{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:33:00Z","timestamp":1786977180038,"version":"build-2736575974"},"reference-count":24,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2006,1,4]],"date-time":"2006-01-04T00:00:00Z","timestamp":1136332800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biotech &amp;amp; Bioengineering"],"published-print":{"date-parts":[[2006,3,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A pilot scale whole cell process was developed for the enantioselective 1,2\u2010reduction of prochiral \u03b1,\u03b2\u2010unsaturated ketone to (\n                    <jats:italic>R<\/jats:italic>\n                    ) allylic alcohol using\n                    <jats:italic>Candida chilensis<\/jats:italic>\n                    . Initial development showed high enantiomeric excess (EE\u2009&gt;\u200995%) but low product yield (10%). Process development, using a combination of statistically designed screening and optimization experiments, improved the desired alcohol yield to 90%. The fermentation growth stage, particularly medium composition and growth pH, had a significant impact on the bioconversion while process characterization identified diverse challenges including the presence of multiple enzymes, substrate\/product toxicity, and biphasic cellular morphology. Manipulating the fermentation media allowed control of the whole cell morphology to a predominately unicellular broth, away from the viscous pseudohyphae, which were detrimental to the bioconversion. The activity of a competing enzyme, which produced the undesired saturated ketone and (\n                    <jats:italic>R<\/jats:italic>\n                    ) saturated alcohol, was minimized to \u22645% by controlling the reaction pH, temperature, substrate concentration, and biomass level. Despite the toxicity effects limiting the volumetric productivity, a reproducible and scaleable process was demonstrated at pilot scale with high enantioselectivity (EE\u2009&gt;\u200995%) and overall yield greater than 80%. This was the preferred route compared to a partially purified process using ultra centrifugation, which led to improved volumetric productivity but reduced yield (g\/day). The whole cell approach proved to be a valuable alternative to chemical reduction routes, as an intermediate step for the asymmetric synthesis of an integrin receptor anatagonist for the inhibition of bone resorption and treatment of osteoporosis. \u00a9 2006 Wiley Periodicals, Inc.\n                  <\/jats:p>","DOI":"10.1002\/bit.20751","type":"journal-article","created":{"date-parts":[[2006,1,4]],"date-time":"2006-01-04T19:46:53Z","timestamp":1136404013000},"page":"674-686","source":"Crossref","is-referenced-by-count":36,"title":["Asymmetric reduction of \u03b1, \u03b2\u2010unsaturated ketone to (\n                    <i>R<\/i>\n                    ) allylic alcohol by\n                    <i>Candida chilensis<\/i>"],"prefix":"10.1002","volume":"93","author":[{"given":"D.J.","family":"Pollard","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"K.","family":"Telari","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J.","family":"Lane","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"G.","family":"Humphrey","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"C.","family":"McWilliams","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S.","family":"Nidositko","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"P.","family":"Salmon","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J.","family":"Moore","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2006,1,4]]},"reference":[{"key":"e_1_2_1_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1381-1177(00)00170-3"},{"key":"e_1_2_1_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0032-9592(00)00262-4"},{"key":"e_1_2_1_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm049874c"},{"key":"e_1_2_1_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(98)00432-7"},{"key":"e_1_2_1_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600830420"},{"key":"e_1_2_1_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)89310-8"},{"key":"e_1_2_1_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(94)02190-M"},{"key":"e_1_2_1_9_1","first-page":"53","volume-title":"Applied microbial physiology\u2014A practical approach","author":"Greasham R","year":"1996"},{"key":"e_1_2_1_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02069016"},{"key":"e_1_2_1_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(01)00172-0"},{"key":"e_1_2_1_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(97)10490-7"},{"key":"e_1_2_1_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2003.10.123"},{"key":"e_1_2_1_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/bit.10323"},{"key":"e_1_2_1_15_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.69.2633"},{"key":"e_1_2_1_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s002530100599"},{"key":"e_1_2_1_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19950002969"},{"key":"e_1_2_1_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-7799(99)01351-7"},{"key":"e_1_2_1_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(03)00526-3"},{"key":"e_1_2_1_20_1","doi-asserted-by":"publisher","DOI":"10.1007\/s004490100260"},{"key":"e_1_2_1_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/bit.10204"},{"key":"e_1_2_1_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0958-1669(00)00111-7"},{"key":"e_1_2_1_23_1","unstructured":"SturrM BoydR GbewonyoK Nti\u2010GyabaahJ PollardD McWilliamsC TelariK.2002.Preparation of chiral allylic alcohol intermediate compounds used in asymmetric synthesis of integrin \u03b1v\u03b23receptor antagonists comprises culturing yeast microorganism in propagation medium and unsaturated ketone substrate. 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