A3407
6-(4-Azido-2-nitrophenylamino)hexanoic acid N-hydroxysuccinimide ester
≥85%, powder
Synonym(s):
N-Succinimidyl 6-(4-azido-2-nitroanilino)hexanoate
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About This Item
Empirical Formula (Hill Notation):
C16H18N6O6
CAS Number:
Molecular Weight:
390.35
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
assay
≥85%
form
powder
color
orange
solubility
ethyl acetate: 10 mg/mL, DMF: soluble
storage temp.
−20°C
SMILES string
[O-][N+](=O)c1cc(ccc1NCCCCCC(=O)ON2C(=O)CCC2=O)N=[N+]=[N-]
Application
Photoactive, heterobifunctional cross-linking reagent incorporating an extended spacer. 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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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E Prossnitz et al.
The Journal of biological chemistry, 263(34), 17917-17920 (1988-12-05)
The histidine permease of Salmonella typhimurium consists of four protein components, one located in the periplasm and three in the cytoplasmic membrane. Genetic evidence indicated that the periplasmic protein interacts with the membrane proteins during transport. We have utilized two
J B Monahan et al.
The Journal of biological chemistry, 258(8), 5056-5062 (1983-04-25)
The association of the eighth (C8) and ninth (C9) components of human complement within membrane-bound C5b-9 was investigated using the photosensitive cross-linking reagent N-succinimidyl-6-(4'-azido-2'-nitrophenylamino)hexanoate. Reaction of this reagent with either the purified alpha-gamma or beta subunit of C8 resulted in
G A Marguerie et al.
European journal of biochemistry, 139(1), 5-11 (1984-02-15)
Fibrinogen participates in platelet aggregation via specific inducible receptors on the cell surface. We have used a photoactivable bifunctional reagent, N-succinimidyl-6-(4'-azido-2'-nitrophenylamino)hexanoate, SANAH, to derivatize 125I-labeled-fibrinogen (125I-Fg) and crosslink it to ADP-stimulated platelets. Binding experiments established that 125I-Fg and 125I-Fg-SANAH interacted