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Sigma-Aldrich

Fmoc-ACA-OH

Novabiochem®

Synonym(s):

Fmoc-ACA-OH, 7-N-Fmoc-aminocoumarin-4-acetic acid

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About This Item

Empirical Formula (Hill Notation):
C26H19NO6
CAS Number:
378247-75-7
Molecular Weight:
441.43
UNSPSC Code:
12352209
NACRES:
NA.22

Quality Level

200

product line

Novabiochem®

Assay

≥95.0% (HPLC)
≥98% (TLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

aromatic amine

storage temp.

2-8°C

InChI

1S/C26H19NO6/c28-24(29)11-15-12-25(30)33-23-13-16(9-10-17(15)23)27-26(31)32-14-22-20-7-3-1-5-18(20)19-6-2-4-8-21(19)22/h1-10,12-13,22H,11,14H2,(H,27,31)(H,28,29)

InChI key

RCUKLQDGAASIAX-UHFFFAOYSA-N

Related Categories

General description

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.

Analysis Note

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

To see the solvent systems used for TLC of Novabiochem® products please click here.

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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