{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T05:56:31Z","timestamp":1790661391730,"version":"4.1.0"},"reference-count":61,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2017,3,1]],"date-time":"2017-03-01T00:00:00Z","timestamp":1488326400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"funder":[{"DOI":"10.13039\/100008656","name":"FINOVI foundation","doi-asserted-by":"crossref","award":["AO9-07"],"award-info":[{"award-number":["AO9-07"]}],"id":[{"id":"10.13039\/100008656","id-type":"DOI","asserted-by":"crossref"}]},{"name":"TEREOS and the Association Nationale de la Recherche et de la Technologie (ANRT)","award":["2011\/1660"],"award-info":[{"award-number":["2011\/1660"]}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2017,3]]},"DOI":"10.1016\/j.ejmech.2017.01.038","type":"journal-article","created":{"date-parts":[[2017,1,25]],"date-time":"2017-01-25T00:59:38Z","timestamp":1485305978000},"page":"98-106","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":26,"special_numbering":"C","title":["Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers"],"prefix":"10.1016","volume":"128","author":[{"given":"Dorine","family":"Belmessieri","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Charlotte","family":"Gozlan","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marie-Christine","family":"Duclos","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Val\u00e9rie","family":"Molinier","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean-Marie","family":"Aubry","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oana","family":"Dumitrescu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"G\u00e9rard","family":"Lina","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andreas","family":"Redl","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicolas","family":"Duguet","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marc","family":"Lemaire","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2017.01.038_bib1","series-title":"Antimicrobial Agents","year":"2012"},{"key":"10.1016\/j.ejmech.2017.01.038_bib2","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3389\/fmicb.2012.00287","volume":"3","author":"Lucera","year":"2012","journal-title":"Front. Microbiol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib3a","doi-asserted-by":"crossref","first-page":"408","DOI":"10.1111\/j.1365-2621.2003.tb05687.x","volume":"68","author":"Suppakul","year":"2003","journal-title":"J.\u00a0Food Sci."},{"key":"10.1016\/j.ejmech.2017.01.038_bib3b","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1016\/S0309-1740(02)00121-3","volume":"62","author":"Quintavalla","year":"2002","journal-title":"Meat Sci."},{"key":"10.1016\/j.ejmech.2017.01.038_bib3c","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/S1466-8564(02)00012-7","volume":"3","author":"Appendini","year":"2002","journal-title":"Innov. Food Sci. Emerg. Technol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib3d","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1016\/j.tifs.2013.08.001","volume":"33","author":"Sung","year":"2013","journal-title":"Trends Food Sci. Technol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib4a","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1177\/0040517507082332","volume":"78","author":"Gao","year":"2008","journal-title":"Text. Res. J."},{"key":"10.1016\/j.ejmech.2017.01.038_bib4b","doi-asserted-by":"crossref","first-page":"1721","DOI":"10.1177\/0040517510363193","volume":"80","author":"Simoncic","year":"2010","journal-title":"Text. Res. J."