Redundant ¹⁵N-Mediated <i>J</i>-Couplings Reveal an Aglycone Conformation in <i>N</i>-Phenyl Glycosylamines.

ABSTRACT: Prediction of the conformation of novel N-glycomimetics is a crucial step in their rational design for drug discovery and glycobiology. We investigated the applicability of redundant ¹⁵N-mediated J-couplings for predicting the aniline aglycone conformation in ¹⁵N-labeled N-phenyl glycosylamines derived from d-glucose (d-Glc), d-mannose (d-Man), d-xylose (d-Xyl), and d-lyxose (d-Lyx). The compounds were prepared directly in an NMR tube by reacting free sugar with ¹⁵N-labeled aniline, achieving >90% conversion. The rate of N-phenyl glycosylamine formation depended on the concentration of an open-chain form of the sugar in the solution. In the closed form, the anilino substituent preferred equatorial orientation, which dictated the

SUBMITTER: Habanova N 

PROVIDER: S-EPMC12624841 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature