Fmoc-ACA-OH

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. Literature: Fields, G. B.; Noble, R. L. 1990; 35: 161-214. “Approaches to High Throughput Physical Organic Chemistry” Portal, C.; Bradley, M. Org. Biomol. Chem. (Emerging Areas) 2007; 5: 587-592.