ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Synthesis of chlamydia lipopolysaccharide haptens through the use of α-specific 3-iodo-Kdo fluoride glycosyl donors.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 36 citations in OpenAlex.
- Glycosylation of an N-Acetylated Glucosamine Disaccharide Using an Orthogonally Protected 3-Iodo-Kdo Fluoride Donor.ChemistryOpen · 2025Article
- Chemical Synthesis of Complex Carbohydrates.Handbook of experimental pharmacology · 2025Review
- Investigation of the Protection of the C4 Hydroxyl Group in Macrobicyclic Kdo Donors.Molecules (Basel, Switzerland) · 2022Article
- Chemoenzymatic Synthesis ofJournal of the American Chemical Society · 2020Article
- Stereocontrolled Synthesis of the Equatorial Glycosides of 3-Deoxy-d-manno-oct-2-ulosonic Acid: Role of Side Chain Conformation.Journal of the American Chemical Society · 2020Article
- Progress in Kdo-glycoside chemistry.Tetrahedron letters · 2016Article
- Synthesis of 5-O-oligoglucosyl extended α-(2→4)-Kdo disaccharides corresponding to inner core fragments of Moraxellaceae lipopolysaccharides.Carbohydrate research · 2016Article
- Scope and Limitations of 3-Iodo-Kdo Fluoride-Based Glycosylation Chemistry using N-Acetyl Glucosamine Acceptors.ChemistryOpen · 2015Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
A scalable approach towards high-yielding and (stereo)selective glycosyl donors of the 2-ulosonic acid Kdo (3-deoxy-D-manno-oct-2-ulosonic acid) is a fundamental requirement for the development of vaccines against Gram-negative bacteria. Herein, we disclose a short synthetic route to 3-iodo Kdo fluoride donors from Kdo glycal esters that enable efficient α-specific glycosylations and significantly suppress the elimination side reaction. The potency of these donors is demonstrated in a straightforward, six-step synthesis of a branched Chlamydia-related Kdo-trisaccharide ligand without the need for protecting groups at the Kdo glycosyl acceptor. The approach was further extended to include sequential iteration of the basic concept to produce the linear Chlamydia-specific α-Kdo-(2→8)-α-Kdo-(2→4)-α-Kdo trisaccharide in a good overall yield.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.