M9775
4-(N-Maleimido)benzophenone
Synonym(s):
Benzophenone-4-maleimide
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About This Item
Empirical Formula (Hill Notation):
C17H11NO3
CAS Number:
Molecular Weight:
277.27
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
InChI
1S/C17H11NO3/c19-15-10-11-16(20)18(15)14-8-6-13(7-9-14)17(21)12-4-2-1-3-5-12/h1-11H
SMILES string
O=C1C=CC(=O)N1c2ccc(cc2)C(=O)c3ccccc3
InChI key
OZIZEXQRIOURIJ-UHFFFAOYSA-N
reaction suitability
reagent type: cross-linking reagent
solubility
chloroform: 50 mg/mL, DMF: soluble
storage temp.
2-8°C
Application
A heterobifunctional cross-linking reagent containing a sulfhydryl-specific group and a photo-active group. Typically, coupled initially by thioether to molecule containing free sulfhydryl buffered at pH 6.8 (6.5-7.0). Second bonding occurs during UV irradiation (250 nm) via diradical excited state. Benzophenones demonstrate greater specificity for C-H insertion and are more stable in water than analogous reagents. In general they are more efficient in attachment because they may be repeatedly irradiated; however, a more intense irradiation may be required. The benzophenone is not sensitive to reduction compared to analogous reagents.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Mayumi Tamura et al.
Biochemical and biophysical research communications, 390(3), 581-584 (2009-10-13)
Relatively weak interactions between galectins and their potential ligands can hinder identification of physiological lectin ligands using conventional methods such as affinity purification. We have employed a combination of cysteine mutagenesis with chemical crosslinking using a photoactivatable sulfhydryl reagent benzophenone-4-maleimide
K N Rajasekharan et al.
Archives of biochemistry and biophysics, 288(2), 584-590 (1991-08-01)
Experimental conditions which permit the exchange of smooth muscle 20-kDa light chain into skeletal muscle myosin are described. The hybridization does not result in the regulation of actin-activated ATPase activity of the hybrid myosin by smooth light chain phosphorylation. Further
Robert Ahrends et al.
Nucleic acids research, 34(10), 3169-3180 (2006-06-15)
To investigate protein-protein interaction sites in the DNA mismatch repair system we developed a crosslinking/mass spectrometry technique employing a commercially available trifunctional crosslinker with a thiol-specific methanethiosulfonate group, a photoactivatable benzophenone moiety and a biotin affinity tag. The XACM approach
Jessica DeLeon-Rangel et al.
FEBS letters, 587(7), 892-897 (2013-02-19)
The interaction of the membrane traversing stator subunits a and b of the rotary ATP synthase was probed by substitution of a single Cys into each subunit with subsequent Cu(2+) catalyzed cross-linking. Extensive interaction between the transmembrane (TM) region of
Y K Doi et al.
Biochemistry, 30(23), 5769-5777 (1991-06-11)
The interaction of pig plasma gelsolin (G) and actin (A) was examined by using photoreactive 4-maleimidobenzophenone-actin (BPM-actin) in which BPM was previously conjugated to Cys-374 of actin through the maleimide moiety. In the presence of micromolar [Ca2+], the major cross-linked
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