Benzylprotected aromatic phosphonic acids for anchoring peptides on titanium.
The development of biocompatible coatings is an ongoing issue. Mimicking the physiological adhesion process of osteoblasts to the extracellular matrix improves cell adhesion of osteoblasts in vitro and results in improved and earlier osseous integration of implants in vivo. Titanium, an often used material in implant surgery, can be easily coated by peptides bearing phosphonic acid groups. We report here, the synthesis of benzyl protected phosphonic acids suitable for solid-phase peptide synthesis (SPPS), which can be easily deprotected with TFA.
Auernheimer
Jörg
J
Department Chemie, Lehrstuhl II f. Organische Chemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.
Kessler
Horst
H
D000818:Animals; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry*; D002448:Cell Adhesion / Q000187:drug effects; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry*; D051379:Mice; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D010006:Osteoblasts / Q000187:drug effects; D012821:Silanes / Q000737:chemistry; D014025:Titanium / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry
D001565:Benzoates; D006841:Hydrocarbons, Aromatic; D009842:Oligopeptides; D063065:Organophosphonates; D012821:Silanes; D014025:Titanium; D014269:Trifluoroacetic Acid