Practical synthesis of d-[1-13C]mannose, l-[1-13C] and l-[6-13C]fucose

The chemical synthesis of 13C-labeled mannose and fucose is important for the preparation of molecular probes used in the conformational study of the oligosaccharide portions of glycoproteins. A new method for the synthesis of the title [1-13C]-labeled compounds via the corresponding olefin compounds, which are in turn derived from d-mannitol or l-arabinose by efficient introduction of 13C, by the Wittig reaction using Ph3P13CH3I and n-BuLi, is described. The introduction of 13CH3I to produce the [1-13C]- and [6-13C]-labeled compounds was accomplished in 62%, 56%, and 71% yields, respectively. All mannose and fucose protons, from H-1 to H-6, were observed by the HMQC-TOCSY technique using 1:1 mixtures of [1-13C]- and [6-13C]-labeled compounds.