{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T14:51:13Z","timestamp":1791298273296,"version":"4.1.0"},"reference-count":78,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2008,1,10]],"date-time":"2008-01-10T00:00:00Z","timestamp":1199923200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2008,1,25]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Several members of a new family of seven\u2010membered azasugars, which can be seen as 1\u2010azasugar ring homologues, have been obtained by simple chemical transformations starting from a sugar\u2010derived azidolactol. Unlike their piperidine counterparts, these molecules are chemically stable when they possess a hydroxy group at the pseudo\u2010C\u20102 position. Biological assays with a range of carbohydrate\u2010processing enzymes have revealed interesting potential for these compounds. A trihydroxymethyl\u2010substituted azepane displayed strong competitive inhibition on almond \u03b2\u2010glucosidase (<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>=2.5 \u03bc<jats:sc>M<\/jats:sc>) while a trihydroxylated carboxylic acid derivative proved to be a potent and selective <jats:sc>L<\/jats:sc>\u2010fucosidase inhibitor (<jats:italic>K<\/jats:italic><jats:sub>i<\/jats:sub>=41 n<jats:sc>M<\/jats:sc>). N\u2010Butylation of these seven\u2010membered 1\u2010azasugars generated derivatives with some activity towards the Gaucher\u2019s disease\u2010related glucosylceramide transferase (IC<jats:sub>50<\/jats:sub> 75 \u03bc<jats:sc>M<\/jats:sc>) that did not interact significantly with digestive glucosidases.<\/jats:p>","DOI":"10.1002\/cbic.200700496","type":"journal-article","created":{"date-parts":[[2008,1,10]],"date-time":"2008-01-10T11:15:53Z","timestamp":1199963753000},"page":"253-260","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":50,"title":["New Synthetic Seven\u2010Membered 1\u2010Azasugars Displaying Potent Inhibition Towards Glycosidases and Glucosylceramide Transferase"],"prefix":"10.1002","volume":"9","author":[{"given":"Hongqing","family":"Li","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tao","family":"Liu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongmin","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sylvain","family":"Favre","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudia","family":"Bello","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pierre","family":"Vogel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Terry D.","family":"Butters","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nikos G.","family":"Oikonomakos","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00e9r\u00f4me","family":"Marrot","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yves","family":"Bl\u00e9riot","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2008,1,17]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(00)00113-0"},{"key":"e_1_2_6_2_2","volume-title":"Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond","author":"St\u00fctz A. E.","year":"1999"},{"key":"e_1_2_6_3_2","unstructured":"\u00a0"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-9136(199808)15:8<657::AID-DIA652>3.0.CO;2-7"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0003-4509(07)90013-9"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1093\/clinids\/12.5.908"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.2174\/1389200043335513"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/scientificamerican0199-78"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1128\/JVI.76.8.3596-3604.2002"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1177\/095632020101200601"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.2174\/1568026033452456"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1358\/dof.2005.030.06.914820"},{"key":"e_1_2_6_15_2","unstructured":"R. J.Nash M. W.Carroll A. A.Watson G. W. J.Fleet G.Horn PCT Int. Appl.(2007) CODEN: PIXXD2 WO 2007010266 ["},{"key":"e_1_2_6_15_3","first-page":"177231","volume":"146","year":"2007","journal-title":"Chem. Abstr."},{"key":"e_1_2_6_16_2","unstructured":"\u00a0"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.96.21.11878"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.2174\/1568026033452492"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0409019"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.2165\/00003495-200059030-00012"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19941061730"},{"key":"e_1_2_6_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199417781"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973443k"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00016a039"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010240u"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1081\/CAR-200030070"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1080\/10242420500533242"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja953989b"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0896(00)00330-8"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(99)00042-6"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2003.12.040"},{"key":"e_1_2_6_31_2","unstructured":"\u00a0"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1039\/B402542C"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.3987\/COM-04-S(P)45"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2004.12.005"},{"key":"e_1_2_6_34_3","doi-asserted-by":"publisher","DOI":"10.1039\/b518117h"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/B610377D"},{"key":"e_1_2_6_36_2","unstructured":"\u00a0"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1080\/07328309008543848"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)76888-2"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00123a037"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja960975c"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(02)00377-4"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2003.10.003"},{"key":"e_1_2_6_43_2","unstructured":"Selected crystal structure data for compound9(C7H16ClNO3;MW197.66); crystal structure analysis: orthorhombic space groupP212121; dimensions:a=8.4674(3) \u00c5 b=8.5384(3) \u00c5 c=13.2813(4) \u00c5 V=960.21(6) \u00c53;Z=4; total reflections collected: 24\u2009553; independent reflections: 2810 (2624\u2009Fo>4\u2009\u03c3(Fo)); data were collected up to a 2\u0398maxvalue of 60.16 (100\u2009% coverage). Number of variables: 113;R1=0.0239 wR2=0.0611 S=1.050; highest residual electron density 0.24 e\u2009\u00c5\u22123. CCDC 661\u2009992 contains the supplementary crystallographic data. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk\/data_request\/cif"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj20020466"},{"key":"e_1_2_6_45_2","unstructured":"\u00a0"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(00)02161-9"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200600217"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo982448c"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1093\/jnci\/djh256"},{"key":"e_1_2_6_50_2","unstructured":"\u00a0"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(90)84164-P"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1016\/0008-6215(90)84165-Q"},{"key":"e_1_2_6_53_2","unstructured":"\u00a0"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/0003-9861(83)90181-9"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00126a033"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1042\/bst0280150"},{"key":"e_1_2_6_57_2","unstructured":"\u00a0"},{"key":"e_1_2_6_58_2","volume-title":"Gaucher\u2019s Disease","year":"1997"},{"key":"e_1_2_6_59_2","first-page":"229","volume-title":"Drugs Future","author":"Sorbera L. A.","year":"2003"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1742-4658.2006.05410.x"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj20030348"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0957-4166(99)00468-1"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm060496g"},{"key":"e_1_2_6_64_2","unstructured":"\u00a0"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2003.10.003"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600362"},{"key":"e_1_2_6_67_2","first-page":"3439","author":"Macfarlane D. P. S.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja057592b"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ab.2004.03.051"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20031824"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.08.010"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/0167-4838(85)90257-2"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0076-6879(97)76066-X"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444996012255"},{"key":"e_1_2_6_75_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0108767390010224"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbic.200700496","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.200700496","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T15:10:48Z","timestamp":1760281848000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.200700496"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,1,17]]},"references-count":78,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2008,1,25]]}},"alternative-id":["10.1002\/cbic.200700496"],"URL":"https:\/\/doi.org\/10.1002\/cbic.200700496","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"value":"1439-4227","type":"print"},{"value":"1439-7633","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,1,17]]},"assertion":[{"value":"2007-08-27","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2008-01-17","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}