{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T00:42:35Z","timestamp":1761007355218,"version":"build-2065373602"},"reference-count":41,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[1998,3,1]],"date-time":"1998-03-01T00:00:00Z","timestamp":888710400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Lipids"],"published-print":{"date-parts":[[1998,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In recent years, defects of bile acid synthesis caused by disorders of peroxisome biogenesis have led to increased interest in C<jats:sub>27<\/jats:sub> bile acids. In humans, while the majority of bile acids are C<jats:sub>24<\/jats:sub> carboxylic acids, the presence of increased concentrations of C<jats:sub>27<\/jats:sub> bile acids and their metabolites in hereditary diseases associated with peroxisomal dysfunction can serve as a useful marker for the intensity of the metabolic disorder. Our present studies describe an efficient method for the rapid hydrolysis of C<jats:sub>27<\/jats:sub> and C<jats:sub>24<\/jats:sub> bile acid conjugates using a commercial microwave oven. The advantages of this method include freedom from racemization, minimal activation, mild reaction conditions, and the highly stereocontrolled nature of the reaction, thus allowing for free bile acid recovery in high yield. For example, when (25<jats:italic>R<\/jats:italic>) 3\u03b1,7\u03b1,12\u03b1\u2010trihydroxy\u20105\u03b2\u2010cholestan\u201026\u2010oyl taurine, a major compound present in the bile of <jats:italic>Alligator mississippiensis<\/jats:italic>, was deconjugated with 4% NaOH\/diethylene glycol or 1 M LiOH\/propylene glycol in the microwave oven for 4\u20136 min, 3\u03b1,7\u03b1,12\u03b1\u2010trihydroxy\u20105\u03b2\u2010cholestan\u201026\u2010oic acid (THCA) was obtained in 81% yield with retention of configuration at C\u201025. It is suggested that present studies will be helpful in delineating the absolute stereochemistry of 3\u03b1,7\u03b1,12\u03b1\u2010trihydroxy\u20105\u03b2\u2010cholestanoyl\u2010CoA oxidase, the peroxisomal enzyme that catalyzes the first step in the oxidation of THCA.<\/jats:p>","DOI":"10.1007\/s11745-998-0213-y","type":"journal-article","created":{"date-parts":[[2006,11,13]],"date-time":"2006-11-13T13:18:47Z","timestamp":1163423927000},"page":"333-338","source":"Crossref","is-referenced-by-count":10,"title":["Rapid hydrolysis of bile acid conjugates using microwaves: Retention of absolute stereochemistry in the hydrolysis of (25<i>R<\/i>) 3\u03b1,7\u03b1,12\u03b1\u2010trihydroxy\u20105\u03b2\u2010cholestan\u201026\u2010oyltaurine"],"prefix":"10.1002","volume":"33","author":[{"given":"Bishambar","family":"Dayal","sequence":"first","affiliation":[{"name":"Medical Service Department of Veterans Affairs Medical Center East Orange New Jersey 07018"},{"name":"Department of Medicine UMDNJ\u2010New Jersey Medical School Newark New Jersey 07103"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Norman H.","family":"Ertel","sequence":"additional","affiliation":[{"name":"Medical Service Department of Veterans Affairs Medical Center East Orange New Jersey 07018"},{"name":"Robert Wood Johnson Medical School New Brunswick New Jersey"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[1998,3]]},"reference":[{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/jcp.1041510115"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.1546315"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/ng0492-16"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00444751"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.424737"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0300-5089(21)00383-7"},{"key":"e_1_2_2_8_1","first-page":"429","volume-title":"The Liver","author":"Carey M.C.","year":"1982"},{"key":"e_1_2_2_9_1","first-page":"189","volume-title":"Biochemistry of Cholesterol","author":"Gibbons G.F.","year":"1982"},{"volume-title":"The Biological Importance of Bile Salts","year":"1978","author":"Haslewood G.A.D.","key":"e_1_2_2_10_1"},{"key":"e_1_2_2_11_1","first-page":"16","volume-title":"Bile Salts","author":"Haslewood G.A.D.","year":"1967"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)96311-8"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2275(20)38791-5"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(17)42510-5"},{"key":"e_1_2_2_15_1","first-page":"245","volume-title":"Advances in Glucuronide Conjugation","author":"Hofmann A.F.","year":"1985"},{"key":"e_1_2_2_16_1","first-page":"1425","article-title":"Pancreatic Carboxypeptidase Hydrolysis of Bile