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However, conventional chemical routes remain limited by tetrahydroxylation step that relies on highly toxic osmium tetroxide in combination with costly chiral ligands, whereas the Baeyer\u2010Villiger oxidation step requires strong oxidants and often exhibits limited regioselective control. In this work, optimization of tetrahydroxylation was achieved using the Shing\u2010Plietker reaction, thereby avoiding the use of osmium tetroxide. Moreover, an engineered Baeyer\u2010Villiger monooxygenase (CpnB_BL) was heterologously expressed and used for regioselective B\u2010ring lactonization under mild conditions. A ZIF\u20108\u2010based immobilization strategy was established for this engineered enzyme, further improving its stability and solvent tolerance, and increasing the isolated yield of the Baeyer\u2010Villiger step to 83%. These optimized strategies were subsequently applied to the total synthesis of 28\u2010epi\u2010HBL, achieving an overall yield of 44.9%. This represents a marked improvement over the highest previously reported yield in the literature, which stands at approximately 20%. Collectively, this study lays the groundwork for the development of more precise and sustainable synthetic routes to 28\u2010epi\u2010HBL.<\/jats:p>","DOI":"10.1002\/bit.70373","type":"journal-article","created":{"date-parts":[[2026,9,6]],"date-time":"2026-09-06T18:45:30Z","timestamp":1788720330000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["A Green Chemoenzymatic Route to 28\u2010epi\u2010Homobrassinolide Enabled by OsO\n                    <sub>4<\/sub>\n                    \u2010Free Strategy and Engineered Baeyer\u2010Villiger Monooxygenase With MOF Immobilization"],"prefix":"10.1002","author":[{"given":"Chuanyu","family":"Fu","sequence":"first","affiliation":[{"name":"State Key Laboratory of Microbial Technology, Jiangsu Key Laboratory for Peptide Biosynthesis, School of Food Science and Pharmaceutical Engineering Nanjing Normal University Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ruoyu","family":"Jiao","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Microbial Technology, Jiangsu Key Laboratory for Peptide Biosynthesis, School of Food Science and Pharmaceutical Engineering Nanjing Normal University Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yunyijie","family":"Zhou","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Microbial Technology, Jiangsu Key Laboratory for Peptide Biosynthesis, School of Food Science and Pharmaceutical Engineering Nanjing Normal University Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-1358-1797","authenticated-orcid":false,"given":"Yamei","family":"Lin","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Microbial Technology, Jiangsu Key Laboratory for Peptide Biosynthesis, School of Food Science and Pharmaceutical Engineering Nanjing Normal University Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2699-3448","authenticated-orcid":false,"given":"Xing","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Microbial Technology, Jiangsu Key Laboratory for Peptide Biosynthesis, School of Food Science and Pharmaceutical Engineering Nanjing Normal University Nanjing Jiangsu China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,6]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biotechadv.2023.108299"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-025-96783-0"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jcim.8b00697"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2GC02866B"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b04457"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1515\/biolog-2015-0085"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-021-00613-z"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1093\/bioinformatics\/btz184"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm200028h"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4RA03914A"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3GC04191C"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/281216a0"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pbi.2011.05.004"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms24119377"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c01136"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1128\/AEM.68.11.5671-5684.2002"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA04033G"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-36007-z"},{"key":"e_1_2_9_20_1","first-page":"129","volume-title":"Methods in Enzymology","author":"Jones B. 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