van Hengst Jacob M A, Hellemons Rik J C, Remmerswaal Wouter A, van de Vrande Koen N A, Hansen Thomas, van der Vorm Stefan, Overkleeft Hermen S, van der Marel Gijsbert A, Codée Jeroen D C
Leiden University, Leiden Institute of Chemistry Einsteinweg 55 2333 CC Leiden The Netherlands
Department of Theoretical Chemistry, Amsterdam Institute of Molecular and Life Sciences (AIMMS), Amsterdam Center for Multiscale Modeling (ACMM), Vrije Universiteit Amsterdam De Boelelaan 1083 1081 HV Amsterdam The Netherlands.
Chem Sci. 2023 Jan 13;14(6):1532-1542. doi: 10.1039/d2sc06139b. eCollection 2023 Feb 8.
The reactivity of the acceptor alcohol can have a tremendous influence on the outcome of a glycosylation reaction, both in terms of yield and stereoselectivity. Through a systematic survey of 67 acceptor alcohols in glycosylation reactions with two glucosyl donors we here reveal how the reactivity of a carbohydrate acceptor depends on its configuration and substitution pattern. The study shows how the functional groups flanking the acceptor alcohol influence the reactivity of the alcohol and show that both the nature and relative orientation play an essential role. The empiric acceptor reactivity guidelines revealed here will aid in the rational optimization of glycosylation reactions and be an important tool in the assembly of oligosaccharides.
受体醇的反应性对糖基化反应的结果，无论是产率还是立体选择性，都可能产生巨大影响。通过对67种受体醇与两种葡萄糖基供体进行糖基化反应的系统研究，我们在此揭示了碳水化合物受体的反应性如何取决于其构型和取代模式。该研究表明了受体醇两侧的官能团如何影响醇的反应性，并表明官能团的性质和相对取向都起着至关重要的作用。此处揭示的经验性受体反应性指导原则将有助于合理优化糖基化反应，并成为组装寡糖的重要工具。
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