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Merck
CN

A3282

Sigma-Aldrich

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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About This Item

经验公式(希尔记法):
C11H7N5O6
CAS号:
分子量:
305.20
Beilstein:
1555224
MDL编号:
UNSPSC代码:
12352106
PubChem化学物质编号:

方案

≥95%

表单

powder

反应适用性

reagent type: cross-linking reagent

颜色

yellow to yellow-orange

溶解性

ethyl acetate: 25 mg/mL
DMF: soluble

官能团

NHS ester

储存温度

2-8°C

SMILES字符串

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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应用

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.

注意

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.

其他说明

需要注意的是,相比简单的芳基叠氮化合物,硝基取代基提供的吸收谱带波长更长。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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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