Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

• Vojtěch Hamala,
• Lucie Červenková Šťastná,
• Martin Kurfiřt,
• Petra Cuřínová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

• desolvation penalty associated with binding of hydrophilic natural carbohydrates [8], and (2) create additional contacts with the binding cavity via electrostatic and dipolar interactions with C–F bonds [9][10], new intermolecular hydrogen bonds [11], or rearrangement of hydrogen bond-mediating water

What contributes to an effective mannose recognition domain?

• Christoph P. Sager,
• Deniz Eriş,
• Martin Smieško,
• Rachel Hevey and
• Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

• described, the various approaches explored by nature to optimize selectivity and affinity of carbohydrate–lectin interactions offer interesting therapeutic perspectives for the development of carbohydrate-based drugs. Keywords: carbohydrate–lectin interactions; desolvation penalty; dielectric constant

• overall desolvation penalty is slightly reduced resulting in an overall desolvation cost of ΔG = 34 kJ/mol for both hydroxy groups (Figure 4B). Since carbohydrates in general exhibit a number of adjacent hydroxy groups, their desolvation penalties are difficult to assess but it is most likely that each

• single water molecule coordinated to the calcium ion (calculated as a simple difference of the electronic energies of three molecular species: Edesolv = Ereceptor···water − Ereceptor − Ewater) is approximately 77 kJ/mol [66]. Interestingly, the calculated desolvation penalty per calcium ion is more