{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,4]],"date-time":"2026-06-04T08:56:55Z","timestamp":1780563415459,"version":"3.54.1"},"reference-count":22,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2001,10,15]],"date-time":"2001-10-15T00:00:00Z","timestamp":1003104000000},"content-version":"vor","delay-in-days":44,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J of Molecular Recognition"],"published-print":{"date-parts":[[2001,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>IgE antibodies in the sera of subjects allergic to \u03b2\u2010lactam antibiotics detect a spectrum of specificities ranging from side\u2010chain groups to an entire penicillin or cephalosporin molecule. In addition to such structural heterogeneity of allergenic determinants, IgE antibodies in the sera of different allergic subjects show heterogeneous recognition responses. Detailed immunochemical studies were carried out on the sera of penicillin\u2010allergic subjects that showed selective and unexpected reactions with the frequently prescribed penicillin, amoxicillin. Antibodies from one subject reacted only with the amoxicilloyl determinant while IgE from another subject showed multiple reactivity with penicilloyl and penicillanyl determinants of different penicillins but not with the amoxicilloyl determinant. Quantitative hapten inhibition studies revealed that the combining sites of the former antibodies were complementary to amoxicillin in a form that permits binding to the hydroxyaminobenzyl side\u2010chain and the thiazolidine ring carboxyl. These conditions are satisfied with the drug in the \u2018\u2010oyl\u2019 but not in the \u2018\u2010anyl\u2019 form which involves linkage through the 2\u2010carboxyl of the thiazolidine ring. With the second serum, adsorption studies showed that the wide\u2010ranging reactivity of IgE was due to a single population of antibodies that detected a common specificity on the different penicillins. Combining site studies revealed clear recognition of the benzyl portion of the side\u2010chain of benzylpenicilloyl, benzylpenicillanyl, ampicilloyl, ampicillanyl and amoxicillanyl determinants when free antibody access to the side\u2010chain was possible but little or no recognition of the ring hydroxyl of amoxicillin. Such uninhibited access may not occur, however, when amoxicillin is conjugated in the \u2018\u2010oyl\u2019 form since opening the \u03b2\u2010lactam ring allows increased flexibility and rotation of the molecule and the possibility of close association of the hydroxyaminobenzyl side\u2010chain of amoxicillin with the linked peptide carrier. In such close steric association, H\u2010bonding involving the ring hydroxyl and amino acids of the carrier may prevent antibody access to the side\u2010chain region of the amoxicilloyl determinant. Copyright \u00a9 2001 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/jmr.541","type":"journal-article","created":{"date-parts":[[2002,8,25]],"date-time":"2002-08-25T16:20:51Z","timestamp":1030292451000},"page":"300-307","source":"Crossref","is-referenced-by-count":13,"title":["Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects"],"prefix":"10.1002","volume":"14","author":[{"given":"Zhenjun","family":"Zhao","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Brian A.","family":"Baldo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karl. W.","family":"Baumgart","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominic F. J.","family":"Mallon","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2001,10,15]]},"reference":[{"key":"e_1_2_1_2_1","doi-asserted-by":"publisher","DOI":"10.1027\/0838-1925.12.5.206"},{"key":"e_1_2_1_3_1","series-title":"Monographs in Allergy","first-page":"11","volume-title":"Molecular Approach to the Study of Allergens","author":"Baldo BA","year":"1990"},{"key":"e_1_2_1_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx00042a001"},{"key":"e_1_2_1_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/jmr.300080302"},{"key":"e_1_2_1_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11882-001-0093-4"},{"key":"e_1_2_1_7_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1398-9995.1988.tb01628.x"},{"key":"e_1_2_1_8_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2222.1990.tb03139.x"},{"key":"e_1_2_1_9_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1398-9995.1995.tb02584.x"},{"key":"e_1_2_1_10_1","series-title":"The Antigens","first-page":"73","author":"Dewdney JM","year":"1977"},{"key":"e_1_2_1_11_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-3-642-69088-4_16"},{"key":"e_1_2_1_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/0161-5890(90)90094-G"},{"key":"e_1_2_1_13_1","doi-asserted-by":"publisher","DOI":"10.1159\/000235177"},{"key":"e_1_2_1_14_1","doi-asserted-by":"publisher","DOI":"10.1056\/NEJM196611172752009"},{"key":"e_1_2_1_15_1","series-title":"Textbook of Immunopathology","first-page":"403","author":"Levine BB","year":"1976"},{"key":"e_1_2_1_16_1","doi-asserted-by":"publisher","DOI":"10.1159\/000230197"},{"key":"e_1_2_1_17_1","series-title":"Clinical Immunology","first-page":"1219","author":"Parker CW","year":"1980"},{"key":"e_1_2_1_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1352(199607)9:4<287::AID-JMR340>3.0.CO;2-L"},{"key":"e_1_2_1_19_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2222.1996.tb00502.x"},{"key":"e_1_2_1_20_1","doi-asserted-by":"publisher","DOI":"10.1081\/IAS-100102897"},{"key":"e_1_2_1_21_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2222.2000.00887.x"},{"key":"e_1_2_1_22_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2222.1988.tb02904.x"},{"key":"e_1_2_1_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1759(00)00213-1"}],"container-title":["Journal of Molecular Recognition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjmr.541","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jmr.541","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,11,19]],"date-time":"2023-11-19T15:09:53Z","timestamp":1700406593000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/jmr.541"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2001,9]]},"references-count":22,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2001,9]]}},"alternative-id":["10.1002\/jmr.541"],"URL":"https:\/\/doi.org\/10.1002\/jmr.541","archive":["Portico"],"relation":{},"ISSN":["0952-3499","1099-1352"],"issn-type":[{"value":"0952-3499","type":"print"},{"value":"1099-1352","type":"electronic"}],"subject":[],"published":{"date-parts":[[2001,9]]}}}