},{"key":"10.1016\/j.ejmech.2017.01.038_bib5a","series-title":"Review on Antimicrobial Resistance","year":"2016"},{"key":"10.1016\/j.ejmech.2017.01.038_bib5b","series-title":"Antimicrobial Resistance Global Report on Surveillance","year":"2014"},{"key":"10.1016\/j.ejmech.2017.01.038_bib5c","doi-asserted-by":"crossref","first-page":"1064","DOI":"10.1126\/science.257.5073.1064","volume":"257","author":"Neu","year":"1992","journal-title":"Science"},{"key":"10.1016\/j.ejmech.2017.01.038_bib5d","first-page":"1","volume":"3","author":"Landers","year":"2012","journal-title":"Public Health Rep."},{"key":"10.1016\/j.ejmech.2017.01.038_bib6","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/S1473-3099(06)70689-2","volume":"7","author":"Bradley","year":"2007","journal-title":"Lancet Infect. Dis."},{"key":"10.1016\/j.ejmech.2017.01.038_bib7a","doi-asserted-by":"crossref","first-page":"10706","DOI":"10.1002\/anie.201209979","volume":"52","author":"O'Connell","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"10.1016\/j.ejmech.2017.01.038_bib7b","first-page":"12","author":"Basetti","year":"2013","journal-title":"Ann. Clin. Microbiol. Antimicrob."},{"key":"10.1016\/j.ejmech.2017.01.038_bib7c","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1038\/ja.2013.49","volume":"67","author":"Walsh","year":"2014","journal-title":"J.\u00a0Antibiot."},{"key":"10.1016\/j.ejmech.2017.01.038_bib8a","doi-asserted-by":"crossref","first-page":"321","DOI":"10.1038\/241321a0","volume":"241","author":"Freese","year":"1973","journal-title":"Nature"},{"key":"10.1016\/j.ejmech.2017.01.038_bib8b","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1016\/0168-1605(95)00047-X","volume":"29","author":"Verhaegh","year":"1996","journal-title":"Int. J. Food Microbiol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib9","first-page":"355","volume":"8","author":"Kato","year":"1975","journal-title":"J.\u00a0Antibacter. Antifung. Agents (Jpn)"},{"key":"10.1016\/j.ejmech.2017.01.038_bib10","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1111\/j.1365-2672.1996.tb03276.x","volume":"81","author":"Monk","year":"1996","journal-title":"J.\u00a0Appl. Bacteriol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib11","doi-asserted-by":"crossref","first-page":"1029","DOI":"10.1016\/j.carres.2004.01.007","volume":"339","author":"Devulapalle","year":"2004","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.ejmech.2017.01.038_bib12","doi-asserted-by":"crossref","first-page":"391","DOI":"10.1016\/j.enzmictec.2004.02.009","volume":"36","author":"Ferrer","year":"2005","journal-title":"Enzyme Microb. Technol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib13a","doi-asserted-by":"crossref","first-page":"2557","DOI":"10.1016\/j.carres.2008.07.012","volume":"343","author":"Smith","year":"2008","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.ejmech.2017.01.038_bib13b","first-page":"2152","volume":"108","author":"Nobmann","year":"2010","journal-title":"J.\u00a0Appl. Microbiol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib14","doi-asserted-by":"crossref","first-page":"440","DOI":"10.1016\/j.ijfoodmicro.2008.10.008","volume":"128","author":"Nobmann","year":"2009","journal-title":"Int. J. Food Microbiol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib15a","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1016\/S0304-4157(00)00010-1","volume":"1508","author":"le Maire","year":"2000","journal-title":"Biochim. Biophys. Acta."},{"key":"10.1016\/j.ejmech.2017.01.038_bib15b","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/j.colsurfa.2005.10.053","article-title":"Colloids surf","volume":"277","author":"Piao","year":"2006","journal-title":"A\u00a0physicochem. Eng. Asp."},{"key":"10.1016\/j.ejmech.2017.01.038_bib16a","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1016\/S0378-5173(98)00345-7","volume":"177","author":"Jones","year":"1999","journal-title":"Int. J. Pharm."