ArticleNature protocols2013
Synthesis of orthogonally protected bacterial, rare-sugar and D-glycosamine building blocks.
Article in Nature protocols, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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24 citing papers in PubMed, 95 citations in OpenAlex.
- Development of Fluorogenic Probes to Detect Glycan-Degrading Enzymes in Bacteria.ACS infectious diseases · 2026Article
- Selective epimerization of GlcNAc to GalNAc through steady-state tuning under kinetic network control.Nature chemistry · 2026Article
- AssessingACS infectious diseases · 2026Article
- Total Synthesis and Anomeric Configuration Revision of Zwitterionic Polysaccharide A2's Pentasaccharide Repeating Unit fromJACS Au · 2025Article
- Biocatalytic cascade combining an engineered pyranose 2-oxidase and transaminases for the synthesis of amino sugars.RSC advances · 2025Article
- Synthesis of 2-Deoxyglycosides with Exclusive β-Configuration Using 2-SAc Glycosyl Bromide Donors.Molecules (Basel, Switzerland) · 2025Article
- Article
- Thioglycosides Act as Metabolic Inhibitors of Bacterial Glycan Biosynthesis.ACS infectious diseases · 2023Article
- Total Synthesis and Structural Studies of ZwitterionicJournal of the American Chemical Society · 2023Article
- Scalable Synthesis of Versatile Rare Deoxyamino Sugar Building Blocks from d-Glucosamine.The Journal of organic chemistry · 2023Article
- Sulfamate-TetheredThe Journal of organic chemistry · 2023Article
- Chemical tools to study bacterial glycans: a tale from discovery of glycoproteins to disruption of their function.Israel journal of chemistry · 2023Article
- Synthetic Zwitterionic Streptococcus pneumoniae Type 1 Oligosaccharides Carrying Labile O-Acetyl Esters.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis of Oligosaccharides Resembling theOrganic letters · 2022Article
- Facile and Scalable Route to Access Rare Deoxy Amino Sugars for Nonulosonic Acid Aldolase Biosynthesis.Frontiers in chemistry · 2022Article
- Exploratory N-Protecting Group Manipulation for the Total Synthesis of Zwitterionic Shigella sonnei Oligosaccharides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Chemical Synthesis and Immunological Evaluation of a Pentasaccharide Bearing Multiple Rare Sugars as a Potential Anti-pertussis Vaccine.Angewandte Chemie (International ed. in English) · 2020Article
- Synthesis of the pentasaccharide repeating unit of the O-antigen fromRSC advances · 2020Article
- Metabolic inhibitors of bacterial glycan biosynthesis.Chemical science · 2020Article
- Synthetic, Zwitterionic Sp1 Oligosaccharides Adopt a Helical Structure Crucial for Antibody Interaction.ACS central science · 2019Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Bacterial glycoconjugates comprise atypical deoxy amino sugars that are not present on the human cell surface, making them good targets for drug discovery and carbohydrate-based vaccine development. Unfortunately, they cannot be isolated with sufficient purity in acceptable amounts, and therefore chemical synthesis is a crucial step toward the development of these products. Here we describe a detailed protocol for the synthesis of orthogonally protected bacterial deoxy amino hexopyranoside (2,4-diacetamido-2,4,6-trideoxyhexose (DATDH), D-bacillosamine, D-fucosamine, and 2-acetamido-4-amino-2,4,6-trideoxy-D-galactose (AAT)), D-glucosamine and D-galactosamine building blocks starting from β-D-thiophenylmannoside. Readily available β-D-thiophenylmannoside was first converted into the corresponding 2,4-diols via deoxygenation or silylation at C6, followed by O3 acylation. The 2,4-diols were converted into 2,4-bis-trifluoromethanesulfonates, which underwent highly regioselective, one-pot, double-serial and double-parallel displacements by azide, phthalimide, acetate and nitrite ions as nucleophiles. Thus, D-rhamnosyl- and D-mannosyl 2,4-diols can be efficiently transformed into various rare sugars and D-galactosamine, respectively, as orthogonally protected thioglycoside building blocks on a gram scale in 1-2 d, in 54-85% overall yields, after a single chromatographic purification. This would otherwise take 1-2 weeks. D-Glucosamine building blocks can be prepared from β-D-thiophenylmannoside in four steps via C2 displacement of triflates by azide in 2 d and in 66-70% overall yields. These procedures have been applied to the synthesis of L-serine-linked trisaccharide of Neisseria meningitidis and a rare disaccharide fragment of the zwitterionic polysaccharide (ZPS) A1 (ZPS A1) of Bacteroides fragilis.
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