Acid\u2010\u2010Amino Acid Conjugates: Selective Resistance of Glycine and Taurine Amidates","volume":"88","author":"Huijghebaert S.","year":"1985","journal-title":"Gastroenterology"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)86403-7"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2275(20)39844-8"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-3084(91)90068-M"},{"key":"e_1_2_2_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0039-128X(84)80018-5"},{"key":"e_1_2_2_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/0039-128X(84)90030-8"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/0039-128X(95)00004-A"},{"key":"e_1_2_2_23_1","doi-asserted-by":"crossref","unstructured":"Dayal B. Rapole K.R. Wilson S.R. Shefer S. Tint G.S. andSalen G.(1995)Microwave\u2010Induced Rapid Synthesis of Bile Acid Conjugates Synlett (No. 8) 861\u2013862.","DOI":"10.1055\/s-1995-5101"},{"key":"e_1_2_2_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/0960-894X(95)00211-B"},{"key":"e_1_2_2_25_1","unstructured":"Dayal B. Ertel N.H. Kothavali M. Kristol D. Asgaonkar A. Pramanik B.N. Bartner P. andSalen G.(1996)Microwave\u2010Mediated Stereoselective Synthesis of 3\u2010Ketocholesterol and Cholesterol Ester Epoxides Eastern Anal. Symposium Nov. 17\u2010\u201022 Somerset NJ (abstract 361)."},{"key":"e_1_2_2_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0039-128X(97)00010-X"},{"key":"e_1_2_2_27_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac199466102037"},{"key":"e_1_2_2_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0039-128X(97)00007-X"},{"key":"e_1_2_2_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2275(20)39994-6"},{"key":"e_1_2_2_30_1","doi-asserted-by":"publisher","DOI":"10.3987\/COM-96-S37"},{"key":"e_1_2_2_31_1","first-page":"18","article-title":"MORE Chemistry in a Microwave","volume":"27","author":"Bose A.K.","year":"1997","journal-title":"Chemtech"},{"key":"e_1_2_2_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(94)02225-Z"},{"key":"e_1_2_2_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)01571-7"},{"key":"e_1_2_2_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(95)00662-R"},{"key":"e_1_2_2_35_1","doi-asserted-by":"publisher","DOI":"10.1080\/00304949109458244"},{"key":"e_1_2_2_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)01520-7"},{"key":"e_1_2_2_37_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397919308012590"},{"volume-title":"An Evaluation of Microwave Heating for the Vapor Phase Hydrolysis of Proteins","year":"1989","author":"Gilman L.B.","key":"e_1_2_2_38_1"},{"key":"e_1_2_2_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00253a047"},{"key":"e_1_2_2_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2275(20)38464-9"},{"key":"e_1_2_2_41_1","doi-asserted-by":"crossref","unstructured":"Pedersen J.I. Veggan T. andBjorkhem I.(1996)Substrate Stereospecificity in Oxidation of (25S)\u20103\u03b1 7\u03b1 12\u03b1\u2010Trihydroxy\u20105\u03b2\u2010cholestanoyl\u2010CoA by Peroxisomal Trihydroxy\u20105\u03b2\u2010cholestanoyl\u2010CoA Oxidase in Bile Acids in Hepatobiliary Diseases: Basic Research and Clinical Application Proceedings of the Falk in SymposiumNo. 93 XIV International Bile Acid Meeting (Paumgartner G. Stiehl A. andGerok W. eds.) Freiburg Germany October 22\u2010\u201024 (abstract 14).","DOI":"10.1006\/bbrc.1996.0981"},{"key":"e_1_2_2_42_1","unstructured":"Setchell K.D.R. Heubi J.E. O'Connell N.C. HofmannA.F. andLavine J.E.(1996)Identification of a Unique Inborn Error in Bile Acid Conjugation Involving a Deficiency in Amidation inProceedings of the Falk Symposium No. 93 XIV International Bile Acid Meeting (Paumgartner G. Stiehl A. andGerok W. eds.) held in Freiburg Germany October 22\u2010\u201024 (abstract pp.9\u201310)."}],"container-title":["Lipids"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/pdf\/10.1007\/s11745-998-0213-y","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T13:01:43Z","timestamp":1760965303000},"score":1,"resource":{"primary":{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/10.1007\/s11745-998-0213-y"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1998,3]]},"references-count":41,"journal-issue":{"issue":"3","published-print":{"date-parts":[[1998,3]]}},"alternative-id":["10.1007\/s11745-998-0213-y"],"URL":"https:\/\/doi.org\/10.1007\/s11745-998-0213-y","archive":["Portico"],"relation":{},"ISSN":["0024-4201","1558-9307"],"issn-type":[{"type":"print","value":"0024-4201"},{"type":"electronic","value":"1558-9307"}],"subject":[],"published":{"date-parts":[[1998,3]]}}}