and C‐to‐C fused protein dimers [98] . The combination with material binding peptides and sortase‐click technology has opened new avenues of SML application in material science [101] . The integration of UAA, bioorthogonal Staudinger reduction, and SML has led to the development of a novel methodology called “Sortylation”, proving to be a powerful tool in biorthogonal applications [102,104] .…”

Ein modifiziertes Ankerpeptid LCI mit einem Cobalt‐Cofaktor verbessert die Oxidationseffizienz von Polystyrol‐Mikropartikeln

“…[13][14][15] Wie bereits gezeigt wurde, bindet das β-Faltblatt-Ankerpeptid LCI ("liquid chromatography peak I") spezifisch und effizient an etliche Polymeroberflächen wie Polystyrol unter milden Bedingungen. [16][17][18][19][20][21][22][23][24] Da ein Gramm Ankerpeptid ausreicht, eine Oberfläche von bis zu 654 m 2 mit einer Monolage zu beschichten, [25] bieten Ankerpeptide eine skalierbare, einfache und kostengünstige Funktionalisierungsmethode durch Sprühen und Tauchbeschichtung. [25][26][27][28] Metallorganische Katalysatoren ermöglichen die selektive Oxidation von CÀ H-Bindungen kleiner Alkanmoleküle durch unterschiedliche Oxidationsmittel, [29][30][31][32][33][34][35][36][37][38][39][40][41] was bei Polyolefinen jedoch nur in begrenztem Umfang funktioniert.…”

Hexyl Gallate Loaded Microgels Enable Efficient Protection Against Citrus Canker

“…Some anchor peptides, such as hDerm, may exhibit antibacterial effects, or they can even functionalize other reactions, which can be referred to as multifunctional peptides. [51][52][53] However, when tested alone against X. citri cells, at the highest concentration of 200 μg mL −1 , hDerm did not show any antimicrobial effect against this plant pathogen (Figure S22, Supporting Information).…”