Synthesis of an O-sulfo Lewis(X) analog as glycolipid antigen. 2011

Shuhei Ueno, and Shigeomi Horito
Department of Biological Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.

The title compound containing dihydroceramide as a ligand for CD1d was accomplished using the mannosyl, glucosaminyl, and fucosyl donors, and a sphinganine analogue, as suitable building blocks. The 2-O-unprotected mannosyl donor was coupled effectively with the sphinganine analog to afford the mannnosyl sphinganine derivative. The coupling of the glucosaminyl donor with the mannnosyl sphinganine acceptor required triflic acid as a promoter and the promoter change to silver triflate led to the undesired glycal production. The reduction of azide group using Zn powder was the key process, in which the amount of acetic acid was restricted to avoid the benzoyl migration and N-trichloroacetyl deprotection. The trisaccharide glycolipid was sulfonated at the 3-position of fucose moiety.

UI MeSH Term Description Entries
D007114 Immunization Deliberate stimulation of the host's immune response. ACTIVE IMMUNIZATION involves administration of ANTIGENS or IMMUNOLOGIC ADJUVANTS. PASSIVE IMMUNIZATION involves administration of IMMUNE SERA or LYMPHOCYTES or their extracts (e.g., transfer factor, immune RNA) or transplantation of immunocompetent cell producing tissue (thymus or bone marrow). Immunologic Stimulation,Immunostimulation,Sensitization, Immunologic,Variolation,Immunologic Sensitization,Immunological Stimulation,Sensitization, Immunological,Stimulation, Immunologic,Immunizations,Immunological Sensitization,Immunological Sensitizations,Immunological Stimulations,Sensitizations, Immunological,Stimulation, Immunological,Stimulations, Immunological,Variolations
D006017 Glycolipids Any compound containing one or more monosaccharide residues bound by a glycosidic linkage to a hydrophobic moiety such as an acylglycerol (see GLYCERIDES), a sphingoid, a ceramide (CERAMIDES) (N-acylsphingoid) or a prenyl phosphate. (From IUPAC's webpage) Glycolipid
D016256 Lewis X Antigen A trisaccharide antigen expressed on glycolipids and many cell-surface glycoproteins. In the blood the antigen is found on the surface of NEUTROPHILS; EOSINOPHILS; and MONOCYTES. In addition, Lewis X antigen is a stage-specific embryonic antigen. Antigens, CD15,CD15 Antigens,Le(X) Antigen,Leu-M1 Antigens,Lewis X Related Antigens,SSEA-1,SSEA-1 Determinant,Stage-Specific Embryonic Antigen-1,3 alpha-Fucosyl-N-Acetyl Lactosamine,CD15 Antigen,Galbeta(1-4)Fucalpha(1-3)GlcNAc,Hapten X,Lewis X Hapten,SSEA 1,3 alpha Fucosyl N Acetyl Lactosamine,Antigen, Lewis X,Embryonic Antigen-1, Stage-Specific,Leu M1 Antigens,SSEA 1 Determinant,Stage Specific Embryonic Antigen 1,X Antigen, Lewis,X Hapten, Lewis

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