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Zinc ion complexation with specific glycosyl donors induces conformational changes, slightly increasing their reactivity. This finding is crucial for understanding carbohydrate chemistry and developing new synthetic strategies.

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Area of Science:

  • Carbohydrate Chemistry
  • Organometallic Chemistry
  • Supramolecular Chemistry

Background:

  • Glycosyl donors are key building blocks in carbohydrate synthesis.
  • The coordination of metal ions to functionalized glycosyl donors can alter their properties.
  • 2,2'-bipyridine moieties are common ligands for metal ions.

Purpose of the Study:

  • To investigate the conformational changes of glycosyl donors upon Zn2+ complexation.
  • To determine the effect of these conformational changes on glycosyl donor reactivity.
  • To elucidate the role of metal-ion-induced conformation in glycosylation reactions.

Main Methods:

  • Synthesis of glycosyl donors functionalized with 2,2'-bipyridine.
  • Formation of 1:1 complexes with Zn2+ ions.
  • Analysis of complex conformations using NMR spectroscopy.
  • Glycosylation reactions performed in the presence and absence of Zn2+.
  • Competition experiments to compare reactivity.

Main Results:

  • Glycosyl donors with 2,2'-bipyridine moieties at specific positions (3-OH/6-OH or 2-OH/4-OH) formed 1:1 complexes with Zn2+.
  • Complexation induced a conformational change in the pyranoside ring to axial-rich skew boat conformations.
  • Glycosylation reactions showed a slight decrease in reactivity upon Zn2+ binding.
  • Competition experiments revealed that the binding-induced conformational change slightly increased reactivity compared to a non-conformational-changing analogue.

Conclusions:

  • Zn2+ complexation significantly alters the conformation of specific glycosyl donors.
  • The conformational change induced by Zn2+ binding has a subtle but measurable impact on glycosyl donor reactivity.
  • Understanding these metal-ion-mediated conformational effects is important for controlling glycosylation outcomes.