| Nuclear magnetic resonance spectroscopy of bile acids. Development of two-dimensional NMR methods for the elucidation of proton resonance assignments for five common hydroxylated bile acids, and their parent bile acid, 5 beta-cholanoic acid. | |
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MedLine Citation:
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PMID: 4067429 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The complete 1H nuclear magnetic resonance assignments have been made for the common mono-, di-, and trihydroxy 5 beta-cholanoic acids; lithocholic acid, chenodeoxycholic acid, ursodeoxycholic acid, deoxycholic acid, cholic acid, and the unsubstituted parent compound, 5 beta-cholanoic acid, by heteronuclear-correlated two-dimensional NMR. The known 13C chemical shifts of these compounds were used to make the proton resonance assignments, and consistency of the carbon and proton assignments was verified by expected changes due to substituent effects. This has led to clarification of previously published 13C NMR resonance assignments. Addition of the 3 alpha, 7 alpha, and 12 alpha hydroxyl substituent effects derived from the mono- and dihydroxycholanoic acids yielded predicted values for proton chemical shifts of the trihydroxy-substituted 5 beta-cholanoic acid, cholic acid, that agreed well with experimental values. It is suggested that the individual substituent effects can be used to predict proton chemical shifts for hydroxycholanic acids containing other combinations of 3 alpha, 7 alpha, 7 beta, and 12 alpha hydroxyl groups. |
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Authors:
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D V Waterhous; S Barnes; D D Muccio |
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Publication Detail:
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Type: Journal Article; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Journal of lipid research Volume: 26 ISSN: 0022-2275 ISO Abbreviation: J. Lipid Res. Publication Date: 1985 Sep |
Date Detail:
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Created Date: 1986-01-08 Completed Date: 1986-01-08 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 0376606 Medline TA: J Lipid Res Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 1068-78 Citation Subset: IM |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Bile Acids and Salts
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analysis* Chenodeoxycholic Acid / analysis Cholanes / analysis Cholic Acid Cholic Acids / analysis Deoxycholic Acid / analysis Lithocholic Acid / analysis Magnetic Resonance Spectroscopy / methods Structure-Activity Relationship Ursodeoxycholic Acid / analysis |
| Grant Support | |
ID/Acronym/Agency:
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AM-25511/AM/NIADDK NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Bile Acids and Salts; 0/Cholanes; 0/Cholic Acids; 128-13-2/Ursodeoxycholic Acid; 25312-65-6/cholanic acid; 434-13-9/Lithocholic Acid; 474-25-9/Chenodeoxycholic Acid; 81-25-4/Cholic Acid; 83-44-3/Deoxycholic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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