Expedient solid-phase synthesis of fluorogenic protease substrates using the 7-amino-4-carbamoylmethylcoumarin (ACC) fluorophore

…, F Leonetti, BJ Backes, DS Dauber…

Index: 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 , vol. 67, # 3 p. 910 - 915

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Citation Number: 99

Abstract

A highly efficient solid-phase synthesis method for the preparation of fluorogenic protease substrates based upon the bifunctional leaving group 7-amino-4-carbamoylmethylcoumarin (ACC) is reported. Methods for the large-scale preparation of the novel fluorogenic leaving- group ACC are provided (Scheme 1). Detailed procedures are also provided for loading a diverse set of amino acids to support-bound ACC in good yields and with minimal ...