M9775
4-(N-Maleimido)benzophenone
Synonym(s):
Benzophenone-4-maleimide
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C17H11NO3
CAS Number:
Molecular Weight:
277.27
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
reaction suitability
reagent type: cross-linking reagent
solubility
chloroform: 50 mg/mL
DMF: soluble
storage temp.
2-8°C
SMILES string
O=C1C=CC(=O)N1c2ccc(cc2)C(=O)c3ccccc3
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
InChI key
OZIZEXQRIOURIJ-UHFFFAOYSA-N
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Jenny L Maki et al.
Biochemistry, 51(7), 1369-1379 (2012-02-07)
The SecA molecular nanomachine in bacteria uses energy from ATP hydrolysis to drive post-translational secretion of preproteins through the SecYEG translocon. Cytosolic SecA exists in a dimeric, "closed" state with relatively low ATPase activity. After binding to the translocon, SecA
Mayumi Tamura et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 130(10), 1375-1379 (2010-10-12)
We have employed a combination of cysteine mutagenesis and chemical crosslinking using a photoactivatable sulfhydryl reagent, benzophenone-4-maleimide, to obtain a covalent complex between human galectin-1 and a model glycoprotein ligand, asialofetuin. We previously obtained a crosslinked product when Lys(28) of
Z Y Wang et al.
The Journal of biological chemistry, 265(9), 4953-4957 (1990-03-25)
We have used in vitro mutagenesis to synthesize in Escherichia coli a recombinant rabbit skeletal troponin-C (designated as TnC57) in which Cys-98 was replaced with leucine, and Ala-57 in the C-helix of the N-terminal domain was replaced with cysteine. TnC57
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
Anders Myrhammar et al.
Scientific reports, 10(1), 20777-20777 (2020-11-29)
Radionuclide molecular imaging of cancer-specific targets is a promising method to identify patients for targeted antibody therapy. Radiolabeled full-length antibodies however suffer from slow clearance, resulting in high background radiation. To overcome this problem, a pretargeting system based on complementary
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