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
Diversity-Oriented Synthesis of Glycosylphosphatidylinositol Probes Based on an Orthogonally Protected Pentasaccharide.
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DOI: 10.1021/acs.orglett.3c00448
Abstract: Two glycosylphosphatidylinositol (GPI) derivatives having an alkynyl group at different positions were derived from the same orthogonally protected pentasaccharide that in turn was assembled by a convergent [3+2] glycosylation strategy. The resultant alkynylated GPIs are… read more here.
Keywords: synthesis glycosylphosphatidylinositol; orthogonally protected; oriented synthesis; diversity oriented ... See more keywords
Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01513
Abstract: Natural products containing aminocyclopentanes are common secondary metabolites, often biologically active. This work aims at the preparation of a useful synthon for total synthesis containing orthogonally protected amines. To this end, furfural and two amines… read more here.
Keywords: protected diaminocyclopentenones; orthogonally protected; synthesis; diaminocyclopentenones synthons ... See more keywords
Chemical Synthesis of an Orthogonally Protected 5,7-Diamino-3,5,7,9-tetradeoxy-d-glycero-l-gluco-2-nonulosonic Acid from N-Acetylneuraminic Acid.
Sign Up to like & getrecommendations! Published in 2024 at "Organic letters"
DOI: 10.1021/acs.orglett.4c01861
Abstract: Bacterial nonulosonic acids (NulOs), which feature a nine-carbon backbone, are associated with the biological functions of bacterial glycans. Here, an orthogonally protected 5-amino-7-azido-3,5,7,9-tetradeoxy-d-glycero-l-gluco-2-nonulosonic acid related to Fusobacterium nucleatum ATCC 23726 NulO was synthesized from N-acetylneuraminic… read more here.
Keywords: tetradeoxy glycero; glycero gluco; gluco nonulosonic; nonulosonic acid ... See more keywords
Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.
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DOI: 10.1021/acs.orglett.9b00125
Abstract: Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the… read more here.
Keywords: ring opening; synthesis orthogonally; orthogonally protected; scalable synthesis ... See more keywords
Synthesis of Four Orthogonally Protected Rare l-Hexose Thioglycosides from d-Mannose by C-5 and C-4 Epimerization
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DOI: 10.3390/molecules27113422
Abstract: l-Hexoses are important components of biologically relevant compounds and precursors of some therapeuticals. However, they typically cannot be obtained from natural sources and due to the complexity of their synthesis, their commercially available derivatives are… read more here.
Keywords: rare hexose; orthogonally protected; hexose thioglycosides; protected rare ... See more keywords