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.
AnaSpec, EGT Group has developed a novel solid support AMC resin for facile solid-phase synthesis of peptide-AMCs. As result, 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.
Fmoc-ACA-Wang resin, AMC resins preloaded with Asp (D) and Arg ® for use in SPPS, as well as Fmoc-ACA-OH are now available from AnaSpec.
1. Harris, JL. et al. Proc. Natl. Acad. Sci. USA 97, 7754 (2000).
2. Maly, DJ. et al. J. Org. Chem. 67, 910 (2002).
AnaSpec, Eurogentec Group
AnaSpec, Eurogentec Group (anaspec.com) is a leading provider of integrated proteomics and genomics solutions™ for worldwide life science research. AnaSpec offers expertise in peptides, detection reagents, antibodies, assay kits, amino acids, oligonucleotides, and qPCRs. AnaSpec carries a broad product line of biochemicals and reagents for basic research, high-throughput screening and drug discovery. AnaSpec also provides premier custom services including peptide synthesis, antibody production, assay development, fluorescent dyes, and oligonucleotide synthesis. AnaSpec is certified to ISO 9001:2008.