AnaSpec Developes AMC Resins for SPPS

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Topic: AnaSpec Developes AMC Resins for SPPS

anaspec
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posted 03-21-2012 04:46 PM

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).

For more information, please visit http://www.anaspec.com/products/promotions.asp?col=2&row=1

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