Fremont CA – February 13, 2012 -- 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.
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 (R) for use in SPPS, as well as Fmoc-ACA-OH are now available from AnaSpec.
References:
1. Harris, JL. et al. Proc. Natl. Acad. Sci. USA 97, 7754 (2000).
2. Maly, DJ. et al. J. Org. Chem. 67, 910 (2002).
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AnaSpec, Eurogentec Group
AnaSpec, Eurogentec Group is a leading provider of integrated proteomics and genomics solutionsTM 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.
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