Bile, acid structure

K. Miki, A. Masui, N. Kasai, M. Miyata, M. Shibakami, K. Takemoto, New Channel-Type Inclusion Compound of Steroidal Bile Acid Structure of a 1 1 Complex between Cholic Acid and Acetophenone , J. Am. Chem. Soc., 110, 6594 (1988)... 

Miki, K., Masui, A., Kasai, N., Miyata, M., Shibakami, M., and Takemoto, K., New channel-type inclusion compound of steroidal bile acid. Structure of a 1 1 complex between cholic acid and acetophenone, J.Am. Chem. Soc. 110, 6594-6596 (1988). 

The rate of hydrolysis may vary with the bile acid structure. The hindered nature of the peptide bond in the taurine-conjugated 3 ,7a, l2a-trihydroxy-5 3-cholestanoic acid may explain why this conjugate is more resistant to saponification than C24 acids (59). 

Roda, A., Minutello, A., Angellotti, M., and Fini, A. 1990, Bile acid structure-activity relationship Evaluation of bile acid lipophilicity using 1-octanol/water partition coefficient and reverse phase HPLC. J. Lipid Res. 31, 1433. 

Steroids are another class of natural products with multiple chirality centers One such compound is cholic acid which can be obtained from bile Its structural formula IS given m Figure 7 12 Cholic acid has 11 chirality centers and so a total (including cholic acid) of 2" or 2048 stereoisomers have this constitution Of these 2048 stereoiso mers how many are diastereomers of cholic acid s Remember Diastereomers are stereoisomers that are not enantiomers and any object can have only one mirror image Therefore of the 2048 stereoisomers one is cholic acid one is its enantiomer and the other 2046 are diastereomers of cholic acid Only a small fraction of these compounds are known and (+) cholic acid is the only one ever isolated from natural sources... 

The most prevalent steroid in animal cells is cholesterol (Figure 25.30). Plants contain no cholesterol, but they do contain other steroids very similar to cholesterol in structure (see page 256). Cholesterol serves as a crucial component of cell membranes and as a precursor to bile acids (e.g., cholate, glycocholate,... 

Bile Acids. Figure 1 Structure of selected bile acids. 

Figure 7.13 shows some of the structures of common bile acids. In low ionic strength solutions, sodium taurocholate forms tetrameric aggregates, with critical... 

Fujino, T., Une, M., Imanaka, T., Inoue, K. and Nishimaki-Mogami, T. (2004) Structure-activity relationship of bile acids and bile acid analogs in regard to FXR activation. Journal of Lipid Research, 45, 132-138. 

Pellicciari, R., Costantino, G., Camaioni, E., Sadeghpour, B.M., Entrena, A., Willson, T.M., Fiorucci, S., Clerici, C. and Gioielli, A. (2004) Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure-activity relationship of a series of body and... 

The aggregation behavior of C21-DA salt in dilute electrolyte medium appears to resemble that of certain polyhydroxy bile salts (25,16). That C21-DA, with a structure quite different from bile acids, should possess solution properties similar to, e.g., cholic acid is not entirely surprising in light of recent conductivity and surface tension measurements on purified (i.e., essentially monocarboxylate free) disodium salt aqueous solutions, and of film balance studies on acidic substrates (IX) The data in Figure 3 suggest that C21-DA salt micelles Incorporate detergents - up to an approximate weight fraction of 0.5 -much like cholate Incorporates lecithin or soluble... 

Shortly after his thesis work was accepted, Deulofeu proceeded to the University of Munich, where he worked under Prof. H. Wieland on the structural elucidation of bile acids, a subject that had earned Prof. Wieland the 1927 Nobel prize for Chemistry. Deulofeu s stay in Germany was interrupted by a call from Prof. B. Houssay, who offered him a position as Assistant Professor of Biological Chemistry at the Facultad de Medicina of the Universidad of Buenos Aires, a position that he held until 1948 as a part-time professor. 

Figure 1.2 Structure of a mixed bile-acid/fatty-acid micelle, whereby the hydrophilic (OH groups of BA) are radially arranged on the outside of the micelle and the hydrophobic moieties are arranged on the interior. As well as a classic micelle, a cylindrical mixed micelle structure is also shown.

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