Chemical synthesis of (22E)-3alpha,6alpha,7alpha,12alpha-Tetrahydroxy-5beta-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine: precursors of the [22,23-(3)H] labelled tracers.
(22E)-3alpha,6alpha,7alpha,12alpha-Tetrahydroxy-5beta-chol-22-en-24-oic acid and its N-acylamidated conjugates with glycine or taurine were synthesized from cholic acid. The key reactions employed are: 1) degradation of the side chain in intermediary C(24) 3alpha,6alpha,7alpha,12alpha-tetrahydroxylated bile acid to the corresponding C(22) 23,24-dinor-aldehyde, followed by Wittig reaction with methyl (triphenylphosphoranylidene)acetate and 2) N-acylamidation of the unconjugated tetrahydroxy-Delta(22)-5beta-cholenoic acid with glycine (or taurine) in the presence of diethylphosphorocyanide and triethylamine as coupling reagents.
Ogawa
Shoujiro
S
Department of Chemistry, College of Humanities & Sciences, Nihon University, 3-25-40 Sakurajousui, Setagaya-ku, Tokyo, Japan.
Adachi
Yuuki
Y
Kakiyama
Genta
G
Shimada
Miki
M
Mano
Nariyasu
N
Goto
Junichi
J
Iida
Takashi
T
D000577:Amides / Q000737:chemistry*; D019826:Cholic Acid / Q000737:chemistry; D002793:Cholic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005998:Glycine / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013654:Taurine / Q000737:chemistry*
C554026:(22E)-3alpha,6alpha,7alpha,12alpha-tetrahydroxy-5beta-chol-22-en-24-oic acid; D000577:Amides; D002793:Cholic Acids; D013654:Taurine; D019826:Cholic Acid; D005998:Glycine