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2-Iminobiotin
Chemischer Name: 5-((4S)-2-iminohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid // Synonyme: Hexahydro-2-imino-1H-thieno[3,4-d]imidazole-4-pentanoic acid, Guanidinobiotin
- Art-Nr.:LS-4320
- CAS Nr.:13395-35-2
- Formel:C10H17N3O2S
- Molare Masse:243,32 g/mol
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description
In comparison to biotin (Ka = 1015 M-1) and desthiobiotin (Ka = 1011 M-1), the guanidino analog of biotin (= 2-iminobiotin) shows an even weaker binding affinity (Ka = 108 M-1) for avidin, which is, in addition, pH-dependent. At high pH (> 9), iminobiotin-tagged proteins bind to avidin conjugates with high affinity, but the avidin–iminobiotin complexes dissociate at low pH (~ 4) or via replacement upon addition of biotin. This allows the purification of the captured protein without denaturation releasing biologically functional, iminobiotinylated-proteins from the avidin conjugates. Besides, 2-Iminobiotin reversibly inhibits nitric oxide synthases (NOS). NOS oxidizes the guanidino-nitrogen of L-arginine resulting in L-citrulline and nitric oxide.
references
Iminobiotin affinitiy columns and their application to retrieval of streptavidin; K. Hofmann, S. W. Wood, C. C. Brinton, J. A. Montibeller, F. M. Finn; Proc. Natl. Acad. Sci. USA 1980; 77(8): 4666-4668. https://doi.org/10.1073/pnas.77.8.4666.
Voltammetric homogeneous binding assay of biotin without a separation step using iminobiotin labeled with an electroactive compound; K. Sugawara, N. Kamiya, G. Hirabayashi, H. Kuramitz; Anal Sci 2005; 21(8): 897-900. https://doi.org/10.2116/analsci.21.897.
The use of the 2-iminobiotin-avidin interaction for the selective retrieval of labeled plasma membrane components; G. A. Orr; J. Biol. Chem. 1981; 256(2): 761-766.
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