Linked Life Data

7320628

Source:http://linkedlifedata.com/resource/pubmed/id/7320628

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
8
pubmed:dateCreated
1982-3-13
pubmed:abstractText
(22R and 22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acids were synthesized, starting from chenodeoxycholic acid, in order to establish the chemical structure of haemulcholic acid, which has been found in certain fish as the major bile component. Oxidative decarboxylation of diformoxylated chenodeoxycholic acid with lead tetraacetate yielded 24-nor-5 beta-chol-22-ene-3 alpha, 7 alpha-diol, which was hydroxylated to form a mixture of (22R and 22S)-24-nor-5 beta-cholane-3 alpha, 7 alpha, 22,23-tetrols. Lead tetraacetate oxidation of the mixture yielded 3 alpha, 7 alpha-dihydroxy-23,24-dinor-5 beta-cholan-22-a1. A Reformatsky reaction of the dihydroxydinorcholanal with bromoacetate resulted in the formation of a mixture of (22R and 22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acids. The bile acids epimeric at C-22 were resolved by silica gel column chromatography, and their configurations of C-22 were assigned by a modification of Horeau's method and 13C-nuclear magnetic resonance spectroscopy. By direct comparison with synthetic bile acids, the naturally occurring haemulcholic acid was shown to be (22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acid.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Nov
pubmed:issn
0022-2275
pubmed:author
pubmed:issnType
Print
pubmed:volume
22
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1181-7
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
1981
pubmed:articleTitle
Synthesis of (22R and 22S)-3 alpha, 7 alpha, 22-trihydroxy-5 beta-cholan-24-oic acids and structure of haemulcholic acid, a unique bile acid isolated from fish bile.
pubmed:publicationType
Journal Article