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A rhodium (Rh) complex immobilized in a bipyridine\u2010based periodic mesoporous organosilica (BPy\u2010PMO) shows high catalytic activity during transfer hydrogenation, even in the presence of bovine serum albumin (BSA), while a homogeneous Rh complex exhibits reduced activity due to direct interaction with BSA. The use of a smaller protein or an amino acid revealed a clear size\u2010sieving effect of the BPy\u2010PMO that protected the Rh catalyst from direct interactions. A combination of Rh\u2010immobilized BPy\u2010PMO and an enzyme (horse liver alcohol dehydrogenase; HLADH) promoted sequential reactions involving the transfer hydrogenation of NAD<jats:sup>+<\/jats:sup> to give NADH followed by the asymmetric hydrogenation of 4\u2010phenyl\u20102\u2010butanone with high enantioselectivity. The use of BPy\u2010PMO as a support for metal complexes could be applied to other systems consisting of a metal\u2010complex catalyst and an enzyme.<\/jats:p>","DOI":"10.1002\/anie.201904116","type":"journal-article","created":{"date-parts":[[2019,4,26]],"date-time":"2019-04-26T02:11:23Z","timestamp":1556244683000},"page":"9150-9154","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":76,"title":["Cooperative Catalysis of an Alcohol Dehydrogenase and Rhodium\u2010Modified Periodic Mesoporous Organosilica"],"prefix":"10.1002","volume":"58","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5252-1834","authenticated-orcid":false,"given":"Tomoki","family":"Himiyama","sequence":"first","affiliation":[{"name":"Toyota Central R&amp;D Laboratories, Inc.  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