{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,14]],"date-time":"2025-10-14T07:09:25Z","timestamp":1760425765077,"version":"3.37.3"},"reference-count":74,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2020,2,3]],"date-time":"2020-02-03T00:00:00Z","timestamp":1580688000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/100010665","name":"H2020 Marie Sk\u0142odowska-Curie Actions","doi-asserted-by":"publisher","award":["H2020-MSCA-IF-2015-707071"],"award-info":[{"award-number":["H2020-MSCA-IF-2015-707071"]}],"id":[{"id":"10.13039\/100010665","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-09-BLAN-0082-01"],"award-info":[{"award-number":["ANR-09-BLAN-0082-01"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angewandte Chemie"],"published-print":{"date-parts":[[2020,3,27]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The recognition of either homomeric or heteromeric pairs of pentoses in an aromatic oligoamide double helical foldamer capsule was evidenced by circular dichroism (CD), NMR spectroscopy, and X\u2010ray crystallography. The cavity of the host was predicted to be large enough to accommodate simultaneously two xylose molecules and to form a 1:2 complex (one container, two saccharides). Solution and solid\u2010state data revealed the selective recognition of the \u03b1\u2010<jats:sup>4<\/jats:sup>C<jats:sub>1<\/jats:sub>\u2010<jats:sc>d<\/jats:sc>\u2010xylopyranose tautomer, which is bound at two identical sites in the foldamer cavity. A step further was achieved by sequestering a heteromeric pair of pentoses, that is, one molecule of \u03b1\u2010<jats:sup>4<\/jats:sup>C<jats:sub>1<\/jats:sub>\u2010<jats:sc>d<\/jats:sc>\u2010xylopyranose and one molecule of \u03b2\u2010<jats:sup>1<\/jats:sup>C<jats:sub>4<\/jats:sub>\u2010<jats:sc>d<\/jats:sc>\u2010arabinopyranose despite the symmetrical nature of the host and despite the similarity of the guests. Subtle induced\u2010fit and allosteric effects are responsible for the outstanding selectivities observed.<\/jats:p>","DOI":"10.1002\/ange.201914929","type":"journal-article","created":{"date-parts":[[2019,12,21]],"date-time":"2019-12-21T18:17:30Z","timestamp":1576952250000},"page":"5846-5854","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Allosteric Recognition of Homomeric and Heteromeric Pairs of Monosaccharides by a Foldamer Capsule"],"prefix":"10.1002","volume":"132","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0609-6499","authenticated-orcid":false,"given":"Pedro","family":"Mateus","sequence":"first","affiliation":[{"name":"CBMN (UMR5248) Univ. Bordeaux\u2014 CNRS\u2014 IPB Institut Europ\u00e9en de Chimie et Biologie  2 rue Robert Escarpit 33600 Pessac France"}]},{"given":"Nagula","family":"Chandramouli","sequence":"additional","affiliation":[{"name":"CBMN (UMR5248) Univ. Bordeaux\u2014 CNRS\u2014 IPB Institut Europ\u00e9en de Chimie et Biologie  2 rue Robert Escarpit 33600 Pessac France"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0776-7947","authenticated-orcid":false,"given":"Cameron D.","family":"Mackereth","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Bordeaux CNRS INSERM U1212 (ARNA) Institut Europ\u00e9en de Chimie et Biologie  2 Rue Robert Escarpit 33600 Pessac France"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2932-3255","authenticated-orcid":false,"given":"Brice","family":"Kauffmann","sequence":"additional","affiliation":[{"name":"Universit\u00e9 de Bordeaux CNRS INSERM UMS3033 Institut Europ\u00e9en de Chimie et Biologie (IECB)  2 rue Robert Escarpit 33600 Pessac France"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6552-6914","authenticated-orcid":false,"given":"Yann","family":"Ferrand","sequence":"additional","affiliation":[{"name":"CBMN (UMR5248) Univ. Bordeaux\u2014 CNRS\u2014 IPB Institut Europ\u00e9en de Chimie et Biologie  2 rue Robert Escarpit 33600 Pessac France"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7036-9696","authenticated-orcid":false,"given":"Ivan","family":"Huc","sequence":"additional","affiliation":[{"name":"CBMN (UMR5248) Univ. Bordeaux\u2014 CNRS\u2014 IPB Institut Europ\u00e9en de Chimie et Biologie  2 rue Robert Escarpit 33600 Pessac France"},{"name":"Department Pharmazie and Center for Integrated Protein Science Ludwig-Maximilians-Universit\u00e4t  Butenandtstr. 5\u201313 81377 M\u00fcnchen Germany"}]}],"member":"311","published-online":{"date-parts":[[2020,2,3]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.201800742"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00768C"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0155-z"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2395"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1409"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1148735"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461409"},{"key":"e_1_2_6_9_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200461409"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800390"},{"key":"e_1_2_6_11_1","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201308879"},{"key":"e_1_2_6_12_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201308879"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980904)37:16<2270::AID-ANIE2270>3.0.CO;2-6"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980817)110:16<2397::AID-ANGE2397>3.0.CO;2-Y"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199515961"},{"key":"e_1_2_6_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19951071511"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00052a030"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc10964b"},{"key":"e_1_2_6_17_1","unstructured":"\u00a0"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo301966z"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja043037i"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol047907c"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902514"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol051230r"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.1701126"},{"key":"e_1_2_6_24_1","unstructured":"\u00a0"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja047436p"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol070492l"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604176"},{"key":"e_1_2_6_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200604176"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo800599w"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b02768"},{"key":"e_1_2_6_30_1","unstructured":"\u00a0"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2195"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201808370"},{"key":"e_1_2_6_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201808370"},{"key":"e_1_2_6_33_1","unstructured":"\u00a0"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00075"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b05913"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC04466B"},{"key":"e_1_2_6_37_1","unstructured":"\u00a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9907358"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja020607a"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja037808e"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja029574p"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1039\/b503313f"},{"key":"e_1_2_6_43_1","unstructured":"\u00a0"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0168115"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja020718"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1124985"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja071591x"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja802288k"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9107275"},{"key":"e_1_2_6_50_1","unstructured":"\u00a0"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja048860t"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/B818889K"},{"key":"e_1_2_6_53_1","unstructured":"\u00a0"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1038\/29501"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200462839"},{"key":"e_1_2_6_55_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200462839"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b06195"},{"key":"e_1_2_6_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700847"},{"key":"e_1_2_6_58_1","unstructured":"\u00a0"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CS00062K"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902490"},{"key":"e_1_2_6_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902490"},{"key":"e_1_2_6_61_1","unstructured":"\u00a0"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1038\/35037545"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101697"},{"key":"e_1_2_6_63_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201101697"},{"key":"e_1_2_6_64_1","unstructured":"The diastereomeric excess was calculated here using ([P-complex]\u2212[M-complex])\/([P-complex]+[M-complex])."},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00734"}],"container-title":["Angewandte Chemie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ange.201914929","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ange.201914929","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ange.201914929","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,4]],"date-time":"2023-09-04T13:03:40Z","timestamp":1693832620000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ange.201914929"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,2,3]]},"references-count":74,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2020,3,27]]}},"alternative-id":["10.1002\/ange.201914929"],"URL":"https:\/\/doi.org\/10.1002\/ange.201914929","archive":["Portico"],"relation":{},"ISSN":["0044-8249","1521-3757"],"issn-type":[{"type":"print","value":"0044-8249"},{"type":"electronic","value":"1521-3757"}],"subject":[],"published":{"date-parts":[[2020,2,3]]},"assertion":[{"value":"2019-11-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-02-03","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}