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Merck
CN

49742

Sigma-Aldrich

N-(N-Glutaryl-L-phenylalanyl)-2-aminoacridone

≥98.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C27H25N3O5
CAS Number:
115930-63-7
Molecular Weight:
471.50
MDL number:
MFCD01863061
UNSPSC Code:
12352200
PubChem Substance ID:
329757514

Key Documents

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Assay

≥98.0% (HPLC)

form

powder

mp

272 °C (lit.)

solubility

DMF: soluble
DMSO: soluble

fluorescence

λex 398 nm; λem 440 nm in 0.1 M Tris pH 8.0 (fluoroescence decreases upon cleavage with α-chymotrypsin)

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

OC(=O)CCCC(=O)N[C@@H](Cc1ccccc1)C(=O)Nc2ccc3Nc4ccccc4C(=O)c3c2

InChI

1S/C27H25N3O5/c31-24(11-6-12-25(32)33)30-23(15-17-7-2-1-3-8-17)27(35)28-18-13-14-22-20(16-18)26(34)19-9-4-5-10-21(19)29-22/h1-5,7-10,13-14,16,23H,6,11-12,15H2,(H,28,35)(H,29,34)(H,30,31)(H,32,33)/t23-/m0/s1

InChI key

ARQVOICOWZVNEP-QHCPKHFHSA-N

Application

N-(N-Glutaryl-L-phenylalanyl)-2-aminoacridone is a fluorogenic substrate used to assay proteases/peptidases such as α-chymotrypsin and trypsin.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Analysis Note

In addition to the emission maximum at 440 nm, there is a lower maxima at 463 nm.

Other Notes

Substrate for the continuous assay of α-chymotrypsin at wavelengths 450/570nm

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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L Hedstrom
Biological chemistry, 377(7-8), 465-470 (1996-07-01)
Trypsin and chymotrypsin have similar tertiary structures, although very different substrate specificities. Trypsin hydrolyzes peptides at Lys/Arg residues while chymotrypsin recognizes large hydrophobic residues. Recent work has shown that trypsin is not converted into a protease with chymotrypsin-like activity when
J H Baustert et al.
Analytical biochemistry, 171(2), 393-397 (1988-06-01)
A direct and continuous kinetic method for the fluorometric determination of alpha-chymotrypsin and trypsin is described, and 2-aminoacridone (2-AA) is introduced as a promising new fluorophore in analytical biochemistry. N-Succinyl- and N-glutaryl-phenylalanine as well as N-benzoylarginine were coupled to 2-AA

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