{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,23]],"date-time":"2026-09-23T18:29:44Z","timestamp":1790188184235,"version":"4.1.0"},"reference-count":24,"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>Using chiral\u2010phase HPLC, we determined the stereochemical configuration of the phosphatidylglycerols (PtdGro) synthesized <jats:italic>in vitro<\/jats:italic> from 1,2\u2010diacyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycero\u20103\u2010phosphocholine (PtdCho, <jats:italic>R<\/jats:italic> configuration) or 1,2\u2010diacyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycero\u20103\u2010phosphoethanolamine (PtdEtn, <jats:italic>R<\/jats:italic> configuration) and glycerol by transphosphatidylation with bacterial phospholipase D (PLD). The results obtained with PLD preparations from three <jats:italic>Streptomyces<\/jats:italic> strains (<jats:italic>S. septatus<\/jats:italic> TH\u20102, <jats:italic>S. halstedii<\/jats:italic> K5, and <jats:italic>S. halstedii<\/jats:italic> subsp. <jats:italic>scabies<\/jats:italic> K6) and one <jats:italic>Actinomadura<\/jats:italic> species were compared with those obtained using cabbage and peanut PLD. The reaction was carried out at 30\u00b0C in a biphasic system consisting of diethyl ether and acetate buffer. The resulting PtdGro were then converted into bis(3,5\u2010dinitrophenylurethane) derivatives, which were separated on an (<jats:italic>R<\/jats:italic>)\u20101\u2010(1\u2010naphthyl)ethylamine polymer. In contrast to the cabbage and peanut PLD, which gave equimolar mixtures of the <jats:italic>R,S<\/jats:italic> and <jats:italic>R,R<\/jats:italic> diastereomers, as previously established, the bacterial PLD yielded diastereomixtures of 30\u201340% 1,2\u2010diacyl\u2010<jats:italic>sn<\/jats:italic>\u2010glycero\u20103\u2010phospho\u20101\u2032\u2010<jats:italic>sn<\/jats:italic>\u2010glycerol (<jats:italic>R,S<\/jats:italic> configuration) and 60\u201370% 1,2\u2010diacyl\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). The highest disproportionation was found for the <jats:italic>Streptomyces<\/jats:italic> K6 species. The present study demonstrates that bacterial PLD\u2010catalyzed transphosphatidylation proceeds to a considerable extent stereoselectively to produce PtdGro from PtdCho or PtdEtn and prochiral glycerol, indicating a preference for the sn\u20103\u2032 position of the glycerol molecule.<\/jats:p>","DOI":"10.1007\/s11745-004-1324-1","type":"journal-article","created":{"date-parts":[[2006,11,13]],"date-time":"2006-11-13T19:53:29Z","timestamp":1163447609000},"page":"1013-1018","source":"Crossref","is-referenced-by-count":15,"title":["Asymmetric <i>in vitro<\/i> synthesis of diastereomeric phosphatidylglycerols from phosphatidylcholine and glycerol by bacterial phospholipase D"],"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":"Tadashi","family":"Hatanaka","sequence":"additional","affiliation":[{"name":"Research Institute for Biological Sciences Okayama 716\u20101241 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\/S0021-9258(18)96298-8"},{"key":"e_1_2_2_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-024916-9.50011-1"},{"key":"e_1_2_2_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4684-5353-9_5"},{"key":"e_1_2_2_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejlt.200390060"},{"key":"e_1_2_2_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/0005-2760(89)90233-6"},{"key":"e_1_2_2_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-7799(97)01012-3"},{"key":"e_1_2_2_8_1","first-page":"219","volume-title":"Enzymes in Lipid Modification","author":"Ulbrich\u2010Hofmann R.","year":"2000"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(75)90574-4"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/0009-3084(76)90071-2"},{"key":"e_1_2_2_11_1","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1997.2418"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1023\/A:1005644032415"},{"key":"e_1_2_2_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0141-0229(02)00121-7"},{"key":"e_1_2_2_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-4838(02)00363-1"},{"key":"e_1_2_2_15_1","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1999.4353"},{"key":"e_1_2_2_16_1","doi-asserted-by":"publisher","DOI":"10.5650\/jos1996.48.559"},{"key":"e_1_2_2_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2275(20)40272-X"},{"key":"e_1_2_2_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/0141-0229(87)90058-5"},{"key":"e_1_2_2_19_1","first-page":"1946","article-title":"Purification and Properties of Phospholipase D from Streptomyces antibioticus","volume":"57","author":"Shimbo K.","year":"1993","journal-title":"Agric. 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