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To date, most of the enzymes encoded in the biosynthetic gene cluster for butirosin, from the producing strain <jats:italic>Bacillus circulans<\/jats:italic>, have been characterized. A few unknown functional proteins, including nicotinamide adenine dinucleotide cofactor\u2010dependent dehydrogenase\/reductase (BtrE and BtrF), are supposed to be involved in the epimerization at C\u20103\u2032\u2032 of butirosin B\/ribostamycin but remain to be characterized. Herein, the conversion of ribostamycin to xylsostasin by BtrE and BtrF in the presence of NAD<jats:sup>+<\/jats:sup> and NADPH was demonstrated. BtrE oxidized the C\u20103\u2032\u2032 of ribostamycin with NAD<jats:sup>+<\/jats:sup> to yield 3\u2032\u2032\u2010oxoribostamycin. BtrF then reduced the generated 3\u2032\u2032\u2010oxoribostamycin with NADPH to produce xylostasin. This reaction step was the last piece of butirosin biosynthesis to be described.<\/jats:p>","DOI":"10.1002\/cbic.201402612","type":"journal-article","created":{"date-parts":[[2015,1,19]],"date-time":"2015-01-19T15:28:15Z","timestamp":1421681295000},"page":"487-495","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Epimerization at C\u20103\u2032\u2032 in Butirosin Biosynthesis by an NAD<sup>+<\/sup>\u2010Dependent Dehydrogenase BtrE and an NADPH\u2010Dependent Reductase BtrF"],"prefix":"10.1002","volume":"16","author":[{"given":"Ryohei","family":"Takeishi","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fumitaka","family":"Kudo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mario","family":"Numakura","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tadashi","family":"Eguchi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,1,19]]},"reference":[{"key":"e_1_2_7_1_2","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)96933-3"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)96934-5"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)96935-7"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0076-6879(09)04620-5"},{"key":"e_1_2_7_6_2","unstructured":"\u00a0"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.52.81"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.52.559"},{"key":"e_1_2_7_9_2","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/b209799k"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.55.1016"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0445948"},{"key":"e_1_2_7_13_2","unstructured":"\u00a0"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja072481t"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi800509x"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604194"},{"key":"e_1_2_7_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604194"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200700717"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200600371"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.04.040"},{"key":"e_1_2_7_20_2","unstructured":"\u00a0"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2005.04.010"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.chembiol.2007.02.005"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.5.6.578"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.32.18"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2005.104"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1007\/10_2009_55"},{"key":"e_1_2_7_27_2","unstructured":"\u00a0"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.32.1280"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb1961.43.2579"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1006\/bbrc.1997.6519"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1096\/fasebj.10.11.8836039"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2004.08.020"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/0959-440X(95)80010-7"},{"key":"e_1_2_7_34_2","unstructured":"\u00a0"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.23.155"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.2.2.79"},{"key":"e_1_2_7_37_2","unstructured":"\u00a0"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.53.1158"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1038\/ja.2005.47"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1039\/b100492l"},{"key":"e_1_2_7_41_2","unstructured":"\u00a0"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.187.23.8020-8025.2005"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja211042r"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1171583"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1742-4658.2008.06395.x"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja507759f"},{"key":"e_1_2_7_47_2","unstructured":"\u00a0"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1993.tb17581.x"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0969-2126(00)00040-X"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.68.2451"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbic.201402612","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.10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