Chemical Communications 2013-04-25

Synthesis of L-hexoses and their related biomolecules.

Medel Manuel L Zulueta, Yong-Qing Zhong, Shang-Cheng Hung

Index: Chem. Commun. (Camb.) 49(32) , 3275-87, (2013)

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Abstract

Carbohydrates either conjugated or as free entities are major players in numerous biological processes. The desire to comprehend the nature of their functions and further develop therapeutic and diagnostic applications has fuelled the recent upsurge in the glycoscience field. Mainly accessed through chemical synthesis, homogeneous and well-defined sugar constructs are on high demand for structure-activity evaluation. Although the d-sugars, particularly the d-hexoses, have dominated the carbohydrate landscape, L-hexoses also attracted attention because they are known components of important polysaccharides, antibiotics, and other natural products. Nonetheless, the L-hexose-based materials needed for making building blocks for sugar assemblies are rare and are usually expensive if commercially available. Thus, intense efforts were focused on the development of innovative and reliable methods for the acquisition of L-hexoses and their derivatives. This review outlines several efficient and cost-effective routes for the chemical syntheses of L-hexoses, particularly focusing on approaches that utilize commercially abundant sugars as starting materials. A sampling of the applications of the generated L-hexoses in preparing biologically relevant compounds is also provided.