rdf:type |
|
lifeskim:mentions |
|
pubmed:issue |
11
|
pubmed:dateCreated |
1992-12-24
|
pubmed:abstractText |
3-N-Acetylglucosaminides of unconjugated, glycine- and taurine-conjugated bile acids have been synthesized. Bile acids appropriately protected were condensed with acetochloroglucosamine through the 3 alpha-hydroxyl group by means of the Koenigs-Knorr reaction using cadmium carbonate as a catalyst. Subsequent borohydride reduction and/or alkaline hydrolysis provided desired 3-N-acetylglucosaminides of unconjugated bile acids. Glycine-conjugates were obtained from N-acetylglucosaminides of unconjugated bile acids and ethyl glycinate by the carbodiimide method. The preparation of N-acetylglucosaminides of taurine-conjugates was attained by the Koenigs-Knorr reaction of bile acid p-nitrophenyl esters followed by condensation with taurine. 7-N-Acetylglucosaminides of ursodeoxycholates were prepared in a similar fashion. The convenient synthesis of 3-N-acetylglucosaminides of unconjugated bile acids is also described.
|
pubmed:language |
eng
|
pubmed:journal |
|
pubmed:citationSubset |
IM
|
pubmed:chemical |
|
pubmed:status |
MEDLINE
|
pubmed:month |
Nov
|
pubmed:issn |
0039-128X
|
pubmed:author |
|
pubmed:issnType |
Print
|
pubmed:volume |
57
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
522-9
|
pubmed:dateRevised |
2006-11-15
|
pubmed:meshHeading |
pubmed-meshheading:1448811-Acetylglucosamine,
pubmed-meshheading:1448811-Bile Acids and Salts,
pubmed-meshheading:1448811-Borohydrides,
pubmed-meshheading:1448811-Cadmium,
pubmed-meshheading:1448811-Carbonates,
pubmed-meshheading:1448811-Catalysis,
pubmed-meshheading:1448811-Glycine,
pubmed-meshheading:1448811-Hydrogen-Ion Concentration,
pubmed-meshheading:1448811-Hydrolysis,
pubmed-meshheading:1448811-Taurine,
pubmed-meshheading:1448811-Ursodeoxycholic Acid
|
pubmed:year |
1992
|
pubmed:articleTitle |
Synthesis of N-acetylglucosaminides of unconjugated and conjugated bile acids.
|
pubmed:affiliation |
Pharmaceutical Institute, Tohoku University, Sendai, Japan.
|
pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
|