{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T07:05:15Z","timestamp":1762067115907},"reference-count":31,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2004,9,21]],"date-time":"2004-09-21T00:00:00Z","timestamp":1095724800000},"content-version":"vor","delay-in-days":5377,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[1990,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The inversion from R\u2010 to S\u2010enantiomer that occurs for some arylpropionic acids may have both toxicological and therapeutic implications. To characterize some properties of this inversion, arylpropionyl\u2010CoA thioester formation was studied in rat tissue homogenates and subcellular fractions for the enantiomers of fenoprofen, ibuprofen, and flurbiprofen. Thioesters were formed from (R)\u2010fenoprofen (64%) and (R)\u2010ibuprofen (33%) but not from the corresponding S\u2010enantiomers or the enantiomers of flurbiprofen. This correlates with the extensive inversion of fenoprofen and ibuprofen and lack of inversion of flurbiprofen in vivo. Subcellular fractions from rat liver showed thioester formation to occur in mitochondria and microsomes but not cytosol. Once formed, the thioesters were readily racemized by whole rat liver homogenate, mitochondria, and cytosol, but only partially inverted (S:R = 0.3) in microsomes. Thioester formation from fenoprofen and ibuprofen was studied in tissue homogenate obtained from liver, diaphragm, kidney, lung, skeletal muscle, smooth muscle, fat, caecum, and intestines. The liver was at least 50\u2010fold more efficient than the other tissues studied and would be expected to be a major organ of enantiomeric inversion. Our data support the hypothesis that R\u2010 to S\u2010enantiomeric inversion of arylpropionic acids proceeds via the stereoselective formation of CoA thioesters followed by enzymatic racemization and hydrolysis of the thioesters to regenerate free acid.<\/jats:p>","DOI":"10.1002\/chir.530020202","type":"journal-article","created":{"date-parts":[[2005,1,7]],"date-time":"2005-01-07T06:15:59Z","timestamp":1105078559000},"page":"67-73","source":"Crossref","is-referenced-by-count":54,"title":["Stereoselective arylpropionyl\u2010CoA thioester formation in vitro"],"prefix":"10.1002","volume":"2","author":[{"given":"M. P.","family":"Knadler","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"S. D.","family":"Hall","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2004,9,21]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600770805"},{"key":"e_1_2_1_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(74)90231-9"},{"key":"e_1_2_1_4_2","doi-asserted-by":"publisher","DOI":"10.1248\/bpb1978.4.1"},{"key":"e_1_2_1_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(88)90762-9"},{"key":"e_1_2_1_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(86)90443-0"},{"key":"e_1_2_1_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(88)90537-0"},{"key":"e_1_2_1_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(83)90107-7"},{"key":"e_1_2_1_9_2","first-page":"94","volume-title":"Methods of Enzymology","author":"Johnson D.","year":"1967"},{"key":"e_1_2_1_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(85)90442-7"},{"key":"e_1_2_1_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2760(87)90088-9"},{"key":"e_1_2_1_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(87)90625-3"},{"key":"e_1_2_1_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2760(87)90006-3"},{"key":"e_1_2_1_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196203511"},{"key":"e_1_2_1_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-4347(00)82666-3"},{"key":"e_1_2_1_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(88)90382-6"},{"key":"e_1_2_1_17_2","first-page":"1704","article-title":"Specificity of long chain acyl coenzyme\u2010A synthetase from rat liver microsomes","volume":"11","author":"Suzue G.","year":"1972","journal-title":"Influences of the position of double bonds in octadecadienoic acid. Biochemistry"},{"key":"e_1_2_1_18_2","volume-title":"Biometry","author":"Sokal R.R.","year":"1981"},{"key":"e_1_2_1_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2760(71)90253-0"},{"key":"e_1_2_1_20_2","doi-asserted-by":"crossref","first-page":"3065","DOI":"10.1016\/S0021-9258(18)50121-6","article-title":"Metabolism of propionic acid in animal tissues","volume":"237","author":"Mazumder R.","year":"1962","journal-title":"J. Biol. Chem."},{"key":"e_1_2_1_21_2","first-page":"283","volume-title":"Advances in Enzymology","author":"Kaziro Y.","year":"1964"},{"key":"e_1_2_1_22_2","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0022-2275(20)41570-6","article-title":"The participation of ethyl 4\u2010benzyloxybenzoate (BRL10894) and other aryl\u2010substituted acids in glycerolipid metabolism","volume":"19","author":"Fears R.","year":"1987","journal-title":"J. Lipid Res."},{"key":"e_1_2_1_23_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2125.1985.tb02694.x"},{"key":"e_1_2_1_24_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF03189920"},{"key":"e_1_2_1_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600740122"},{"key":"e_1_2_1_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1874-6047(08)60146-8"},{"key":"e_1_2_1_27_2","first-page":"517","article-title":"Mechanistic studies of the metabolic chiral inversion of (R)\u2010ibuprofen in humans","volume":"249","author":"Baillie T.A.","year":"1989","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"e_1_2_1_28_2","doi-asserted-by":"publisher","DOI":"10.3109\/00498258809041690"},{"key":"e_1_2_1_29_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF03189461"},{"key":"e_1_2_1_30_2","first-page":"529","article-title":"Stereoselective metabolism of 2\u2010phenylpropionic acid in rat: 1. In vitro studies on the stereoselective isomerization and glucuronidation of 2\u2010phenylpropionic acid","volume":"15","author":"Nakamura Y.","year":"1987","journal-title":"Drug. Metab. Dispos."},{"key":"e_1_2_1_31_2","first-page":"636","article-title":"Ibuprofen stereoisomer heaptic clearance and distribution in normal and fatty in situ perfused rat liver","volume":"232","author":"Cox J.W.","year":"1985","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"e_1_2_1_32_2","doi-asserted-by":"publisher","DOI":"10.1023\/A:1015979915771"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.530020202","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.530020202","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,22]],"date-time":"2023-10-22T07:20:10Z","timestamp":1697959210000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.530020202"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1990,1]]},"references-count":31,"journal-issue":{"issue":"2","published-print":{"date-parts":[[1990,1]]}},"alternative-id":["10.1002\/chir.530020202"],"URL":"https:\/\/doi.org\/10.1002\/chir.530020202","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[1990,1]]}}}