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A3282

Sigma-Aldrich

5-Azido-2-nitrobenzoesäure-N-hydroxysuccinimid-Ester

≥95%, powder

Synonym(e):

N-(5-Azido-2-nitrobenzoyloxy)-succinimid, N-Succinimidyl-5-azido-2-nitro-benzoat

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About This Item

Empirische Formel (Hill-System):
C11H7N5O6
CAS-Nummer:
60117-35-3
Molekulargewicht:
305.20
Beilstein:
1555224
MDL-Nummer:
MFCD00054962
UNSPSC-Code:
12352106
PubChem Substanz-ID:
329770717

Assay

≥95%

Form

powder

Eignung der Reaktion

reagent type: cross-linking reagent

Farbe

yellow to yellow-orange

Löslichkeit

ethyl acetate: 25 mg/mL
DMF: soluble

Funktionelle Gruppe

NHS ester

Lagertemp.

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

InChIKey

FUOJEDZPVVDXHI-UHFFFAOYSA-N

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Anwendung

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.

Vorsicht

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.

Sonstige Hinweise

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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O W Nadeau et al.
Biochemistry, 38(8), 2551-2559 (1999-02-25)
Phosphorylase kinase, a regulatory enzyme of glycogenolysis in skeletal muscle, is a hexadecameric oligomer consisting of four copies each of a catalytic subunit (gamma) and three regulatory subunits (alpha, beta, and delta, the last being endogenous calmodulin). The enzyme is
P Wang et al.
Journal of immunology (Baltimore, Md. : 1950), 157(1), 213-220 (1996-07-01)
Cytotoxic T lymphocytes recognize antigenic peptides presented by MHC class I molecules. The peptides are generated in the cytosol by proteasomes, and probably also other proteases, and are then translocated into the endoplasmic reticulum (ER) lumen. The transporters associated with
S P Sheikh et al.
The Journal of biological chemistry, 265(14), 8304-8310 (1990-05-15)
Pharmacological studies indicate that peptide YY (PYY) and neuropeptide Y interact with multiple binding sites, categorized as Y1 and Y2 subtypes. In order to identify and structurally characterize the Y1 and Y2 receptors we covalently cross-linked [125I-Tyr36]PYY to its receptors.
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 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
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