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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Crosslinking of tropomyosin to myosin subfragment-1 in reconstituted rabbit skeletal thin filaments.
T Tao et al.
FEBS letters, 168(1), 169-173 (1984-03-12)
Rabbit skeletal tropomyosin was labeled with the bifunctional photoactivatable crosslinker N-succinimidyl-6- (4'-azido-2'-nitrophenylamino)hexanoate. After irradiating the rigor complex composed of myosin subfragment-1, crosslinker-labeled tropomyosin, and F-actin, a crosslinked product was formed. This product was identified as a 1:1 adduct of tropomyosin
D S Schalch et al.
Endocrinology, 118(4), 1590-1597 (1986-04-01)
We have characterized the interaction of insulin-like growth factor I/somatomedin C (IGF-I/Sm-C) with its plasma membrane receptors on cultured rat chondrocytes. Our studies have demonstrated that [125I]IGF-I/Sm-C binding to these receptors is a relatively specific, reversible, and time-, temperature-, pH-
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