Fmoc-ACA-OH

Fmoc-ACA-OH is a useful tool for the SPPS of AMC fluorogenic protease substrates by Fmoc SPPS. Fmoc-ACA-OH ^[1] must be first loaded onto a Wang-type resin. Any unreacted linker hydroxyls must be capped using acetic anhydride. Following Fmoc removal, the first amino acid should be coupled with HATU/collidine ^[2]. Insertion of ACA into the middle of a peptide provides fluorogenic substrates for endopeptidases ^[3]. Treatment of the ACC peptide obtained after TFA cleavage with an aqueous base causes facile decarboxylation and formation of the AMC peptide.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Chromogenic Labeling of Synthetic Peptides

Literature references

^[1] J. L. Harris, et al. (2000) Proc. Natl. Acad. Sci. USA, 97, 7754.
^[2] D. J. Maly, et al. (2002) J. Org. Chem., 67, 910.
^[3] C. M. Salisbury, et al. (2002) J. Am. Chem. Soc., 124, 14868.

Color (visual): white to slight yellow to light red
Appearance of substance (visual): powder
Identity (IR): passes test
Purity (TLC(CMA1)): ≥ 98 %
Assay (HPLC, area%): ≥ 95.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

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