{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T12:50:05Z","timestamp":1790859005360,"version":"4.1.0"},"reference-count":69,"publisher":"Wiley","issue":"51","license":[{"start":{"date-parts":[[2011,11,16]],"date-time":"2011-11-16T00:00:00Z","timestamp":1321401600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2011,12,16]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    <jats:italic>Helicobacter pylori<\/jats:italic>\n                    is a common cause of gastroduodenal inflammatory diseases such as chronic gastritis and peptic ulcers and also an important factor in gastric carcinogenesis. Recent reports have demonstrated that bacterial inflammatory processes, such as stimulation with\n                    <jats:italic>H.\u2005pylori<\/jats:italic>\n                    lipopolysaccharide (LPS), initiate atherosclerosis. To establish the structures responsible for the inflammatory response of\n                    <jats:italic>H.\u2005pylori<\/jats:italic>\n                    LPS, we synthesized various kinds of lipid\u2005A structures (i.e., triacylated lipid\u2005A and Kdo\u2010lipid\u2005A compounds), with or without the ethanolamine group at the 1\u2010phosphate moiety, by a new divergent synthetic route. Stereoselective \u03b1\u2010glycosylation of Kdo\n                    <jats:italic>N<\/jats:italic>\n                    \u2010phenyltrifluoroacetimidate was achieved by use of microfluidic methods. None of the lipid\u2005A and Kdo\u2010lipid\u2005A compounds were a strong inducer of IL\u20101\u03b2, IL\u20106, or IL\u20108, suggesting that\n                    <jats:italic>H.\u2005pylori<\/jats:italic>\n                    LPS is unable to induce acute inflammation. In fact, the lipid\u2005A and Kdo\u2010lipid\u2005A compounds showed antagonistic activity against cytokine induction by\n                    <jats:italic>E.\u2005coli<\/jats:italic>\n                    LPS, except for the lipid\u2005A compound with the ethanolamine group, which showed very weak agonistic activity. On the other hand, these\n                    <jats:italic>H.\u2005pylori<\/jats:italic>\n                    LPS partial structures showed potent IL\u201018\u2010 and IL\u201012\u2010inducing activities. IL\u201018 has been shown to correlate with chronic inflammation, so\n                    <jats:italic>H.\u2005pylori<\/jats:italic>\n                    LPS might be implicated in the chronic inflammatory responses induced by\n                    <jats:italic>H.\u2005pylori<\/jats:italic>\n                    . These results also indicated that\n                    <jats:italic>H.\u2005pylori<\/jats:italic>\n                    LPS can modulate the immune response: NF\u2010\u03baB activation through hTLR4\/MD\u20102 was suppressed, whereas production of IL\u201018 and IL\u201012 was promoted.\n                  <\/jats:p>","DOI":"10.1002\/chem.201003581","type":"journal-article","created":{"date-parts":[[2011,11,17]],"date-time":"2011-11-17T02:38:48Z","timestamp":1321497528000},"page":"14464-14474","source":"Crossref","is-referenced-by-count":82,"title":["Chemical Synthesis of\n                    <i>Helicobacter pylori<\/i>\n                    Lipopolysaccharide Partial Structures and their Selective Proinflammatory Responses"],"prefix":"10.1002","volume":"17","author":[{"given":"Atsushi","family":"Shimoyama","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akinori","family":"Saeki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Natsuko","family":"Tanimura","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroko","family":"Tsutsui","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kensuke","family":"Miyake","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yasuo","family":"Suda","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yukari","family":"Fujimoto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Koichi","family":"Fukase","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2011,11,16]]},"reference":[{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.micro.54.1.615"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/path.1868"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1053\/j.gastro.2005.06.032"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1053\/j.gastro.2005.11.025"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1083-4389.2004.00237.x"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1093\/infdis\/170.1.135"},{"key":"e_1_2_7_6_2","doi-asserted-by":"crossref","first-page":"1183","DOI":"10.1128\/iai.63.4.1183-1187.1995","volume":"63","author":"Perez\u2010Perez G. I.","year":"1995","journal-title":"Infect. Immun."},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0042-6822(02)00026-0"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/ni1386"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1056\/NEJM199901143400207"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(97)03079-1"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1136\/hrt.81.3.245"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.92.15.6911"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1086\/315596"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9150(02)00043-6"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1902\/annals.2002.7.1.72"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1177\/154405910608500202"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.atherosclerosis.2006.03.018"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.2741\/2822"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1462-5822.2007.00935.x"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jalz.2008.12.001"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1038\/378088a0"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1186\/1475-2840-9-11"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1186\/1742-2094-7-9"},{"key":"e_1_2_7_24_2","doi-asserted-by":"publisher","DOI":"10.1086\/318541"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1749-6632.2002.tb04125.x"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.4049\/jimmunol.180.2.1207"},{"key":"e_1_2_7_27_2","unstructured":"Y. Suda Y. Kim K. Nagata Y. Hasegawa A. Kawaguchi M. Oikawa K. Nakajima K. Aoyama T. Ogawa T. Shimoyama T. Tamura S. Kusumoto Symposium Papers: Symposium on the Chemistry of Natural Products2001 43 383\u2013388."},{"key":"e_1_2_7_28_2","first-page":"415","volume-title":"Microbial Glycobiology: Structures, Relevance and Applications","author":"Kusumoto S.","year":"2009"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.81.796"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1177\/09680519050110060901"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.07.036"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1093\/oxfordjournals.jbchem.a021705"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1128\/jb.179.20.6453-6463.1997"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)01158-8"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2249.2007.03346.x"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1399-302X.2007.00392.x"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1039\/b809090d"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00133-1"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja068922a"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200701165"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)01619-7"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200700305"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)93973-X"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39780000694"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1982.1281"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(00)82072-6"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00005a055"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00216a007"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010417)113:8<1523::AID-ANGE1523>3.0.CO;2-X"},{"key":"e_1_2_7_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010417)40:8<1475::AID-ANIE1475>3.0.CO;2-V"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)00157-5"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2004.11.042"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/op0680136"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1080\/07328300701634796"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-695X.1995.tb00181.x"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0928-8244(03)00093-2"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M401231200"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M110.115204"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.0105-2896.2004.00205.x"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.immunol.19.1.423"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0952-7915(98)80163-5"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jhep.2009.03.027"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.immuni.2007.03.008"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1093\/intimm\/dxp017"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1189\/jlb.0408228"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1086\/590158"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1039\/b704427e"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2007.05.012"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201003581","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201003581","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T08:57:53Z","timestamp":1760259473000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201003581"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,11,16]]},"references-count":69,"journal-issue":{"issue":"51","published-print":{"date-parts":[[2011,12,16]]}},"alternative-id":["10.1002\/chem.201003581"],"URL":"https:\/\/doi.org\/10.1002\/chem.201003581","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,11,16]]}}}