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The CaADH enzyme is utilized here for synthesizing 20 potential aryl isoserine side chains for the Taxotere family of tubulin\u2010binding chemotherapeutics. The approach involves dynamic reductive kinetic resolution (DYRKR) upon the corresponding \u03b1\u2010chloro\u2010\u03b2\u2010keto esters, showing high D\u2010\n                    <jats:italic>syn<\/jats:italic>\n                    stereoselectivity, including those leading to the clinically relevant milataxel (Ar\u00a0=\u00a02\u2010furyl) and simotaxel (Ar\u00a0=\u00a02\u2010thienyl) side chains. Furthermore, various cross\u2010coupling chemistries performed on the\n                    <jats:italic>p<\/jats:italic>\n                    \u2010bromophenyl isoserine side chain significantly enhance the structural diversity of the taxoid side chain library obtained (16 additional taxoid side chains). The CaADH structure is notable: (i) the nicotinamide cofactor is bound in an\n                    <jats:italic>anti\u2010<\/jats:italic>\n                    conformation, with the amide carbonyl occupying the ketone binding pocket, and (ii) a flexible loop near the active site likely contributes to the remarkable substrate promiscuity observed in CaADH. We present our perspective on the dynamic nature of the CaADH active site through molecular dynamics simulation, proposing a halogen bonding model as a potential mechanism for the remarkable selectivity for an (\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010configured C\u2500Cl bond, in addition to the D\u2010facial selectivity, demonstrated across 20 diverse substrates by this remarkable short\u2010chain dehydrogenase enzyme.\n                  <\/jats:p>","DOI":"10.1002\/anie.202510889","type":"journal-article","created":{"date-parts":[[2025,6,19]],"date-time":"2025-06-19T22:11:09Z","timestamp":1750371069000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Is a Malleable Active Site Loop the Key to High Substrate Promiscuity? Hybrid, Biocatalytic Route to Structurally Diverse Taxoid Side Chains with Remarkable Dual Stereocontrol"],"prefix":"10.1002","volume":"64","author":[{"given":"Gaurav P.","family":"Kudalkar","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Nebraska Lincoln NE 68588\u20100304 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Florian","family":"Leidner","sequence":"additional","affiliation":[{"name":"Theoretical and Computational Biophysics Max\u2010Planck Institute for Multidisciplinary Sciences G\u00f6ttingen 37077 Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nivesh","family":"Kumar","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Nebraska Lincoln NE 68588\u20100304 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jared L.","family":"Hass","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Nebraska Lincoln NE 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