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08450

Sigma-Aldrich

7-Amino-4-methyl-3-coumarinacetic acid N-succinimidyl ester

BioReagent, suitable for fluorescence, ≥90% (HPLC)

Synonym(s):

7-(Dimethylamino)coumarin-4-acetic acid-NHS, 7-Amino-4-methyl-3coumarinylacetyl, N-Succinimidyl 7-amino-4-methyl-3-coumarinylacetate, AMCA-NHS, Succinimidyl-7-amino-4-methylcoumarin-3-acetate

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About This Item

Empirical Formula (Hill Notation):
C16H14N2O6
CAS Number:
113721-87-2
Molecular Weight:
330.29
Beilstein:
9007679
MDL number:
MFCD00036170
UNSPSC Code:
12352108
PubChem Substance ID:
329748586
NACRES:
NA.32

product line

BioReagent

Assay

≥90% (HPLC)

solubility

DMF: soluble
DMSO: soluble

fluorescence

λex 354 nm; λem 440 nm in methanol

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

CC1=C(CC(=O)ON2C(=O)CCC2=O)C(=O)Oc3cc(N)ccc13

InChI

1S/C16H14N2O6/c1-8-10-3-2-9(17)6-12(10)23-16(22)11(8)7-15(21)24-18-13(19)4-5-14(18)20/h2-3,6H,4-5,7,17H2,1H3

InChI key

ILKQVTIMOGNSAS-UHFFFAOYSA-N

Application

AMCA-NHS has been utilized in the development of a donor europium chelate fluorochrome for use in LRET based analyses by first reacting with an amino group and then with DTPA anhydride . Utilized in FRET based studies, acting as the donor dye and can be paired with fluorescein-5-isothiocyanate as the acceptor dye . A blue fluorescent dye reactive towards primary amine groups on proteins, peptides, antibodies, and other biomolecules (at pH 7.0-9.0).

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Labeling of lysyl residues in proteins

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - 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

Certificates of Analysis (COA)

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H I Stefanova et al.
Biochemistry, 32(1), 356-362 (1993-01-12)
The (Ca(2+)-Mg2+)-ATPase of sarcoplasmic reticulum was labeled with the succinimidyl ester of 7-amino-4-methylcoumarin-3-acetic (AMCA). Although a large number of residues were labeled, it was found that Lys-492 was labeled preferentially at pH values between 6 and 8, consistent with an

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