Formation of a Covalent Adduct in Retaining β‐Kdo Glycosyl‐Transferase WbbB via Substrate‐Mediated Proton Relay
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DOI: 10.1002/cctc.202400769
Abstract: The GT99 domain of the membrane‐anchored WbbB glycosyltransferase (WbbBGT99) catalyzes the transfer of 3‐deoxy‐D‐manno‐oct‐2‐acid (β‐Kdo) to an O‐antigen saccharide acceptor with retention of stereochemistry. It has been proposed that the enzyme follows an unprecedented double‐displacement… read more here.
Keywords: covalent adduct; adduct; formation covalent; kdo ... See more keywords
Glycosylation of an N-Acetylated Glucosamine Disaccharide Using an Orthogonally Protected 3-Iodo-Kdo Fluoride Donor.
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DOI: 10.1002/open.202500141
Abstract: Kdo (3-Deoxy-d-manno-oct-2-ulosonic acid) is an essential sugar found in bacterial lipopolysaccharides with significant biomedical relevance. This study introduces an orthogonally protected 3-iodo-Kdo fluoride donor and demonstrates its coupling to a pre-synthesized β-(1→6)-linked N-acetylglucosamine disaccharide acceptor… read more here.
Keywords: iodo kdo; kdo; kdo fluoride; fluoride donor ... See more keywords
α-Stereoselective 3-Deoxy-d-manno-oct-2-ulosonoic Acid (Kdo) O-Glycosylation with a p-Toluenethioglycoside Donor by the (p-Tol)2SO/Tf2O Preactivation Strategy.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01430
Abstract: A convenient and efficient approach was developed to synthesize α-Kdo O-glycosides based on the Tf2O/(p-Tol)2SO preactivation strategy using peracetylated Kdo thioglycoside as a donor. Under the optimized reaction conditions, several O-glycoside products, including α-(2 →… read more here.
Keywords: preactivation strategy; tol 2so; kdo;
Stereodirecting Effect of C5-Carboxylate Substituents on the Glycosylation Stereochemistry of 3-Deoxy-d- manno-oct-2-ulosonic Acid (Kdo) Thioglycoside Donors: Stereoselective Synthesis of α- and β-Kdo Glycosides.
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DOI: 10.1021/jacs.7b09461
Abstract: The stereodirecting effect of C5-ester functions on the glycosylation stereoselectivity of 3-deoxy-d- manno-oct-2-ulosonic acid (Kdo) ethyl thioglycoside donors is presented. The coupling of 5- O-arylcarbonyl or acetyl protected Kdo thioglycosides with acceptors proceeds in an… read more here.
Keywords: deoxy manno; manno oct; thioglycoside donors; glycosylation ... See more keywords
TargeTron Inactivation of Chlamydia trachomatis gseA Results in a Lipopolysaccharide 3-Deoxy-d-Manno-Oct-2-Ulosonic Acid-Deficient Strain That Is Cytotoxic for Cells
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DOI: 10.1128/iai.00096-23
Abstract: All members of the family Chlamydiaceae have lipopolysaccharides (LPS) that possess a shared carbohydrate trisaccharide antigen, 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) that is functionally uncharacterized. A single gene, genus-specific epitope (gseA), is responsible for attaching the tri-Kdo… read more here.
Keywords: kdo; microscopy; gsea; acid ... See more keywords
Investigation of the Protection of the C4 Hydroxyl Group in Macrobicyclic Kdo Donors
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DOI: 10.3390/molecules28010102
Abstract: Chemical synthesis of 3-deoxy-d-manno-2-octulosonic acid (Kdo)-containing glycans, such as bacterial lipopolysaccharides (LPSs) and capsular polysaccharides (CPSs), is in high demand for the development of vaccines against pathogenic bacteria. We have recently achieved the complete α-stereoselective… read more here.
Keywords: kdo; protection hydroxyl; group; hydroxyl group ... See more keywords