Synthesis of Pseudomonas aeruginosa lipopolysaccharide core antigens containing 7-O-carbamoyl-L-glycero-alpha-D-manno-heptopyranosyl residues.

@article{Reiter1999SynthesisOP,
  title={Synthesis of Pseudomonas aeruginosa lipopolysaccharide core antigens containing 7-O-carbamoyl-L-glycero-alpha-D-manno-heptopyranosyl residues.},
  author={Andreas Reiter and Alla Zamyatina and H Schindl and Andreas Hofinger and Paul Kosma},
  journal={Carbohydrate research},
  year={1999},
  volume={317 1-4},
  pages={
          39-52
        }
}
The monosaccharide allyl 7-O-carbamoyl-L-glycero-alpha-D-manno- heptopyranoside, the reducing disaccharide 7-O-carbamoyl-L-glycero-alpha-D- manno-heptopyranosyl-(1-->3)-L-glycero-D-manno-heptopyranose and the disaccharides allyl 7-O-carbamoyl-L-glycero-alpha-D-manno-heptopyranosyl-(1-->3)-L-glycero- beta- and alpha-D-manno-heptopyranoside were prepared in good yields. The 7-O-carbamoyl substituent was regioselectively introduced via NH3-NH4HCO3 treatment of a 6,7-O-carbonate group… Expand
Synthesis and immunochemical characterization of neoglycoproteins containing epitopes of the inner core region of Pseudomonas aeruginosa RNA group I lipopolysaccharide
The disaccharide allyl 2-acetamido-2-deoxy-α-D-galactopyranosyl-(1→3)-7-O-carbamoyl-L- glyceroα-D-manno-heptopyranoside 5 (GalNAc-cmHep-allyl) was synthesized starting from 1 and 2. Compound 5,Expand
Chemical synthesis of the core oligosaccharide of bacterial lipopolysaccharide
Publisher Summary Several in-depth reviews on the synthesis of higher-carbon bacterial sugars and of oligosaccharide structures of the core region of bacterial lipopolysaccharides (LPSs) have beenExpand
Burkholderia cenocepacia BC2L-C Is a Super Lectin with Dual Specificity and Proinflammatory Activity
TLDR
The TNF-α-like domain triggers IL-8 production in cultured airway epithelial cells in a carbohydrate-independent manner, and is therefore proposed to play a role in the dysregulated proinflammatory response observed in B. cenocepacia lung infections. Expand
Burkholderia cenocepacia lectin A binding to heptoses from the bacterial lipopolysaccharide.
TLDR
The crystal structure of BC2L-A complexed with the methyl-heptoside confirmed the location of the carbohydrate ring in the binding site and elucidated the orientation of the glycol tail, in agreement with NMR data. Expand
Synthesis of tools for raising antibodies against moenomycin epitopes and initial immunological studies
Abstract The moenomycins A and C 1 as well as penta-, di- and monosaccharide analogues have been conjugated to BSA and biotin, respectively. The moenomycin A–BSA conjugates have been used to raiseExpand

References

SHOWING 1-10 OF 18 REFERENCES
Stereoselective ring-opening of β-D-mannopyranose 1,2-(alkyl orthoacetates)☆
Abstract The stability towards alkali of the 3,4,6-tri-O-acetyl-β- D -mannose 1,2-(alkyl orthoacetates) provides a route to the corresponding 3,4,6-tri-O-benzyl-β- D -mannose 1,2-(alkylExpand
General strategy for structural analysis of the oligosaccharide region of lipooligosaccharides. Structure of the oligosaccharide component of Pseudomonas aeruginosa IATS serotype 06 mutant R5 rough-type lipopolysaccharide.
TLDR
The glycan structure of the LOS was elucidated by employing a novel strategy that involved the use of one- and two-dimensional nuclear magnetic resonance techniques and mass spectrometric based methods on the backbone oligosaccharide obtained from the Los by deacylation, dephosphorylation, and reduction of the terminal glucosamine. Expand
Structural elucidation of the lipopolysaccharide core region of the O-chain-deficient mutant strain A28 from Pseudomonas aeruginosa serotype 06 (International Antigenic Typing Scheme)
TLDR
The lipopolysaccharide of the Pseudomonas aeruginosa serotype 06 rough-type mutant A28 was isolated by a modified phenol-chloroform-petroleum ether extraction method and a structural model for the complete core oligosaccharide is proposed. Expand
Synthesis of linear oligosaccharides: l-glycero-α-d-manno-heptopyranosyl derivatives of allyl α-glycosides of d-glucose, kojibiose, and 3-O-α-kojibiosyl-d-glucose, substrates for synthetic antigens
Abstract Synthesis of the title oligosaccharides was performed with the use of peracetylated l - glycero -β- d - manno -heptosyl trichloroacetimidate as the heptosyl donor and (oligo)glucosylExpand
Structural elucidation of the lipopolysaccharide core regions of the wild-type strain PAO1 and O-chain-deficient mutant strains AK1401 and AK1012 from Pseudomonas aeruginosa serotype O5.
TLDR
Deoxycholate/PAGE of the LPS from the rough mutant AK1401 indicated two bands near the dye front with mobilities similar to those of the parent strain, indicating that both LPS contain a complete core and a species comprising a core and one repeating unit. Expand
Bausteine von Oligosacchariden, IC. Darstellung von synthetischen Antigenen der inneren Core‐Region von Lipopolysacchariden durch Copolymerisation mit Acrylamid
Building Units of Oligosaccharides, IC. – Preparation of Synthetic Antigens of the Inner Core Region of Lipopolysaccharides by Copolymerisation with Acrylamide Besides L-α-D-Hepp-OAll (5), theExpand
Synthesis of 3-(2-aminoethylthio)propyl glycosides.
TLDR
Anomeric pairs of 3-(2-aminoethylthio)propyl d -galactopyranoside, and 2-acetamido-2-deoxy- d -glucopyrside were prepared by addition of 2- aminoethanethiol to the corresponding, anomeric, allyl glycosides. Expand
Bausteine von Oligosacchariden, CV. Synthese des Pentasaccharids L‐α‐D‐Hep‐(1→3)‐L‐α‐D‐Hep‐(1→5)‐α‐Kdo‐(2→6)‐β‐D‐GlcNhm‐(1→6)‐D‐GlcNhm der linearen Core‐ und Lipoid‐A‐Struktur von Lipopolysacchariden
Building Units of Oligosaccharides, CV. – Synthesis of the Pentasaccharide L-α-D-Hep-(13)-L-α-D-Hep-(15)-α-Kdo-(26)-β-D-GlcNhm-(16)-D-GlcNhm of the Linear Core and Lipoid A Structure ofExpand
Monoclonal antibodies that distinguish inner core, outer core, and lipid A regions of Pseudomonas aeruginosa lipopolysaccharide
TLDR
In order to examine the immunochemistry of the core-lipid A region of Pseudomonas aeruginosa lipopolysaccharide (LPS), monoclonal antibodies specific for this region were produced in mice to precisely define immunodominant epitopes within the LPS core region. Expand
Michael addition as the key step in the syntheses of sialyloligosaccharide–protein conjugates from N-acryloylated glycopyranosylamines
Sialic acid and sialyloligosaccharides having terminal N-acryloyl functionality in their aglycone portions were efficiently conjugated to the lysine groups of proteins through Michael additions underExpand
...
1
2
...