This protocol describes the regioselective deprotection of single hydroxyls in peracetylated monosaccharides and disaccharides by enzymatic or chemoenzymatic strategies. The introduction of a one-pot enzymatic step by using immobilized biocatalysts obviates the requirement to carry out tedious workups and time-consuming purifications. By using this straightforward protocol, different per-O-acetylated glycopyranosides (mono- or disaccharides, 1-substituted or glycals) can be transformed into a whole set of differentially monodeprotected 1-alcohols, 3-alcohols, 4-alcohols and 6-alcohols in high yields. These tailor-made glycosyl acceptors can then be used for stereoselective glycosylation for oligosaccharide and glycoderivative synthesis. They have been successfully used as building blocks to synthesize tailor-made di- and trisaccharides involved in the structure of lacto-N-neo-tetraose and precursors of the tumor-associated carbohydrate antigen T and the antitumoral drug peracetylated β-naphtyl-lactosamine. We are able to prepare a purified monoprotected carbohydrate in between 1 and 4 d. With this protocol, the small library of monodeprotected products can be synthesized in 1–2 weeks.
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This work was supported by The Spanish National Research Council (CSIC) and the Spanish Ministry of Science. We acknowledge Á. Berenguer (Instituto Universitario de Materiales, Universidad de Alicante) for his help during the writing of this paper.
The authors declare no competing financial interests.
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Filice, M., Guisan, J., Terreni, M. et al. Regioselective monodeprotection of peracetylated carbohydrates. Nat Protoc 7, 1783–1796 (2012). https://doi.org/10.1038/nprot.2012.098
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