1214. BIGCHAP

Nomenclature

CAS number: 86303-22-2
(3α,5β,7α,12α)-N,N-Bis[3-(d-gluconoylamino)propyl]-3,7,12-trihydroxycholan-24-amide.
C42H75N3O16; mol wt 878.06.
C 57.45%, H 8.61%, N 4.79%, O 29.15%.

Description and references

Homogeneous nonionic detergent; derivative of cholic acid, q.v. Prepn: L. M. Hjelmeland et al., Anal. Biochem. 130, 485 (1983). QSAR study as surfactant: P. Campbell et al., Biotechnol. Bioeng. 64, 527 (1999). Use in protein purification via hydrophobic interaction displacement chromatography: K. M. Sunasara et al., ibid. 82, 330 (2003). Clinical evaluation as a transduction enhancing agent in gene therapy: J. Kuball et al., J. Clin. Oncol. 20, 957 (2002).

Chemical structure

Properties

Crystals at 0° from 2-propanol. Critical micelle conc: 2.9 mM; also reported as 3.4 mM. Log P (octanol/water): 2.450. Dipole moment: 7.44 D.

Derivative

Deoxy-BIGCHAP.

Nomenclature

CAS number: 86303-23-3
N,N′-[[[(3α,5β,12α)-3,12-Dihydroxy-24-oxocholan-24-yl]imino]di-3,1-propandiyl]bis-d-gluconamide.
C42H75N3O15; mol wt 862.06.
C 58.52%, H 8.77%, N 4.87%, O 27.84%.

Description and references

Use as mobile phase additive in microcolumn LC: W. Hu et al., J. High Resolut. Chromatogr. 15, 275 (1992).

Properties

Critical micelle conc: 1.4 mM.

Use

Surfactant and solubilizer for biological systems.