A3282
5-Azido-2-nitrobenzoic acid N-hydroxysuccinimide ester
≥95%, powder
Synonyme(s) :
N-(5-Azido-2-nitrobenzoyloxy)succinimide, N-Succinimidyl 5-azido-2-nitrobenzoate
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A propos de cet article
Formule empirique (notation de Hill) :
C11H7N5O6
Numéro CAS:
Poids moléculaire :
305.20
PubChem Substance ID:
UNSPSC Code:
12352106
Beilstein/REAXYS Number:
1555224
MDL number:
Assay:
≥95%
Form:
powder
assay
≥95%
form
powder
reaction suitability
reagent type: cross-linking reagent
color
yellow to yellow-orange
solubility
ethyl acetate: 25 mg/mL, DMF: soluble
functional group
NHS ester
storage temp.
2-8°C
SMILES string
O=C(ON1C(CCC1=O)=O)C2=C(C=CC(N=[N+]=[N-])=C2)[N+]([O-])=O
InChI
1S/C11H7N5O6/c12-14-13-6-1-2-8(16(20)21)7(5-6)11(19)22-15-9(17)3-4-10(15)18/h1-2,5H,3-4H2
InChI key
FUOJEDZPVVDXHI-UHFFFAOYSA-N
Application
Photoactive, heterobifunctional cross-linking reagent. Typically, initial reaction couples via ester to primary amine by amide bond formation in the pH range 6.5-8.5. Second bonding occurs during UV irradiation (250-350 nm) via reactive nitrene. The latter bonding is rapid and non-specific.
Other Notes
Note that the nitro substituent provides an absorption band at a longer wavelength compared to simple aryl azide.
Disclaimer
Reducing agents such as thiols may reduce the azide to amine and should be avoided. Initial manipulations and coupling should be performed under reduced light.
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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S A McMahan et al.
Biochemistry, 33(40), 12092-12099 (1994-10-11)
In an effort to better understand protein-protein photoaffinity cross-linking using aryl azides, we have tested a number of factors influencing the cross-linking of the sigma 70 subunit of Escherichia coli RNA polymerase to core RNA polymerase. These factors include the
S Karrasch et al.
Biophysical journal, 65(6), 2437-2446 (1993-12-01)
Scanning force microscopy allows imaging of biological molecules in their native state in buffer solution. To this end samples have to be fixed to a flat solid support so that they cannot be displaced by the scanning tip. Here we
P R Buckland et al.
The Biochemical journal, 235(3), 879-882 (1986-05-01)
We have recently shown that the beta subunit of thyrotropin (TSH) can be cross-linked to the TSH receptor [Buckland, Strickland, Pierce & Rees Smith (1985) Endocrinology (Baltimore) 116, 2122-2124; Buckland, Strickland & Rees Smith (1985) Biochem. Soc. Trans. 13, 942-943].
Numéro d'article de commerce international
| Référence | GTIN |
|---|---|
| A3282-100MG | 04061833287262 |