{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,29]],"date-time":"2026-06-29T21:12:39Z","timestamp":1782767559481,"version":"3.54.5"},"reference-count":56,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2019,8,19]],"date-time":"2019-08-19T00:00:00Z","timestamp":1566172800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100011019","name":"Nemzeti Kutat\u00e1si Fejleszt\u00e9si \u00e9s Innov\u00e1ci\u00f3s Hivatal","doi-asserted-by":"publisher","award":["K112442"],"award-info":[{"award-number":["K112442"]}],"id":[{"id":"10.13039\/501100011019","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100011019","name":"Nemzeti Kutat\u00e1si Fejleszt\u00e9si \u00e9s Innov\u00e1ci\u00f3s Hivatal","doi-asserted-by":"publisher","award":["K115731"],"award-info":[{"award-number":["K115731"]}],"id":[{"id":"10.13039\/501100011019","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Economic Development and Innovation Operational Programme","award":["GINOP-2.3.2-15-2016-00012"],"award-info":[{"award-number":["GINOP-2.3.2-15-2016-00012"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>A library of isopulegol-based bi-, tri- and tetrafunctional chiral ligands has been developed from commercially available (\u2212)-isopulegol and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. Michael addition of primary amines towards \u03b1-methylene-\u03b3-butyrolactone, followed by reduction, was accomplished to provide aminodiols in highly stereoselective transformations. Stereoselective epoxidation of (+)-neoisopulegol, derived from natural (\u2212)-isopulegol, and subsequent oxirane ring opening with primary amines afforded aminodiols. The regioselective ring closure of N-substituted aminodiols with formaldehyde was also investigated. Hydroxylation of (+)-neoisopulegol resulted in diol, which was then transformed into aminotriols by aminolysis of its epoxides. Dihydroxylation of (+)-neoisopulegol or derivatives with OsO4\/NMO gave neoisopulegol-based di-, tri- and tetraols in highly stereoselective reactions. The antimicrobial activity of aminodiol and aminotriol derivatives as well as di-, tri- and tetraols was also explored. In addition, structure\u2013activity relationships were examined by assessing substituent effects on the aminodiol and aminotriol systems.<\/jats:p>","DOI":"10.3390\/ijms20164050","type":"journal-article","created":{"date-parts":[[2019,8,19]],"date-time":"2019-08-19T11:22:38Z","timestamp":1566213758000},"page":"4050","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Stereoselective Synthesis and Investigation of Isopulegol-Based Chiral Ligands"],"prefix":"10.3390","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8296-887X","authenticated-orcid":false,"given":"Tam Minh","family":"Le","sequence":"first","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"},{"name":"Stereochemistry Research Group of the Hungarian Academy of Sciences, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1421-286X","authenticated-orcid":false,"given":"Tam\u00e1s","family":"Szilasi","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bettina","family":"Volford","sequence":"additional","affiliation":[{"name":"Department of Microbiology, University of Szeged, 6726 Szeged, K\u00f6z\u00e9p fasor 52, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1651-4623","authenticated-orcid":false,"given":"Andr\u00e1s","family":"Szekeres","sequence":"additional","affiliation":[{"name":"Department of Microbiology, University of Szeged, 6726 Szeged, K\u00f6z\u00e9p fasor 52, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1066-5287","authenticated-orcid":false,"given":"Ferenc","family":"F\u00fcl\u00f6p","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"},{"name":"Stereochemistry Research Group of the Hungarian Academy of Sciences, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2432-8409","authenticated-orcid":false,"given":"Zsolt","family":"Szakonyi","sequence":"additional","affiliation":[{"name":"Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"},{"name":"Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, E\u00f6tv\u00f6s utca 6, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,8,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1495","DOI":"10.1002\/chem.201303867","article-title":"A pyrimidopyrimidine Janus-AT nucleoside with improved base-pairing properties to both A and T within a DNA duplex: The stabilizing effect of a second endocyclic ring nitrogen","volume":"20","author":"Largy","year":"2014","journal-title":"Chem. 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