Regioselective monodeprotection of peracetylated carbohydrates.

Abstract

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.

• Authors: Marco Filice, Jose M Guisan, Marco Terreni, Jose M Palomo
• Journal: Nature protocols (Nat Protoc) Vol. 7 Issue 10 Pg. 1783-96 (Oct 2012) ISSN: 1750-2799 [Electronic] England
• PMID: 22955694 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Carbohydrates
• Oligosaccharides

Topics

• Carbohydrates (chemical synthesis, chemistry)
• Chemistry (methods)
• Glycosylation
• Oligosaccharides (chemical synthesis, chemistry)