{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,7,30]],"date-time":"2025-07-30T09:43:25Z","timestamp":1753868605783,"version":"3.41.2"},"reference-count":27,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2024,11,12]],"date-time":"2024-11-12T00:00:00Z","timestamp":1731369600000},"content-version":"vor","delay-in-days":11,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2024,11]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>Olean is the chiral spiroacetal sex pheromone of the female olive fruit fly <jats:italic><jats:styled-content style=\"fixed-case\">Bactrocera oleae<\/jats:styled-content><\/jats:italic>. Laboratory tests have demonstrated that the (<jats:italic>R<\/jats:italic>)\u2010(\u2212)\u2010olean enantiomer is active on males, whereas females respond to (<jats:italic>S<\/jats:italic>)\u2010(+)\u2010olean. Here we present the first HPLC enantioseparation of olean using polysaccharide derivatives as chiral stationary phases and a polarimetric detector equipped with a micro\u2010flow cell capable of detecting optical rotation at six different wavelengths. Unlike blind UV detection, the polarimetric detector allows the chiral spiroacetal, which lacks a chromophore, to be detected as bisegnate peaks, indicating the opposite sign of the optical rotation. The HPLC enantioseparation was optimized on the coated type amylose\u2010based Chiralpak AS\u2010H CSP using a mobile phase consisting of <jats:italic>n<\/jats:italic>\u2010hexane\u20102\u2010propanol 99.99:0.01 (v\/v). These conditions were scaled up to a semi\u2010preparative level and allowed resolution of 2.5\u2009mg of racemic sample in 5\u2009min. Multiwavelength optical rotation detection during HPLC enantioseparation of racemic samples provides a direct readout of the stereochemistry of olean and allows tracking of virtual optical rotation dispersion curves without the need for preliminary collection of enantiomeric samples by semi\u2010preparative HPLC.<\/jats:p>","DOI":"10.1002\/chir.70006","type":"journal-article","created":{"date-parts":[[2024,11,13]],"date-time":"2024-11-13T00:43:25Z","timestamp":1731458605000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Multiwavelength Optical Rotation Detection: An Effective Approach for the Recognition of Analytical and Semi\u2010Preparative HPLC Enantioseparation of the Chiral Pheromone Olean and Its Stereochemical Characterization"],"prefix":"10.1002","volume":"36","author":[{"given":"Francesca\u00a0Romana","family":"Mammone","sequence":"first","affiliation":[{"name":"Centre for the Control and Evaluation of Medicines Istituto Superiore di Sanit\u00e0  Rome Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0808-7644","authenticated-orcid":false,"given":"Daniele","family":"Sadutto","sequence":"additional","affiliation":[{"name":"Centre for the Control and Evaluation of Medicines Istituto Superiore di Sanit\u00e0  Rome Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6346-1953","authenticated-orcid":false,"given":"Roberto","family":"Cirilli","sequence":"additional","affiliation":[{"name":"Centre for the Control and Evaluation of Medicines Istituto Superiore di Sanit\u00e0  Rome Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,11,12]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.08.040"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1584\/jpestics.D22-062"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.2183\/pjab.90.373"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01012372"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00372925"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00365885"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.3390\/insects12121085"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)91192-X"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00024-7"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac199466101991"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/a606625i"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1999-3467"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature10932"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2009.10.022"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.530040306"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20298"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20405"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00330a057"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trac.2019.115709"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules26061747"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules29122895"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules27238527"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10145"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1366\/11-06321"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2010.01.047"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.23668"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20557"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.70006","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,11,15]],"date-time":"2024-11-15T10:04:44Z","timestamp":1731665084000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.70006"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11]]},"references-count":27,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2024,11]]}},"alternative-id":["10.1002\/chir.70006"],"URL":"https:\/\/doi.org\/10.1002\/chir.70006","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"type":"print","value":"0899-0042"},{"type":"electronic","value":"1520-636X"}],"subject":[],"published":{"date-parts":[[2024,11]]},"assertion":[{"value":"2024-08-29","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication 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