title: Structure elucidation and gene cluster annotation of the O-antigen of Escherichia coli O39; application of anhydrous trifluoroacetic acid for selective cleavage of glycosidic linkages.
abstract: O-Polysaccharide (O-antigen) accompanied by a minor mannan was isolated from the lipopolysaccharide of Escherichia coli O39 and studied by component analyses, methylation, Smith degradation, mass spectrometry, and 1D and 2D NMR spectroscopy. In addition, a new approach, solvolysis with anhydrous trifluoroacetic acid, was applied to cleave selectively the rhamnosidic linkage. The following structure of the O-polysaccharide was established: α--D-Galpl-->3-->3)-β-D-Quip4N(R3Hb)-(1-->2)-α-D-Manp-(l-->4)-α-L-Rhap-(1-->3)-α-D-GlcpNAc-(1--> where D-Qui4N(R3Hb) indicates 4,6-dideoxy-4-[(R)-3-hydroxybutanoylamino]-d-glucose. The O-antigen gene cluster of E. coli O39 has been sequenced. The gene functions were tentatively assigned by a comparison with sequences in the available databases and found to be in agreement with the O-polysaccharide structure.
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia. Electronic address: perepel@ioc.ac.ru.
authors.forename: Andrei V
authors.initials: AV
authors.lastname: Perepelov
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
authors.forename: Andrei V
authors.initials: AV
authors.lastname: Filatov
authors.affiliation: TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.
authors.forename: Quan
authors.initials: Q
authors.lastname: Wang
authors.affiliation: Institute of Immunology, Federal Medical-Biological Agency, Moscow, Russia.
authors.forename: Vyacheslav L
authors.initials: VL
authors.lastname: L'vov
authors.affiliation: TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.
authors.forename: Ye
authors.initials: Y
authors.lastname: Qian
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Shashkov
authors.affiliation: TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.affiliation: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
authors.forename: Yuriy A
authors.initials: YA
authors.lastname: Knirel
mesh_terms: D002240:Carbohydrate Sequence; D004926:Escherichia coli / Q000737:chemistry* / Q000235:genetics; D029968:Escherichia coli Proteins / Q000737:chemistry* / Q000235:genetics; D006031:Glycosylation; D006868:Hydrolysis; D058977:Molecular Sequence Annotation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D005810:Multigene Family; D019081:O Antigens / Q000737:chemistry* / Q000302:isolation & purification; D012210:Rhamnose / Q000737:chemistry; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D029968:Escherichia coli Proteins; D019081:O Antigens; D014269:Trifluoroacetic Acid; D012210:Rhamnose
keywords: Bacterial polysaccharide structure; Escherichia coli; Lipopolysaccharide; O-Antigen; O-Antigen gene cluster