Strengthening an Intramolecular Non‐Classical Hydrogen Bond to Get in Shape for Binding DOI Creative Commons
Norbert Varga, Martin Smieško, Xiaohua Jiang

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Июль 27, 2024

Abstract In this research article, we report on the strengthening of a non‐classical hydrogen bond (C−H⋅⋅⋅O) by introducing electron withdrawing groups at carbon atom. The approach is demonstrated example derivatives physiological E‐selectin ligand sialyl Lewis x ( 1 , sLe ). Its affinity mainly due to beneficial entropy term, which predominantly caused pre‐organization in its binding conformation. We have shown, that among elements responsible for pre‐organization, stabilization between H−C5 l ‐fucose and ring oxygen O5 neighboring d ‐galactose moiety essential yields 7.4 kJ mol −1 . This effect could be further strengthened replacing 6,6,6‐trifluoro‐ leading an improved H‐bond 14.9 i.e., bioactive For series glycomimetics ), outcome confirmed high field NMR‐shifts Fuc X‐ray diffraction analysis co‐crystallized with as well isothermal titration calorimetry. Furthermore, electron‐withdrawing character CF 3 ‐group beneficially influences pharmacokinetic properties mimetics. Thus, acid‐stability, prerequisite gastrointestinal stability, substantially improved.

Язык: Английский

NMR investigations of glycan conformation, dynamics, and interactions DOI
Jesús Angulo, Ana Ardá, Sara Bertuzzi

и другие.

Progress in Nuclear Magnetic Resonance Spectroscopy, Год журнала: 2024, Номер 144-145, С. 97 - 152

Опубликована: Окт. 12, 2024

Язык: Английский

Процитировано

4
Strengthening an Intramolecular Non‐Classical Hydrogen Bond to Get in Shape for Binding DOI Creative Commons
Norbert Varga, Martin Smieško, Xiaohua Jiang

и другие.

Angewandte Chemie, Год журнала: 2024, Номер 136(42)

Опубликована: Июль 27, 2024

Abstract In this research article, we report on the strengthening of a non‐classical hydrogen bond (C−H⋅⋅⋅O) by introducing electron withdrawing groups at carbon atom. The approach is demonstrated example derivatives physiological E‐selectin ligand sialyl Lewis x ( 1 , sLe ). Its affinity mainly due to beneficial entropy term, which predominantly caused pre‐organization in its binding conformation. We have shown, that among elements responsible for pre‐organization, stabilization between H−C5 l ‐fucose and ring oxygen O5 neighboring d ‐galactose moiety essential yields 7.4 kJ mol −1 . This effect could be further strengthened replacing 6,6,6‐trifluoro‐ leading an improved H‐bond 14.9 i.e., bioactive For series glycomimetics ), outcome confirmed high field NMR‐shifts Fuc X‐ray diffraction analysis co‐crystallized with as well isothermal titration calorimetry. Furthermore, electron‐withdrawing character CF 3 ‐group beneficially influences pharmacokinetic properties mimetics. Thus, acid‐stability, prerequisite gastrointestinal stability, substantially improved.

Язык: Английский

Процитировано

3
Nanoarchitectonics of cello-oligosaccharides: A route toward artificial nanocelluloses DOI Creative Commons
Yuuki Hata, Takeshi Serizawa

Advances in Colloid and Interface Science, Год журнала: 2024, Номер 336, С. 103361 - 103361

Опубликована: Ноя. 29, 2024

Язык: Английский

Процитировано

3
A glycan foldamer that uses carbohydrate–aromatic interactions to perform catalysis DOI Creative Commons
Kaimeng Liu, Martina Delbianco

Nature Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 26, 2025

Язык: Английский

Процитировано

0
Controlling Glycan Folding with Ionic Functional Groups DOI Creative Commons

Nishu Yadav,

Ana Poveda,

Yadiel Vázquez Mena

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 24, 2025

Glycans are intrinsically flexible molecules that can adopt many conformations. These often carry ionic functional groups influence glycan's conformational preferences, dynamics, and aggregation tendencies. Inspired by these mechanisms, we have engineered a glycan sequence whose secondary structure be precisely manipulated using groups. We strategically incorporated substituents into adopting hairpin conformation. Complementary stabilized the closed conformers, while repulsions shifted populations toward open forms. External stimuli, such as pH variations or enzyme addition, enabled us to dynamically control hairpin's opening closing. Additionally, changes in protonation states led aggregation, suggesting opportunities for creation of responsive glycan-based materials.

Язык: Английский

Процитировано

0
The synergy of experimental and computational approaches for visualizing glycoprotein dynamics: Exploring order within the apparent disorder of glycan conformational ensembles DOI Creative Commons
Koichi Kato, Saeko Yanaka, Takumi Yamaguchi

и другие.

Current Opinion in Structural Biology, Год журнала: 2025, Номер 92, С. 103049 - 103049

Опубликована: Апрель 29, 2025

Understanding the dynamic behavior of glycoproteins is crucial for deciphering their biological roles. This review explores synergistic use experimental and computational methods to address this complex challenge. Glycans, with inherent flexibility structural diversity, pose significant obstacles traditional analysis. Innovative techniques offer valuable snapshots glycan conformations, but often lack context a physiological environment. Computational simulations provide atomic-level detail explore full range motions, require extensive resources validation. Integrating these approaches, by using data refine validate models, essential accurately capturing interplay between glycans proteins. combined strategy promises unlock deeper understanding glycoprotein function inform design novel therapeutics.

Язык: Английский

Процитировано

0
Strengthening an Intramolecular Non‐Classical Hydrogen Bond to Get in Shape for Binding DOI Creative Commons
Norbert Varga, Martin Smieško, Xiaohua Jiang

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Июль 27, 2024

Abstract In this research article, we report on the strengthening of a non‐classical hydrogen bond (C−H⋅⋅⋅O) by introducing electron withdrawing groups at carbon atom. The approach is demonstrated example derivatives physiological E‐selectin ligand sialyl Lewis x ( 1 , sLe ). Its affinity mainly due to beneficial entropy term, which predominantly caused pre‐organization in its binding conformation. We have shown, that among elements responsible for pre‐organization, stabilization between H−C5 l ‐fucose and ring oxygen O5 neighboring d ‐galactose moiety essential yields 7.4 kJ mol −1 . This effect could be further strengthened replacing 6,6,6‐trifluoro‐ leading an improved H‐bond 14.9 i.e., bioactive For series glycomimetics ), outcome confirmed high field NMR‐shifts Fuc X‐ray diffraction analysis co‐crystallized with as well isothermal titration calorimetry. Furthermore, electron‐withdrawing character CF 3 ‐group beneficially influences pharmacokinetic properties mimetics. Thus, acid‐stability, prerequisite gastrointestinal stability, substantially improved.

Язык: Английский

Процитировано

1