Antimicrobial activity of basic cholane derivatives. X. Synthesis of 3 alpha- and 3 beta-amino-5 beta-cholan-24-oic acids.
A simple and convenient route to 3 alpha- and 3 beta-amino-5 beta-cholan-24-oic acids was developed via Leuckart-Wallach amination reduction and subsequent acid hydrolysis. Two epimeric formylamino derivatives were produced (alpha and beta), approximately in a 1:1 ratio, as determined by 13C nuclear magnetic resonance spectroscopy. The two isomers were separated by making use of their different solubilities in ethyl ether. The absolute configuration of the two amino acids was assigned by comparison with authentic reference samples.
Bellini
A M
AM
Dipartimento di Scienze Farmaceutiche, Ferrara, Italy.
Mencini
E
E
Quaglio
M P
MP
Guarneri
M
M
Fini
A
A
D008095:Lithocholic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C072603:3-aminocholan-24-oic acid; D008095:Lithocholic Acid