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.
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.
to request other pre-loaded AMC resins.
View the poster
presented at the 2010 ABRF Meeting in Sacramento, CA on Mar 21, 2010 entitled
Synthesis of Peptide-7-amino-4-methylcoumarin Conjugates (Peptide-AMCs) Using
a Novel AMC Resin”
Harris, JL. et al. Proc. Natl. Acad. Sci. USA 97,
Maly, DJ. et al. J. Org. Chem. 67, 910 (2002).