},{"key":"10.1016\/j.ejmech.2017.01.038_bib16b","doi-asserted-by":"crossref","first-page":"7307","DOI":"10.1021\/la904194a","volume":"26","author":"Ahyayauch","year":"2010","journal-title":"Langmuir"},{"key":"10.1016\/j.ejmech.2017.01.038_bib17","doi-asserted-by":"crossref","first-page":"2668","DOI":"10.1128\/JB.182.9.2668-2671.2000","volume":"182","author":"Ruzin","year":"2000","journal-title":"J.\u00a0Bacteriol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib18","doi-asserted-by":"crossref","first-page":"8115","DOI":"10.1016\/S0021-9258(17)39701-6","volume":"259","author":"Ved","year":"1984","journal-title":"J.\u00a0Biol. Chem."},{"key":"10.1016\/j.ejmech.2017.01.038_bib19","doi-asserted-by":"crossref","first-page":"3061","DOI":"10.1016\/S0040-4020(01)92248-3","volume":"48","author":"Miethchen","year":"1992","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2017.01.038_bib20a","doi-asserted-by":"crossref","first-page":"50653","DOI":"10.1039\/C4RA09350J","volume":"4","author":"Gozlan","year":"2014","journal-title":"RSC Adv."},{"key":"10.1016\/j.ejmech.2017.01.038_bib20b","doi-asserted-by":"crossref","first-page":"1994","DOI":"10.1039\/C5GC02131F","volume":"18","author":"Gozlan","year":"2016","journal-title":"Green Chem."},{"key":"10.1016\/j.ejmech.2017.01.038_bib21","unstructured":"These results were first patented: (a) C. Gozlan, N. Duguet, M. Lemaire, M.-C. Duclos, O. Dumitrescu, G. Lina, A. Redl, Fr. Demande (2016) FR 3030279; (b) C. Gozlan, D. Belmessieri M.-C. Duclos, N. Duguet, M. Lemaire, G. Lina, O. Dumitrescu, A. Redl, PCT Int. Appl. (2016) WO 2016098046."},{"key":"10.1016\/j.ejmech.2017.01.038_bib22","unstructured":"See supporting information for calculations of green metrics."},{"key":"10.1016\/j.ejmech.2017.01.038_bib23","series-title":"Green Chemistry: Theory and Practice","author":"Anastas","year":"1998"},{"key":"10.1016\/j.ejmech.2017.01.038_bib24","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1039\/9781849739986-00051","volume":"40","author":"Molinier","year":"2014","journal-title":"Carbohydr. Chem."},{"key":"10.1016\/j.ejmech.2017.01.038_bib25","doi-asserted-by":"crossref","first-page":"164","DOI":"10.1016\/j.jcis.2010.11.063","volume":"355","author":"Cornella","year":"2011","journal-title":"J.\u00a0Colloid Interf. Sci."},{"key":"10.1016\/j.ejmech.2017.01.038_bib26a","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1016\/j.jcis.2012.02.006","volume":"374","author":"Rauwel","year":"2012","journal-title":"J.\u00a0Colloid Interface Sci."},{"key":"10.1016\/j.ejmech.2017.01.038_bib26b","series-title":"Solution Chemistry of Surfactants","first-page":"337","article-title":"Mixed micelle solutions","author":"Rubingh","year":"1979"},{"key":"10.1016\/j.ejmech.2017.01.038_bib27","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/S0008-6215(98)00207-9","volume":"311","author":"Vanbaelinghem","year":"1998","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.ejmech.2017.01.038_bib28","doi-asserted-by":"crossref","first-page":"683","DOI":"10.1007\/s11743-013-1529-2","volume":"17","author":"Ariffin","year":"2014","journal-title":"J.\u00a0Surfactants Deterg."},{"key":"10.1016\/j.ejmech.2017.01.038_bib29","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1021\/la010727g","volume":"18","author":"Ferrer","year":"2002","journal-title":"Langmuir"},{"key":"10.1016\/j.ejmech.2017.01.038_bib30","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1246\/bcsj.34.237","volume":"34","author":"Shinoda","year":"1961","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"10.1016\/j.ejmech.2017.01.038_bib31","doi-asserted-by":"crossref","first-page":"487","DOI":"10.1021\/jp109545v","volume":"115","author":"Abel","year":"2011","journal-title":"J.\u00a0Phys. Chem. B"},{"key":"10.1016\/j.ejmech.2017.01.038_bib32","unstructured":"Minimum Inhibitory Concentration (MIC) values are defined as the lowest concentration of compound that shows no cell growth for all the replicates compared to the negative control after 18h."