{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T17:52:50Z","timestamp":1790272370906,"version":"4.1.0"},"reference-count":22,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2004,10,1]],"date-time":"2004-10-01T00:00:00Z","timestamp":1096588800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Lipids"],"published-print":{"date-parts":[[2004,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>In this study, the effect of temperature on the stereoselectivity of phospholipase D (PLD) toward the two primary hydroxyl groups of glycerol in the transphosphatidylation reaction of phosphatidylcholine to phosphatidylglycerol (PtdGro) was investigated. For this purpose, PLD from bacteria (<jats:italic>Streptomyces septatus<\/jats:italic> TH\u20102, <jats:italic>S. halstedii<\/jats:italic> subsp. <jats:italic>scabies<\/jats:italic> K6, and <jats:italic>Actinomadura<\/jats:italic> sp.) and cabbage were tested. At the reaction temperatures employed (0\u201360\u00b0C), the proportions of the two PtdGro diastereomers, namely, 1,2\u2010dioleoyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycero\u20103\u2010phospho\u20103\u2032\u2010<jats:italic>sn<\/jats:italic>\u2010glycerol (<jats:italic>R,R<\/jats:italic> configuration) and 1,2\u2010dioleoyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycero\u20103\u2010phosphol\u20101\u2032\u2010<jats:italic>sn<\/jats:italic>\u2010glycerol (<jats:italic>R,S<\/jats:italic> configuration), which were produced with PLD from <jats:italic>Streptomyces<\/jats:italic> TH\u20102 and <jats:italic>Actinomadura<\/jats:italic> sp., changed gradually from 50% <jats:italic>R,R<\/jats:italic> and 50% <jats:italic>R,S<\/jats:italic> at 50\u201360\u00b0C to 70% <jats:italic>R,R<\/jats:italic> and 30% <jats:italic>R,S<\/jats:italic> at O\u00b0C. These alterations suggested that the stereoselectivity of the bacterial PLD toward the two primary hydroxyl groups of prochiral glycerol was significantly influenced by reaction temperature. PLD from <jats:italic>Streptomyces<\/jats:italic> K6 showed relatively little effect of temperature on stereoselectivity, giving 65\u201369% <jats:italic>R,R<\/jats:italic> in the temperature range of 60\u201310\u00b0C examined. The plots of In ([<jats:italic>R,R<\/jats:italic>]\/[<jats:italic>R,S<\/jats:italic>]) vs. 1\/<jats:italic>T<\/jats:italic> gave good linear fits for these three bacterial PLD. No temperature effect was observed for cabbage PLD, which gave an almost equimolar mixture of the <jats:italic>R,R<\/jats:italic> and <jats:italic>R,S<\/jats:italic> diastereomers in the range from 0 to 40\u00b0C. The temperature\u2010dependent change in enantiomeric selectivity of the bacterial PLD promises potentially profitable commercial exploitation.<\/jats:p>","DOI":"10.1007\/s11745-004-1325-0","type":"journal-article","created":{"date-parts":[[2006,11,13]],"date-time":"2006-11-13T19:53:29Z","timestamp":1163447609000},"page":"1019-1023","source":"Crossref","is-referenced-by-count":14,"title":["Effect of temperature on the stereoselectivity of phospholipase D toward glycerol in the transphosphatidylation of phosphatidylcholine to phosphatidylglycerol"],"prefix":"10.1002","volume":"39","author":[{"given":"Rina","family":"Sato","sequence":"first","affiliation":[{"name":"Laboratory of Bioresources Chemistry, Graduate School of Fisheries Sciences Hokkaido University 3\u20101\u20101 Minato\u2010cho, Hakodate Hokkaido 041\u20108611 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yutaka","family":"Itabashi","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources Chemistry, Graduate School of Fisheries Sciences Hokkaido University 3\u20101\u20101 Minato\u2010cho, Hakodate Hokkaido 041\u20108611 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akira","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources Chemistry, Graduate School of Fisheries Sciences Hokkaido University 3\u20101\u20101 Minato\u2010cho, Hakodate Hokkaido 041\u20108611 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tadashi","family":"Hatanaka","sequence":"additional","affiliation":[{"name":"Research Institute for Biological Sciences Okayama 716\u2010214 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arnis","family":"Kuksis","sequence":"additional","affiliation":[{"name":"Banting and Best Department of Medical Research University of Toronto Toronto Ontario M5G 1L6 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2004,10]]},"reference":[{"key":"e_1_2_2_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-024916-9.50011-1"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4684-5353-9_5"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejlt.200390060"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)96298-8"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-3084(76)90071-2"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1997.2418"},{"key":"e_1_2_2_8_1","doi-asserted-by":"publisher","DOI":"10.1023\/A:1005644032415"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11745-004-1324-1"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-4838(02)00363-1"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbapap.2003.09.013"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01747-X"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo970581j"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/0167-7799(96)80908-5"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00165a057"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja026512q"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/1097-0290(20010205)72:3<374::AID-BIT16>3.0.CO;2-E"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00389a064"},{"key":"e_1_2_2_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2004.04.003"},{"key":"e_1_2_2_20_1","first-page":"215","volume-title":"Phospholipids","author":"Hostetler K.Y.","year":"1982"},{"key":"e_1_2_2_21_1","doi-asserted-by":"crossref","unstructured":"Fujishima H. Gamano T. Taoka Y. Sawabe T. andItabashi Y.(2004)Stereoisomers of Marine Bacterial Phosphatidylglycerols Nippon Suisan Gakkaishi(in Japanese)70 200\u2013202.","DOI":"10.2331\/suisan.70.200"},{"key":"e_1_2_2_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(19)77408-0"},{"key":"e_1_2_2_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-3084(88)90032-1"}],"container-title":["Lipids"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/pdf\/10.1007\/s11745-004-1325-0","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T14:01:24Z","timestamp":1760968884000},"score":1,"resource":{"primary":{"URL":"https:\/\/aocs.onlinelibrary.wiley.com\/doi\/10.1007\/s11745-004-1325-0"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2004,10]]},"references-count":22,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2004,10]]}},"alternative-id":["10.1007\/s11745-004-1325-0"],"URL":"https:\/\/doi.org\/10.1007\/s11745-004-1325-0","archive":["Portico"],"relation":{},"ISSN":["0024-4201","1558-9307"],"issn-type":[{"value":"0024-4201","type":"print"},{"value":"1558-9307","type":"electronic"}],"subject":[],"published":{"date-parts":[[2004,10]]}}}