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This process typically proceeds along a complex SN1-SN2 mechanistic continuum. In solution, the key contributions to these mechanisms are difficult to determine due to influence by structural and environmental variables, such as solvents, counterions or temperature. To isolate the intrinsic factors driving steroselectivity in glycosylations, we investigate the reactions for the monosaccharide galactose in the gas phase. We perform ion\u2013molecule galactosylation reactions in complete isolation inside an ion trap of a mass spectrometer and directly probe the stereochemistry of the formed products using mass-resolved ultraviolet cold ion spectroscopy. The results show that \u03b1-selectivity is significantly weaker in the gas phase than in solution, and that the product stereochemistry might be influenced by the nucleophile\u2019s electron density rather than its overall nucleophilic strength.<\/jats:p>","DOI":"10.1021\/jacs.6c09131","type":"journal-article","created":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T19:02:07Z","timestamp":1785956527000},"page":"34045-34050","source":"Crossref","is-referenced-by-count":0,"title":["Stereoselectivity of\nGalactosylation Reactions\n                    <i>In Vacuo<\/i>"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0253-3463","authenticated-orcid":true,"given":"Chun-Wei","family":"Chang","sequence":"first","affiliation":[{"name":"Freie Universita\u0308t Berlin , , Altensteinstra\u00dfe 23A , ,","place":["Berlin, Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 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Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 14195"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2894-3126","authenticated-orcid":true,"given":"Jacob S.","family":"Jordan","sequence":"additional","affiliation":[{"name":"Freie Universita\u0308t Berlin , , Altensteinstra\u00dfe 23A , ,","place":["Berlin, Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 14195"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana","family":"Zidar","sequence":"additional","affiliation":[{"name":"Freie Universita\u0308t Berlin , , Altensteinstra\u00dfe 23A , ,","place":["Berlin, Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 14195"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ariane R.","family":"Wieseke","sequence":"additional","affiliation":[{"name":"Freie Universita\u0308t Berlin , , Altensteinstra\u00dfe 23A , ,","place":["Berlin, Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 14195"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9107-2282","authenticated-orcid":true,"given":"Kim","family":"Greis","sequence":"additional","affiliation":[{"name":"Freie Universita\u0308t Berlin , , Altensteinstra\u00dfe 23A , ,","place":["Berlin, Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 14195"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gae\u0308l M.","family":"Vos","sequence":"additional","affiliation":[{"name":"Freie Universita\u0308t Berlin , , Altensteinstra\u00dfe 23A , ,","place":["Berlin, Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 14195"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Go\u0308tze","sequence":"additional","affiliation":[{"name":"Freie Universita\u0308t Berlin , , Altensteinstra\u00dfe 23A , ,","place":["Berlin, Germany, 14195"]},{"name":"Fritz Haber Institute of the Max Planck Society , , Faradayweg 4-6 , ,","place":["Berlin, Germany, 14195"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8867-3434","authenticated-orcid":true,"given":"Oleg","family":"Boyarkin","sequence":"additional","affiliation":[{"name":"E\u0301cole Polytechnique Fe\u0301de\u0301rale de Lausanne , , Station 6 , ,","place":["Lausanne, Switzerland, CH-1015"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8054-4718","authenticated-orcid":true,"given":"Kevin","family":"Pagel","sequence":"additional","affiliation":[{"name":"Freie 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Chem."},{"key":"2026081910245899200_cit41","doi-asserted-by":"publisher","first-page":"1054","DOI":"10.1021\/acs.jpcb.5c07574","article-title":"Exploring\nthe Mutarotation Mechanism of Glucose in Solution Using Deep Learning\nPotential","volume":"130","author":"Cui","year":"2026","journal-title":"J. Phys. Chem. B"},{"key":"2026081910245899200_cit42","doi-asserted-by":"publisher","first-page":"5948","DOI":"10.1021\/jacs.0c00264","article-title":"How General Is Anomeric\nRetention during Collision-Induced\nDissociation of Glycans?","volume":"142","author":"Pellegrinelli","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"2026081910245899200_cit43","doi-asserted-by":"publisher","first-page":"1905","DOI":"10.1002\/cphc.202000473","article-title":"The Impact of Leaving Group Anomericity on the Structure of Glycosyl\nCations of Protected Galactosides","volume":"21","author":"Greis","year":"2020","journal-title":"ChemPhysChem"},{"key":"2026081910245899200_cit44","doi-asserted-by":"publisher","first-page":"1867","DOI":"10.1039\/C6SC04638J","article-title":"The Influence of Acceptor Nucleophilicity\non the Glycosylation Reaction Mechanism","volume":"8","author":"van der Vorm","year":"2017","journal-title":"Chem.\nSci."},{"key":"2026081910245899200_cit45","doi-asserted-by":"publisher","first-page":"4688","DOI":"10.1039\/C8CS00369F","article-title":"Acceptor Reactivity in Glycosylation Reactions","volume":"48","author":"van der Vorm","year":"2019","journal-title":"Chem. Soc. 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