Specification
Description
Fmoc-ACA-OH is a useful tool for the SPPS of AMC fluorogenic protease substrates by Fmoc SPPS. Fmoc-ACA-OH must be first loaded onto a Wang-type resin. Any unreacted linker hydroxyls must be capped using acetic anhydride. Following Fmoc removal, the first amino acid should be coupled with HATU/collidine. Insertion of ACA into the middle of a peptide provides fluorogenic substrates for endopeptidases. Treatment of the ACC peptide obtained after TFA cleavage with an aqueous base causes facile decarboxylation and formation of the AMC peptide.
Synonyms
Fmoc-ACA-OH, 7-N-Fmoc-aminocoumarin-4-acetic acid
InChI
1S/C26H19NO6/c28-24(29)11-15-12-25(30)33-23-13-16(9-10-17(15)23)27-26(31)32-14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-10,12-13,22H,11,14H2,(H,27,31)(H,28,29)
InChI Key
RCUKLQDGAASIAX-UHFFFAOYSA-N
Application
Peptide synthesis.
Assay
≥95.0% (HPLC)
≥98% (TLC)
Functional Group
aromatic amine
Reaction Suitability
reaction type: Fmoc solid-phase peptide synthesis