{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T07:38:45Z","timestamp":1790753925049,"version":"4.1.0"},"reference-count":55,"publisher":"Wiley","issue":"47","license":[{"start":{"date-parts":[[2018,10,19]],"date-time":"2018-10-19T00:00:00Z","timestamp":1539907200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100000038","name":"Natural Sciences and Engineering Research Council of Canada","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000038","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003178","name":"Alberta Glycomics Centre","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003178","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,11,19]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The <jats:italic>O<\/jats:italic>\u2010methyl phosphoramidate (MeOPN) motif is a non\u2010stoichiometric modification of capsular polysaccharides (CPS) in \u224870\u2009% of all <jats:italic>Campylobacter jejuni<\/jats:italic> strains. Infections by <jats:italic>C. jejuni<\/jats:italic> lead to food\u2010borne illnesses and the CPS they produce are key virulence factors. The MeOPN phosphorus atom in these CPS is stereogenic and is found as a single stereoisomer. However, to date, the absolute stereochemistry at this atom has been undefined. We report the synthesis of the three repeating units found in <jats:italic>C. jejuni<\/jats:italic> 81\u2010176 CPS; one of these possesses a MeOPN group. In the course of these studies we established that the stereochemistry of the phosphorus atom in this MeOPN group is <jats:italic>R<\/jats:italic>. These studies represent the first unequivocal proof of stereochemistry of this group in any <jats:italic>C. jejuni<\/jats:italic> CPS. The compounds produced are anticipated to be useful tools in investigations targeting the function and biosynthesis of this structurally\u2010interesting modification, which so far has only been identified in campylobacter.<\/jats:p>","DOI":"10.1002\/anie.201810222","type":"journal-article","created":{"date-parts":[[2018,10,3]],"date-time":"2018-10-03T04:35:27Z","timestamp":1538541327000},"page":"15592-15596","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["Synthesis of the <i>Campylobacter jejuni<\/i> 81<b>\u2010<\/b>176 Strain Capsular Polysaccharide Repeating Unit Reveals the Absolute Configuration of its <i>O<\/i>\u2010Methyl Phosphoramidate Motif"],"prefix":"10.1002","volume":"57","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8905-2370","authenticated-orcid":false,"given":"V. Narasimharao","family":"Thota","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Alberta T6G 2G2 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5221-4401","authenticated-orcid":false,"given":"Michael J.","family":"Ferguson","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Alberta T6G 2G2 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4022-3041","authenticated-orcid":false,"given":"Ryan P.","family":"Sweeney","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Alberta T6G 2G2 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8331-8211","authenticated-orcid":false,"given":"Todd L.","family":"Lowary","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Alberta  Edmonton Alberta T6G 2G2 Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,10,19]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","doi-asserted-by":"publisher","DOI":"10.1079\/WPS19980004"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1097\/MOG.0b013e328333d73b"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41579-018-0037-9"},{"key":"e_1_2_2_5_1","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1086\/513800"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.it.2003.12.004"},{"key":"e_1_2_2_8_1","unstructured":"\u00a0"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1128\/JCM.12.3.304-309.1980"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF02019474"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1128\/JCM.02348-10"},{"key":"e_1_2_2_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tim.2008.07.002"},{"key":"e_1_2_2_13_1","unstructured":"\u00a0"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1128\/IAI.01056-08"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.00027-17"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1186\/s13104-015-1203-z"},{"key":"e_1_2_2_17_1","unstructured":"\u00a0"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b04824"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.7b00905"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.8b00279"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biochem.8b00811"},{"key":"e_1_2_2_22_1","unstructured":"\u00a0"},{"key":"e_1_2_2_23_2","first-page":"509","volume":"69","author":"Pakulski Z.","year":"1995","journal-title":"Polish J. Chem."},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527208785161169"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.2174\/1385272819666140527231937"},{"key":"e_1_2_2_26_1","unstructured":"\u00a0"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(92)84003-B"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2005.06.023"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1128\/JB.188.9.3273-3279.2006"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M301273200"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1128\/CMR.17.3.581-611.2004"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2958.2004.04374.x"},{"key":"e_1_2_2_34_1","unstructured":"\u00a0"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF02980097"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.5012\/bkcs.2004.25.2.289"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.5012\/bkcs.2008.29.7.1315"},{"key":"e_1_2_2_38_1","unstructured":"\u00a0"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(03)01647-2"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.3987\/REV-08-SR(N)4"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01685"},{"key":"e_1_2_2_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(92)84105-2"},{"key":"e_1_2_2_43_1","unstructured":"\u00a0"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol500894k"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB01017A"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2015.09.012"},{"key":"e_1_2_2_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2008.08.024"},{"key":"e_1_2_2_48_1","unstructured":"\u00a0"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/jr9450000660"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.10.117"},{"key":"e_1_2_2_51_1","unstructured":"Crystallographic data for19: C81H110N5O18PSi Mr=1500.79 colourless needle 0.38\u00d70.06\u00d70.05\u2005mm orthorhombic P212121(No. 19) a=15.1429(3)\u2005\u00c5 b=20.0680(4)\u2005\u00c5 c=26.8195(6)\u2005\u00c5 V=8150.1(3)\u2005\u00c53 Z=4 \u03c1calcd=1.223\u2005g\u2009cm\u22123 \u03bc=1.008\u2005mm\u22121 Cu K\u03b1 (1.54178) T=\u2212100\u2009\u00b0C 2\u03b8 limit=144.77\u00b0 no. of measured (48945) and independent (15989) reflections Rint=0.0513 R1=0.0436 wR2=0.1137 largest difference peak and hole 0.282 and \u22120.333\u2005e\u2009\u00c5\u22123. Data were collected on a Bruker D8 diffractometer equipped with a Cu microfocus source and an APEX\u2005II CCD detector using 1.0\u00b0\u03c9and\u03c6scans and 15\u2005s exposures. Face-indexed absorption corrections were performed using SADABS-2016. The structure was solved using intrinsic phasing method of SHELXT-2014 and refined with the program SHELXL-2018. The CIF has been deposited at the Cambridge Crystallographic Data Centre (CCDC1866111) and can be obtained free of charge viahttps:\/\/www.ccdc.cam.ac.uk\/structures\/."},{"key":"e_1_2_2_52_1","unstructured":"A common mistake in assigning Cahn-Ingold-Prelog priorities is to view P+\u2212O\u2212as P=O. See"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.196603851"},{"key":"e_1_2_2_53_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19660780803"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200991x"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201810222","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201810222","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201810222","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201810222","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,10]],"date-time":"2023-09-10T19:56:27Z","timestamp":1694375787000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201810222"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,10,19]]},"references-count":55,"journal-issue":{"issue":"47","published-print":{"date-parts":[[2018,11,19]]}},"alternative-id":["10.1002\/anie.201810222"],"URL":"https:\/\/doi.org\/10.1002\/anie.201810222","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,10,19]]},"assertion":[{"value":"2018-09-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-10-19","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}