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A versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid starting from d-serine. 2019

Manuel Gintner, and Yuko Yoneda, and Christoph Schmölzer, and Christian Denner, and Hanspeter Kählig, and Walther Schmid
AG Schmid, Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria. Electronic address: manuel.gintner@univie.ac.at.

Legionaminic acid and 4-epi-legionaminic acid are 5,7-diacetamido nonulosonic acids and are assumed to play a crucial role in the virulence of Legionella pneumophila, the causative agent of Legionnaires' disease. Moreover, they are ideal target motifs for the development of vaccines and pathogen detection. Herein, we present a versatile de novo synthesis of legionaminic acid and 4-epi-legionaminic acid. Starting from simple d-serine, the C9-backbone is built up by two CC-bond formation reactions. First, the protected d-serine motif is elongated utilizing a highly stereoselective nitroaldol reaction to give a C6-precursor of desired d-rhamno configuration. Second, an indium-mediated allylation is employed to further elongate the carbon backbone and introduce a masked α-keto acid function.

UI MeSH Term Description Entries
D007204 Indium A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.
D007700 Kinetics The rate dynamics in chemical or physical systems.
D009574 Nitro Compounds Compounds having the nitro group, -NO2, attached to carbon. When attached to nitrogen they are nitramines and attached to oxygen they are NITRATES. Nitrated Compounds
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D006575 Heterocyclic Compounds, 3-Ring A class of heterocyclic compounds that include a three-ring fused structure. Both aromatic or non-aromatic ring structures are included in this category. Fused Heterocyclic Compounds, Three-Ring,Heterocyclic Cpds, 3 Ring,Three Ring Heterocyclic Compounds,3-Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Three Ring,Heterocyclic Compounds, 3 Ring
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D012694 Serine A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids. L-Serine,L Serine
D012794 Sialic Acids A group of naturally occurring N-and O-acyl derivatives of the deoxyamino sugar neuraminic acid. They are ubiquitously distributed in many tissues. N-Acetylneuraminic Acids,Acids, N-Acetylneuraminic,Acids, Sialic,N Acetylneuraminic Acids
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013400 Sugar Acids MONOSACCHARIDES and other sugars that contain one or more carboxylic acid moieties. Acids, Sugar

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