| pubmed-article:12227809 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:12227809 | lifeskim:mentions | umls-concept:C0005404 | lld:lifeskim |
| pubmed-article:12227809 | lifeskim:mentions | umls-concept:C1704675 | lld:lifeskim |
| pubmed-article:12227809 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:12227809 | lifeskim:mentions | umls-concept:C0024485 | lld:lifeskim |
| pubmed-article:12227809 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:12227809 | lifeskim:mentions | umls-concept:C0182400 | lld:lifeskim |
| pubmed-article:12227809 | pubmed:issue | 19 | lld:pubmed |
| pubmed-article:12227809 | pubmed:dateCreated | 2002-9-13 | lld:pubmed |
| pubmed-article:12227809 | pubmed:abstractText | Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-(13)C(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-(13)C(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-(13)C(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)-double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-(13)C(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and (1)H-(13)C HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP. | lld:pubmed |
| pubmed-article:12227809 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:grant | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:language | eng | lld:pubmed |
| pubmed-article:12227809 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:12227809 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:12227809 | pubmed:month | Sep | lld:pubmed |
| pubmed-article:12227809 | pubmed:issn | 0022-3263 | lld:pubmed |
| pubmed-article:12227809 | pubmed:author | pubmed-author:TochtropGrego... | lld:pubmed |
| pubmed-article:12227809 | pubmed:author | pubmed-author:DeKosterGrego... | lld:pubmed |
| pubmed-article:12227809 | pubmed:author | pubmed-author:CistolaDavid... | lld:pubmed |
| pubmed-article:12227809 | pubmed:author | pubmed-author:CoveyDouglas... | lld:pubmed |
| pubmed-article:12227809 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:12227809 | pubmed:day | 20 | lld:pubmed |
| pubmed-article:12227809 | pubmed:volume | 67 | lld:pubmed |
| pubmed-article:12227809 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:12227809 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:12227809 | pubmed:pagination | 6764-71 | lld:pubmed |
| pubmed-article:12227809 | pubmed:dateRevised | 2007-11-14 | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
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| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
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| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:meshHeading | pubmed-meshheading:12227809... | lld:pubmed |
| pubmed-article:12227809 | pubmed:year | 2002 | lld:pubmed |
| pubmed-article:12227809 | pubmed:articleTitle | Synthesis of [3,4-(13)c(2)]-enriched bile salts as NMR probes of protein-ligand interactions. | lld:pubmed |
| pubmed-article:12227809 | pubmed:affiliation | Department of Molecular Biology & Pharmacology, Washington University School of Medicine, 660 South Euclid Avenue, Campus Box 8103, St. Louis, Missouri 63110, USA. | lld:pubmed |
| pubmed-article:12227809 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:12227809 | pubmed:publicationType | Research Support, U.S. Gov't, P.H.S. | lld:pubmed |
