8.52309
Fmoc-ACA-OH
Novabiochem®
别名:
Fmoc-ACA-OH, 7-N-Fmoc-aminocoumarin-4-acetic acid
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关于此项目
经验公式（希尔记法）:
C26H19NO6
化学文摘社编号:
分子量:
441.43
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22
SMILES string
N(c4cc5[o][c](cc(c5cc4)CC(=O)O)=O)C(=O)OCC1c2c(cccc2)c3c1cccc3
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
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
Quality Level
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.
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.
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
存储类别
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
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