Bioorthogonal metal-free click-ligation of cRGD-pentapeptide to alginate.
"Click" reactions have become very common and powerful ligation techniques, of which 1,3-dipolar cycloadditions have most frequently been employed. Since metal-mediated cycloadditions are incompatible in biomedical applications due to toxicity issues associated with transition metals like copper, metal-free variants provide important alternatives. The metal-free conjugation process is studied in detail with special emphasis put on the reaction progress. This report unfolds the first aqueous metal-free "click" conjugation of a cyclic RGD-pentapeptide with the biomacromolecule alginate, creating a "smart" bioactive polymer with potential applications in biomedicine.
Institut für Organische Chemie and Biomolekulares Wirkstoffzentrum (BMWZ), Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany.
Andreas
A
Krause
Andreas
A
Kirschning
Gerald
G
Dräger
D000464:Alginates / Q000737:chemistry*; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D020723:Glucuronic Acid / Q000737:chemistry; D006603:Hexuronic Acids / Q000737:chemistry; D008026:Ligation; D010456:Peptides, Cyclic / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry
D000464:Alginates; D006603:Hexuronic Acids; D010456:Peptides, Cyclic; D011108:Polymers; C507169:cyclic arginine-glycine-aspartic acid peptide; D003300:Copper; D020723:Glucuronic Acid