Title |
Regioselective monodeprotection of peracetylated carbohydrates
|
---|---|
Published in |
Nature Protocols, September 2012
|
DOI | 10.1038/nprot.2012.098 |
Pubmed ID | |
Authors |
Marco Filice, Jose M Guisan, Marco Terreni, Jose M Palomo |
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. |
Mendeley readers
Geographical breakdown
Country | Count | As % |
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Unknown | 62 | 100% |
Demographic breakdown
Readers by professional status | Count | As % |
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Student > Ph. D. Student | 13 | 21% |
Student > Master | 11 | 18% |
Researcher | 9 | 15% |
Student > Doctoral Student | 7 | 11% |
Student > Bachelor | 6 | 10% |
Other | 5 | 8% |
Unknown | 11 | 18% |
Readers by discipline | Count | As % |
---|---|---|
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Agricultural and Biological Sciences | 4 | 6% |
Biochemistry, Genetics and Molecular Biology | 3 | 5% |
Unspecified | 1 | 2% |
Chemical Engineering | 1 | 2% |
Other | 2 | 3% |
Unknown | 13 | 21% |