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:
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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J F Clémence et al.
Bioconjugate chemistry, 6(4), 411-417 (1995-07-01)
To attain light-dependent functionalization of biocompatible materials, a photolabel-derivatized, bioactive laminin fragment has been synthesized, chemically characterized, and photoimmobilized. Covalent high-resolution patterning of the laminin fragment CDPGYIGSR to hydroxylated fluorinated ethylene propylene (FEP-OH), poly(vinyl alcohol), and glycophase glass has been
Y Doi et al.
FEBS letters, 301(1), 99-102 (1992-04-13)
It has been shown that the EGTA-resistant actin, one of the two actin molecules associated to gelsolin, can be predominantly cross-linked to gelsolin by benzophenone-4-maleimide (BPM), a photoaffinity-labeling reagent, which was conjugated to Cys-374 of actin prior to cross-linking (Doi
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| M9775-100MG | 04061831827316 |