Synthesis of ester-linked lithocholic acid dimers.
Four lithocholic acid dimers were synthesised via esterification. The ester-linked dimer, 3-oxo-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), was obtained by condensation of methyl lithocholate with 3-oxo-5beta-cholan-24-oic acid. Borohydride reduction of this ester-linked dimer gave 3alpha-hydroxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), which was acetylated to 3alpha-acetoxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta). Reaction of methyl lithocholate with oxalyl chloride yielded the oxalate dimer, bis(5beta-cholan-24-oic acid methyl ester)-3alpha-yl oxalate.
Nahar
Lutfun
L
Japp Laboratory, Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, UK. l.nahar@abdn.ac.uk
Turner
Alan B
AB
D003902:Detergents; D019281:Dimerization; D004951:Esterification; D004952:Esters / Q000737:chemistry* / Q000378:metabolism; D006868:Hydrolysis; D008095:Lithocholic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism
D003902:Detergents; D004952:Esters; D008095:Lithocholic Acid