{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T07:17:24Z","timestamp":1788333444988,"version":"build-2803163510"},"reference-count":47,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T00:00:00Z","timestamp":1788307200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    The difructose dianhydride I synthase\/hydrolase  catalyzes the reversible transformation of inulobiose into difructose dianhydride I, a component of caramel. The proposed reaction mechanism of such a transformation consists of a glycosylation step followed by a cyclization to yield the dianhydride from the disaccharide. Here, we make use of extensive hybrid QM\/MM metadynamics studies to shed light on the molecular basis of it. Our simulations show that the global reaction for the transformation of inulobiose by  is slightly exergonic in good agreement with the experimental data. Furthermore, we observe that the glycosylation step is the rate\u2010limiting step. Interestingly, our work shows that the \u20131 sugar of inulobiose changes from an initial\n                    <jats:italic>E<\/jats:italic>\n                    conformation into a\n                    <jats:italic>E<\/jats:italic>\n                    puckering via the conformational pathway\n                    <jats:italic>E<\/jats:italic>\n                    <jats:italic>E<\/jats:italic>\n                    \/\n                    <jats:italic>T<\/jats:italic>\n                    <jats:italic>E<\/jats:italic>\n                    <jats:italic>E<\/jats:italic>\n                    . Our calculations highlight that in the cyclization step, the three residues E85, K147, and N226 are essential for the rotation of the +1 sugar in the substrate to facilitate the intramolecular attack of oxygen O1' to the anomeric carbon. Prompted by these results, we expressed and assayed the N226A  variant. Enzyme activity data confirm an important role for N226 during the cyclization step but show that it is dispensable for the hydrolysis step.\n                  <\/jats:p>","DOI":"10.1002\/chem.71544","type":"journal-article","created":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T07:02:26Z","timestamp":1788332546000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["GH172 Difructose Dianhydride I Synthase: A Two\u2010Stepped Journey via Glycosylation and Cyclization Using QM\/MM Metadynamics"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7596-8161","authenticated-orcid":false,"given":"Santiago","family":"Alonso\u2010Gil","sequence":"first","affiliation":[{"name":"Department of Structural and Computational Biology, Max Perutz Labs University of Vienna Vienna Austria"},{"name":"Laboratory of Computer\u2010Aided Molecular Design, Division of Medicinal Chemistry, Otto\u2010Loewi Research Center Medical University of Graz Graz Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1822-7142","authenticated-orcid":false,"given":"Bruno","family":"Di Geronimo","sequence":"additional","affiliation":[{"name":"Laboratory of Computer\u2010Aided Molecular Design, Division of Medicinal Chemistry, Otto\u2010Loewi Research Center Medical University of Graz Graz Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3372-0827","authenticated-orcid":false,"given":"Toma","family":"Kashima","sequence":"additional","affiliation":[{"name":"Department of Biotechnology The University of Tokyo Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5542-2214","authenticated-orcid":false,"given":"Akihiro","family":"Ishiwata","sequence":"additional","affiliation":[{"name":"Pioneering Research Institute RIKEN Wako Saitama Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6932-4802","authenticated-orcid":false,"given":"Katsunori","family":"Tanaka","sequence":"additional","affiliation":[{"name":"Pioneering Research Institute RIKEN Wako Saitama Japan"},{"name":"School of Materials and Chemical Technology, Department of Chemical Science and Engineering Institute of Science Tokyo Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3780-3750","authenticated-orcid":false,"given":"Kiyotaka","family":"Fujita","sequence":"additional","affiliation":[{"name":"Faculty of Agriculture Kagoshima University Kagoshima Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1346-6435","authenticated-orcid":false,"given":"Shinya","family":"Fushinobu","sequence":"additional","affiliation":[{"name":"Department of Biotechnology The University of Tokyo Tokyo Japan"},{"name":"Collaborative Research Institute for Innovative Microbiology The University of Tokyo Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8415-870X","authenticated-orcid":false,"given":"Pedro A.","family":"S\u00e1nchez\u2010Murcia","sequence":"additional","affiliation":[{"name":"Laboratory of Computer\u2010Aided Molecular Design, Division of Medicinal Chemistry, Otto\u2010Loewi Research Center Medical University of Graz Graz Austria"},{"name":"BioTechMed\u2010Graz Graz Austria"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,2]]},"reference":[{"issue":"12","key":"e_1_2_11_2_1","doi-asserted-by":"crossref","first-page":"3266","DOI":"10.1021\/jf204807z","article-title":"Unraveling the Chemical Composition of Caramel","volume":"60","author":"Golon A.","year":"2012","journal-title":"Journal of Agricultural and Food 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