ArticleNature protocols2012
Regioselective monodeprotection of peracetylated carbohydrates.
Article in Nature protocols, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Effect of glycosylation on the affinity of the MTB protein Ag85B for specific antibodies: towards the design of a dual-acting vaccine against tuberculosis.Biology direct · 2024Article
- Biocatalyzed Synthesis of Glycostructures with Anti-infective Activity.Accounts of chemical research · 2022Review
- Microbial Lipases and Their Potential in the Production of Pharmaceutical Building Blocks.International journal of molecular sciences · 2022Review
- Geranyl Functionalized Materials for Site-Specific Co-Immobilization of Proteins.Molecules (Basel, Switzerland) · 2021Article
- New Advances in Fabrication of Graphene Glyconanomaterials for Application in Therapy and Diagnosis.ACS omega · 2020Review
- Fine Modulation of the Catalytic Properties ofMolecules (Basel, Switzerland) · 2020Article
- Modulation of the Catalytic Properties of Lipase B fromPolymers · 2018Article
- Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate.Molecules (Basel, Switzerland) · 2016Article
- Synthesis of orthogonally protected bacterial, rare-sugar and D-glycosamine building blocks.Nature protocols · 2013Article
Corrections and comments
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Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
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.
Indexed as
Identifiers
22955694What OpenQuestion holds
Registered trials
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