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Fmoc-ACA is used for solid-phase syntheses of fluorogenic protease substrates based on 7-amino-4-carbamoylmethylcoumarin (ACC).
Fmoc-ACA can be loaded onto polystyrene Rink resin and requires three repeated couplings to achieve 89% substitution. The unreacted amine functionalities have to be capped using acetic anhydride.
(a) Rink amine resins (0.5 equiv.), DIC/HOBt, DCM/DMF (7:3 v/v), 3x 30 min, (b) Acetic Anhydride (20 equiv.), Pyridine (10 equiv.), 30 min, (c) Piperidine in DMF (1:4 v/v), 2x 5 min, 30 min.
Fmoc-ACA-OH is incorporated into peptides as Fluorogenic marker for protease substrates.
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Kasperkiewicz, Paulina; Poreba, Marcin; Snipas, Scott J.; Parker, Heather; Winterbourn, Christine C.; Salvesen, Guy S.; Drag, Marcin Proceedings of the National Academy of Sciences of the United States of America (2014), 111(7), 2518-2523.
Rut, Wioletta; Poreba, Marcin; Kasperkiewicz, Paulina; Snipas, Scott J.; Drag, Marcin Journal of Medicinal Chemistry (2018), 61(12), 5222-5234. DOI:10.1021/acs.jmedchem.8b00026.
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