A3282
5-Azido-2-nitrobenzoic acid N-hydroxysuccinimide ester
≥95%, powder
别名:
N-(5-Azido-2-nitrobenzoyloxy)succinimide, N-Succinimidyl 5-azido-2-nitrobenzoate
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关于此项目
经验公式（希尔记法）:
C11H7N5O6
化学文摘社编号:
分子量:
305.20
PubChem Substance ID:
UNSPSC Code:
12352106
Beilstein/REAXYS Number:
1555224
MDL number:
Assay:
≥95%
Form:
powder
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
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
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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.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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].
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
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
M Nagao et al.
Nihon Naibunpi Gakkai zasshi, 66(10), 1108-1116 (1990-10-20)
We characterized structurally the receptors for somatostatin in rat cerebral cortex by affinity labeling with [125I-Tyr1] somatostatin. [125I-Tyr1] somatostatin was cross-linked to cerebrocortical membranes using photoreactive cross-linker: N-5-azido-2-nitrobenzoyloxy-succinimide. Analysis by autoradiography revealed a broad band centered at Mr = 72,000
H Kwon et al.
Journal of muscle research and cell motility, 15(5), 555-562 (1994-10-01)
Reaction of rabbit skeletal muscle F-actin with the lysine-directed photolabile cross-linker, N-5-azido-2-nitrobenzoyloxy succinimide was limited to Lysine-328 and Lysine-326, with Lysine-328 being labelled to a greater extent. Photolysis of the modified actin enhanced the actin-activated MgATPase activity of filamentous scallop
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