Peptide-7-amino-4-methylcoumarin conjugates (peptide-AMCs) are widely used as fluorogenic substrates to study proteases. The preparation of peptide-AMCs usually involves solution phase synthesis since AMC lacks an additional functional group for attachment to a solid support. Although solid-phase peptide synthesis (SPPS) of peptide-7-amino-4-carbamoylmethylcoumarin conjugates (peptide-ACCs) as an alternative for peptide-AMCs has been previously reported;^1,2 no AMC solid support resin for SPPS has ever been reported - until now.

AnaSpec, Eurogentec’s newest North American division, is pleased to announce the development of a novel solid support AMC resin for facile solid-phase synthesis of peptide-AMCs. As shown in Figure 1, N-Fmoc-7-aminocoumarin-4-acetic acid (Fmoc-Aca-OH) is attached to Wang resin as a linker. After Fmoc removal, peptides are synthesized on the amino group of the linker using standard SPPS Fmoc chemistry, followed by cleavage with trifluoroacetic acid. The crude peptide-7-aminocoumarin-4-acetic acid conjugates (peptide-ACAs) undergo facile decarboxylation under mild conditions to afford peptide-AMCs.

Figure 1. Solid-phase synthesis of peptide-AMCs using AMC resin

AMC resins preloaded with Asp (D) and Arg (R) for use in SPPS, as well as Fmoc-ACA-OH are now only available from AnaSpec.

Contact service@anaspec.com to request other pre-loaded AMC resins.

View the poster presented at the 2010 ABRF Meeting in Sacramento, CA on Mar 21, 2010 entitled “Facile Solid-Phase Synthesis of Peptide-7-amino-4-methylcoumarin Conjugates (Peptide-AMCs) Using a Novel AMC Resin”