Stereo- and regioselective direct multi-deuterium-labeling methods for sugars

Area of Science:

• Carbohydrate Chemistry
• Organic Synthesis
• Isotope Labeling

Background:

• Deuterium-labeled sugars offer advantages in analyzing complex molecules like nucleic acids and glycoproteins.
• Their applications include simplifying NMR spectra and enhancing C-D bond stability for drug synthesis.

Purpose of the Study:

• To establish an efficient and direct method for synthesizing deuterated sugars from non-labeled precursors.
• To enable precise deuterium incorporation for advanced molecular analysis and drug development.

Main Methods:

• Utilized a heterogeneous Ru/C-catalyzed hydrogen-deuterium (H-D) exchange reaction in deuterium oxide (D2O) under a hydrogen atmosphere.
• Employed site-selective protection of hydroxyl groups using acetal-type protecting groups to control deuterium incorporation positions.

Main Results:

• Achieved direct and efficient H-D exchange with perfect chemo- and stereoselectivities.
• Successfully deuterated various pyranosides (e.g., glucose, disaccharides) and furanosides (e.g., ribose, deoxyribose).
• Demonstrated site-selective deuterium labeling by protecting hydroxyl groups, preventing exchange at those positions.

Conclusions:

• The developed method provides a versatile and efficient route to site-specifically deuterated sugars.
• This technique facilitates the use of deuterium-labeled sugars as valuable tools in structural biology and medicinal chemistry.