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Synthesis of alpha-lactosyl-(1-->3)-L-glycero-alpha-D-manno-heptopyranoside, a partial oligosaccharide structure expressed within the lipooligosaccharide produced by Neisseria gonorrhoeae strain 15253.
Carbohydr Res
January 2002
Department of Biochemistry and Biotechnology, Tottori University, Koyama-Minami 4-101, Tottori 680-8553, Japan.
The glycosyl donor, hepta-O-benzyl-beta-lactosyl trichloroacetimidate (4) was prepared by treating hepta-O-benzyl-lactose with trichloroacetonitrile in the presence of potassium carbonate. The acceptor, methyl 2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (8) was synthesized by hydrolysis of a 3,4-butane diacetal of methyl L-glycero-alpha-D-manno-oct-enopyranoside and subsequent benzylidenation. Glycosidation of the donor 4 with the acceptor 8 in 1,4-dioxane using Me(3)SiOTf as a promoter for 1 h at room temperature gave methyl (2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->3)-2-O-benzyl-4,6-O-benzylidene-7,8-dideoxy-alpha-D-manno-oct-7-enopyranoside (9) as a major product (59%).
View Article and Find Full Text PDFMonoclonal antibodies against Haemophilus influenzae lipopolysaccharides: clone MAHI 4 binding to a pentasaccharide containing terminal beta-Gal residues and clone MAHI 10 recognizing terminal phosphorylated saccharide residues.
Microb Pathog
November 1996
Clinical Research Centre, NOVUM, Karolinska Institute, Huddinge Hospital, Sweden.
Mouse monoclonal antibodies MAHI 4 and MAHI 10 reactive with Haemophilus influenzae lipopolysaccharide (LPS), were generated by fusing mouse myeloma cells with spleen cells of mice immunized with H. influenzae strain RM.7004-XP-1.
View Article and Find Full Text PDFCharacterization of two transposon mutants from Haemophilus influenzae type b with altered lipooligosaccharide biosynthesis.
Biochemistry
May 1996
Department of Pharmaceutical Chemistry, University of California, San Francisco 94143-0446, USA.
Two isogenic mutants of Haemophilus influenzae type b (Hib) strain A2 were prepared by random m-Tn3(Cm) insertions into the 7.4-kb lsg (lipooligosaccharide synthesis genes) region of Hib DNA, which consists of seven complete and one partial open reading frame (orfs). Compared to the parent A2 strain which produces a complex mixture of lipooligosaccharides (LOS), the mutant strains 281.
View Article and Find Full Text PDFInhibition of human immunodeficiency virus infection by heparin derivatives.
AIDS Res Hum Retroviruses
January 1996
Commissariat à l'Energie Atomique, Centre de Recherches du Service de Santé des Armées, Fontenay-aux-Roses, France.
Heparin (Hep) and sulfated polysaccharides (SPs) have been reported to inhibit HIV infection in vitro. In vivo, anticoagulant activity and reduced bioavailability were found to limit the antiviral effects of Hep. In this investigation, three nonanticoagulant N-acylated Hep conjugates [OI1:3Hep, Pal1:5Hep, and Pal1:5Hep(SO4)] were compared to Hep for their ability to interact with HIV replication in CD4-positive cell lines and PBMCs.
View Article and Find Full Text PDFThe tetrasaccharide L-alpha-D-heptose1-->2-L-alpha-D-heptose1--> 3-L-alpha-D-heptose1-->(3-deoxy-D-manno-octulosonic acid) and phosphate in lipid A define the conserved epitope in Haemophilus lipopolysaccharides recognized by a monoclonal antibody.
Infect Immun
September 1995
Department of Immunology, Microbiology, Pathology and Infectious Diseases, Karolinska Institute, Huddinge, Sweden.
A murine monoclonal antibody, MAHI 3 (immunoglobulin G2b), that is broadly reactive with Haemophilus influenzae lipopolysaccharides (LPSs) but nonreactive with all enterobacterial LPSs tested was generated by fusing mouse myeloma cells with spleen cells of BALB/c mice immunized with azide-killed H. influenzae RM.7004.
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