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A3282

Sigma-Aldrich

5-Azido-2-nitrobenzoic acid N-hydroxysuccinimide ester

≥95%, powder

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Synonym(s):
N-(5-Azido-2-nitrobenzoyloxy)succinimide, N-Succinimidyl 5-azido-2-nitrobenzoate
Empirical Formula (Hill Notation):
C11H7N5O6
CAS Number:
Molecular Weight:
305.20
Beilstein:
1555224
MDL number:
PubChem Substance ID:

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

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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.

Caution

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.

Other Notes

Note that the nitro substituent provides an absorption band at a longer wavelength compared to simple aryl azide.

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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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].
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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