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It was shown that <jats:italic>Bacillus circulans<\/jats:italic> 251 cyclodextrin glucanotransferase (CGTase, EC 2.1.4.19) can efficiently couple an \u03b1\u2010<jats:sc>L<\/jats:sc>\u2010rhamnosyl acceptor to a maltodextrin molecule with an \u03b1\u2010(1\u21924) linkage, albeit in mixture with the \u03b1\u2010(1\u21923) regioisomer, thus giving two glucosylated acceptors in a single reaction. Optimisation of the CGTase coupling reaction with \u03b2\u2010cyclodextrin as the donor substrate and methyl or allyl \u03b1\u2010<jats:sc>L<\/jats:sc>\u2010rhamnopyranoside as acceptors resulted in good conversion yields (42\u201370\u2009%) with adjustable glycosylation regioselectivity. Moreover, the efficient chemical conversion of the products of CGTase\u2010mediated <jats:italic>cis<\/jats:italic>\u2010glucosylation into protected building blocks (previously used in the synthesis of O\u2010antigen fragments of several <jats:italic>Shigella flexneri<\/jats:italic> serotypes) was substantiated. These novel chemoenzymatic strategies towards useful, convenient intermediates in the synthesis of <jats:italic>S. flexneri<\/jats:italic> serotypes 2a and 3a oligosaccharides might find applications in developments towards synthetic carbohydrate\u2010based vaccine candidates against bacillary dysentery.<\/jats:p>","DOI":"10.1002\/cbic.201300597","type":"journal-article","created":{"date-parts":[[2013,12,20]],"date-time":"2013-12-20T13:24:36Z","timestamp":1387545876000},"page":"293-300","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["CGTase\u2010Catalysed <i>cis<\/i>\u2010Glucosylation of <scp>L<\/scp>\u2010Rhamnosides for the Preparation of <i>Shigella flexneri<\/i> 2a and 3a Haptens"],"prefix":"10.1002","volume":"15","author":[{"given":"Carole","family":"Urbach","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sami","family":"Halila","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Catherine","family":"Guerreiro","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hugues","family":"Driguez","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Laurence A.","family":"Mulard","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sylvie","family":"Armand","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,12,20]]},"reference":[{"key":"e_1_2_6_1_2","volume-title":"Essentials of Glycobiology","year":"2009"},{"key":"e_1_2_6_2_2","unstructured":"\u00a0"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.3109\/08923970903292663"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100296"},{"key":"e_1_2_6_5_2","unstructured":"\u00a0"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035125b"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400903"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802127z"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.4049\/jimmunol.176.3.1686"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M510172200"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300180"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.4049\/jimmunol.0803141"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrmicro1662"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1574-695X.2012.01000.x"},{"key":"e_1_2_6_15_2","unstructured":"\u00a0"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/cc9960002541"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr950031q"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0959-440X(97)80074-7"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9936520"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200300692"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200505070"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2006.12.017"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja900183h"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja306845b"},{"key":"e_1_2_6_25_2","unstructured":"\u00a0"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.56.1386"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.58.517"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1271\/bbb.60.1176"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi000340x"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00180a008"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00010a028"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/prot.10516"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1432-1327.2000.01353.x"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1046\/j.1432-1327.2000.01031.x"},{"key":"e_1_2_6_35_2","unstructured":"\u00a0"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1080\/07328300008544123"},{"key":"e_1_2_6_37_2","first-page":"254","volume":"11","author":"Bakinovskii L. 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