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Here, we report a highly selective biocatalytic direct Prins cyclohydration for the synthesis of (1\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010\n                    <jats:italic>cis<\/jats:italic>\n                    \u2010\n                    <jats:italic>p<\/jats:italic>\n                    \u2010menthane\u20103,8\u2010diol (PMD), a natural insect repellent with high efficacy. By strategically engineering squalene\u2010hopene cyclases (SHCs), we achieved &gt;96% diastereomeric excess, surpassing previous synthetic methods. Structural and mechanistic analyses suggest direct Prins cyclohydration and a precisely positioned water molecule within the enzyme's active pocket adjacent to the final carbocation that drives hydration and catalytic efficiency. Fine\u2010tuning the biocatalytic setup enabled preparative scale production, without losing much product selectivity. Moreover, we demonstrate access to the other naturally occurring PMD isomers from (\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010 and (\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010citronellal, as well as a one\u2010pot cascade starting from\n                    <jats:italic>E<\/jats:italic>\n                    \/\n                    <jats:italic>Z<\/jats:italic>\n                    \u2010citral. This study paves the way for highly selective access to stereodefined terpene\u2010derived repellents and establishes engineered squalene\u2010hopene cyclases as a tool for direct asymmetric Prins cyclohydration.\n                  <\/jats:p>","DOI":"10.1002\/anie.8826784","type":"journal-article","created":{"date-parts":[[2026,4,13]],"date-time":"2026-04-13T12:56:21Z","timestamp":1776084981000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Biocatalytic Access to Natural Mosquito Repellent\n                    <i>p<\/i>\n                    \u2010Menthane\u20103,8\u2010diol via Direct Asymmetric Prins Cyclohydration"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1134-8649","authenticated-orcid":false,"given":"Andreas","family":"Schneider","sequence":"first","affiliation":[{"name":"Institute of Biochemistry and Technical Biochemistry, University of Stuttgart  Vaihingen 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