},{"key":"10.1016\/j.ejmech.2017.01.038_bib33","unstructured":"See supporting information for experimental details and the MIC values obtained against gram-negative strains."},{"key":"10.1016\/j.ejmech.2017.01.038_bib34","unstructured":"The Minimum Bactericidal Concentration (MBC) was determined by diluting the well below the MIC. The enumeration was then carried out after plating for 18 h. The MBC corresponds to the lowest concentration of antimicrobial agent required to decrease the initial bacterial inoculum by at least 99.9%."},{"key":"10.1016\/j.ejmech.2017.01.038_bib35","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1016\/S0304-4157(00)00012-5","volume":"1508","author":"Schereier","year":"2000","journal-title":"Biochimi. Biophys. Acta"},{"key":"10.1016\/j.ejmech.2017.01.038_bib36","unstructured":"See supporting information for experimental details."},{"key":"10.1016\/j.ejmech.2017.01.038_bib37","doi-asserted-by":"crossref","first-page":"17531","DOI":"10.1021\/jp502819s","volume":"118","author":"Garc\u00eda-Muelas","year":"2014","journal-title":"J.\u00a0Phys. Chem. C"},{"key":"10.1016\/j.ejmech.2017.01.038_bib37a","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1111\/j.1749-6632.2012.06819.x","volume":"1277","author":"Bayer","year":"2013","journal-title":"Ann. N. Y. Acad. Sci."},{"key":"10.1016\/j.ejmech.2017.01.038_bib37b","doi-asserted-by":"crossref","first-page":"831","DOI":"10.1007\/s10096-008-0692-2","volume":"28","author":"Cunha","year":"2009","journal-title":"Eur. J. Clin. Microbiol. Infect. Dis."},{"key":"10.1016\/j.ejmech.2017.01.038_bib37c","doi-asserted-by":"crossref","first-page":"269","DOI":"10.1128\/AAC.00719-07","volume":"52","author":"Jones","year":"2008","journal-title":"Antimicrob. Agents Chemother."},{"key":"10.1016\/j.ejmech.2017.01.038_bib37d","doi-asserted-by":"crossref","first-page":"5285","DOI":"10.1128\/JCM.43.10.5285-5287.2005","volume":"43","author":"Hayden","year":"2005","journal-title":"J.\u00a0Clin. Microbiol."},{"key":"10.1016\/j.ejmech.2017.01.038_bib37e","doi-asserted-by":"crossref","first-page":"1058","DOI":"10.1086\/428616","volume":"40","author":"Mangili","year":"2005","journal-title":"Clin. Infect. Dis."},{"key":"10.1016\/j.ejmech.2017.01.038_bib39","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1016\/S0021-9673(00)87968-6","volume":"208","author":"Cheetham","year":"1981","journal-title":"J.\u00a0Chromarogr"},{"key":"10.1016\/j.ejmech.2017.01.038_bib40","doi-asserted-by":"crossref","first-page":"11414","DOI":"10.1021\/ja0518575","volume":"127","author":"Carcabal","year":"2005","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"10.1016\/j.ejmech.2017.01.038_bib41","doi-asserted-by":"crossref","first-page":"2097","DOI":"10.1016\/j.carres.2007.05.011","volume":"342","author":"Kr\u00e4utler","year":"2007","journal-title":"Carbohydr. Res."},{"key":"10.1016\/j.ejmech.2017.01.038_bib42","doi-asserted-by":"crossref","first-page":"1490","DOI":"10.1039\/P19900001490","volume":"1","author":"Angibeaud","year":"1990","journal-title":"J.\u00a0Chem. Soc. Perkin Trans."}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S022352341730048X?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S022352341730048X?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2022,7,22]],"date-time":"2022-07-22T18:20:50Z","timestamp":1658514050000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S022352341730048X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,3]]},"references-count":61,"alternative-id":["S022352341730048X"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2017.01.038","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2017,3]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2017.01.038","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2017 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}]}}