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Fmoc-ACA-OH
Chemical name: 7-(9-Fluorenylmethyloxycarbonylamino)-coumarin-4-acetic acid
- Product code:RL-1170
- CAS No.:378247-75-7
- Formula:C26H19NO6
- Storage temperature:2-8°C
- Molecular weight:441.43 g/mol
- Purity :min. 98%
from €252.00
description
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.
references
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.
Salisbury, Cleo M.; Maly, Dustin J.; Ellman, Jonathan A. Journal of the American Chemical Society (2002), 124(50), 14868-14870. DOI:10.1021/ja027477q;
Maly, Dustin J.; Leonetti, Francesco; Backes, Bradley J.; Dauber, Deborah S.; Harris, Jennifer L.; Craik, Charles S.; Ellman, Jonathan A. Journal of Organic Chemistry (2002), 67(3), 910-915. DOI:10.1021/jo016140o;
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.
DOI:10.1073/pnas.1318548111;
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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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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