title: Structure of the O-polysaccharide of Providencia alcalifaciens O35 containing an N-[(S)-1-carboxyethyl]-L-alanine (alanopine) derivative of 4-amino-4,6-dideoxyglucose.
abstract: The O-polysaccharide of Providencia alcalifaciens O35 was studied by sugar and methylation analyses along with (1)H and (13)C NMR spectroscopy, including 2D (1)H,(13)C HMBC, and NOESY experiments in D2O and, to detect correlations for NH protons, in a 9:1 H2O/D2O mixture. A unique N-(1-carboxyethyl)alanine (alanopine, Alo) derivative of 4-amino-4,6-dideoxyglucose (Qui4N) was identified as the polysaccharide component. Alanopine was isolated by solvolysis of the polysaccharide with triflic acid followed by acid hydrolysis, and its (2S,4S)-configuration was determined by the specific optical rotation. The following structure of the O-polysaccharide was established (the d configuration of Qui4N was ascribed tentatively): [structure: see text].
authors.affiliation: ND Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation. olga.ovchinnikova@gmail.com
authors.forename: Olga G
authors.initials: OG
authors.lastname: Ovchinnikova
authors.forename: Olga A
authors.initials: OA
authors.lastname: Valueva
authors.forename: Nina A
authors.initials: NA
authors.lastname: Kocharova
authors.forename: Nikolay P
authors.initials: NP
authors.lastname: Arbatsky
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Maszewska
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Zablotni
authors.forename: Alexander S
authors.initials: AS
authors.lastname: Shashkov
authors.forename: Antoni
authors.initials: A
authors.lastname: Rozalski
authors.forename: Yuriy A
authors.initials: YA
authors.lastname: Knirel
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D002236:Carbohydrate Conformation; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D019081:O Antigens / Q000737:chemistry* / Q000302:isolation & purification; D011532:Providencia / Q000737:chemistry*
chemical_list: C492812:4-amino-4,6-dideoxyglucose; D019081:O Antigens; C026051:alanopine; D005944:Glucosamine; D000409:Alanine