title: Characterization of the physiological substrate for lipopolysaccharide heptosyltransferases I and II.
abstract: L-Glycero-D-manno-heptopyranose is a characteristic compound of many lipopolysaccharide (LPS) core structures of Gram-negative bacteria. In Escherichia coli two heptosyltransferases, namely WaaC and WaaF, are known to transfer L-glycero-D-manno-heptopyranose to Re-LPS and Rd(2)-LPS, respectively. It had been proposed that both reactions involve ADPL-glycero-D-manno-heptose as a sugar donor; however, the structure of this nucleotide sugar had never been completely elucidated. In the present study, ADPL-glycero-D-manno-heptose was isolated from a heptosyltransferase-deficient E. coli mutant, and its structure was determined by nuclear magnetic resonance spectroscopy and matrix-assisted laser-desorption/ionization time-of-flight mass spectrometry as ADPL-glycero-beta-D-manno-heptopyranose. This compound represented the sole constituent of the bacterial extract that was accepted as a sugar donor by heptosyltransferases I and II in vitro.
authors.affiliation: Medical and Biochemical Microbiology, Research Center Borstel, Germany.
authors.forename: S
authors.initials: S
authors.lastname: Gronow
authors.forename: C
authors.initials: C
authors.lastname: Oertelt
authors.forename: E
authors.initials: E
authors.lastname: Ervelä
authors.forename: A
authors.initials: A
authors.lastname: Zamyatina
authors.forename: P
authors.initials: P
authors.lastname: Kosma
authors.forename: M
authors.initials: M
authors.lastname: Skurnik
authors.forename: O
authors.initials: O
authors.lastname: Holst
mesh_terms: D000247:Adenosine Diphosphate Sugars / Q000378:metabolism; D004926:Escherichia coli / Q000201:enzymology; D016695:Glycosyltransferases / Q000378:metabolism*; D006539:Heptoses / Q000737:chemistry / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013379:Substrate Specificity / Q000502:physiology
chemical_list: D000247:Adenosine Diphosphate Sugars; D006539:Heptoses; C062615:glycero-alpha-manno-heptopyranose; C026312:glycero-manno-heptose; D016695:Glycosyltransferases; C086735:heptosyltransferase; C080934:lipooligosaccharide 1,5-heptosyltransferase