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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Yoichiro Arata et al.
Biochemistry, 41(37), 11301-11307 (2002-09-11)
Using a combination of cysteine mutagenesis and covalent cross-linking, we have identified subunits in close proximity to specific sites within subunit B of the vacuolar (H(+))-ATPase (V-ATPase) of yeast. Unique cysteine residues were introduced into subunit B by site-directed mutagenesis
T Tao et al.
Archives of biochemistry and biophysics, 240(2), 627-634 (1985-08-01)
The site-specific photocrosslinker, benzophenone-4-maleimide, was used to label G-actin specifically at Cys-374, the penultimate residue from the C terminus. The resultant BP-G-actin was polymerized to form BP-F-actin, and both forms of actin were irradiated to activate the benzophenone moiety. We
Mayumi Tamura et al.
Biological & pharmaceutical bulletin, 34(6), 929-932 (2011-06-02)
LEC-1 is the first tandem repeat-type galectin isolated from an animal system; this galectin has two carbohydrate recognition domains in a single polypeptide chain. Because its two lectin domains have different sugar-binding profiles, these domains are thought to interact with
Y Luo et al.
Journal of molecular biology, 296(3), 899-910 (2000-03-15)
The interaction sites of rabbit skeletal troponin I (TnI) with troponin C (TnC), troponin T (TnT), tropomyosin (Tm) and actin were mapped systematically using nine single cysteine residue TnI mutants with mutation sites at positions 6, 48, 64, 89, 104
S Basu et al.
The Biochemical journal, 296 ( Pt 3), 577-583 (1993-12-15)
Treatment of murine leukaemia virus reverse transcriptase with benzophenone 4-maleimide inactivates DNA polymerase activity, but has no effect on the RNAase H function. Kinetic measurements indicated that benzophenone 4-maleimide is a competitive inhibitor with respect to template-primer binding, but is
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