AMC Resins for SPPS


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, Eurogentecís 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.

Product

Size

Catalog #

Fmoc - Asp(tBu) - AMC Resin NEW

100 mg

250 mg

500 mg

1 g

64499-01

64499-025

64499-05

64499-1

Fmoc - Arg(Pbf) - AMC Resin NEW

100 mg

250 mg

500 mg

1 g

64497-01

64497-025

64497-05

64497-1

Fmoc - Val - AMC Resin NEW

100 mg

250 mg

500 mg

1 g

64512-01

64512-025

64512-05

64512-1

Fmoc-ACA NEW
7-N-Fmoc-aminocoumarin-4-acetic acid

100 mg

500 mg

64425-01

64425-05

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

References:

Harris, JL. et al. Proc. Natl. Acad. Sci. USA 97, 7754 (2000).
Maly, DJ. et al. J. Org. Chem. 67, 910 (2002).