Total Synthesis of Zwitterionic Tetrasaccharide Repeating Unit from Bacteroides fragilis ATCC 25285/NCTC 9343 Capsular Polysaccharide PS A1 with Alternating Charges on Adjacent Monosaccharides

2018 ◽  
Vol 20 (15) ◽  
pp. 4526-4530 ◽  
Author(s):  
Pradheep Eradi ◽  
Samir Ghosh ◽  
Peter R. Andreana
Keyword(s):  
Total Synthesis ◽  
Capsular Polysaccharide ◽  
Bacteroides Fragilis

scholarly journals The capsular polysaccharide of Bacteroides fragilis comprises two ionically linked polysaccharides.

1992 ◽  
Vol 267 (25) ◽  
pp. 18230-18235
Author(s):  
A.O. Tzianabos ◽  
A Pantosti ◽  
H Baumann ◽  
J.R. Brisson ◽  
H.J. Jennings ◽  
...  
Keyword(s):  
Capsular Polysaccharide ◽  
Bacteroides Fragilis

scholarly journals Mutational analysis of genes implicated in LPS and capsular polysaccharide biosynthesis in the opportunistic pathogen Bacteroides fragilis

Microbiology ◽  
2009 ◽  
Vol 155 (4) ◽  
pp. 1039-1049 ◽  
Author(s):  
Sheila Patrick ◽  
Simon Houston ◽  
Zubin Thacker ◽  
Garry W. Blakely
Keyword(s):  
Capsular Polysaccharide ◽  
Mutational Analysis ◽  
Bacteroides Fragilis ◽  
Gene Clusters ◽  
Opportunistic Pathogen ◽  
Extracellular Polysaccharides ◽  
Phase Variable ◽  
Multiple Gene ◽  
Polysaccharide Biosynthesis ◽  
Group 1

The obligate anaerobe Bacteroides fragilis is a normal resident of the human gastrointestinal tract. The clinically derived B. fragilis strain NCTC 9343 produces an extensive array of extracellular polysaccharides (EPS), including antigenically distinct large, small and micro- capsules. The genome of NCTC 9343 encodes multiple gene clusters potentially involved in the biosynthesis of EPS, eight of which are implicated in production of the antigenically variable micro-capsule. We have developed a rapid and robust method for generating marked and markerless deletions, together with efficient electroporation using unmodified plasmid DNA to enable complementation of mutations. We show that deletion of a putative wzz homologue prevents production of high-molecular-mass polysaccharides (HMMPS), which form the micro-capsule. This observation suggests that micro-capsule HMMPS constitute the distal component of LPS in B. fragilis. The long chain length of this polysaccharide is strikingly different from classical enteric O-antigen, which consists of short-chain polysaccharides. We also demonstrate that deletion of a putative wbaP homologue prevents expression of the phase-variable large capsule and that expression can be restored by complementation. This suggests that synthesis of the large capsule is mechanistically equivalent to production of Escherichia coli group 1 and 4 capsules.

Structural elucidation of the capsular polysaccharide of Bacteroides fragilis strain 23745M1

1995 ◽  
Vol 275 (2) ◽  
pp. 333-341 ◽  
Author(s):  
Viliam Pavliak ◽  
Dušan Uhrín ◽  
Jean-Robert Brisson ◽  
Arthur O. Tzianabos ◽  
Dennis L. Kasper ◽  
...  
Keyword(s):  
Capsular Polysaccharide ◽  
Bacteroides Fragilis ◽  
Structural Elucidation

scholarly journals Total synthesis of aStreptococcus pneumoniaeserotype 12F CPS repeating unit hexasaccharide

2017 ◽  
Vol 13 ◽  
pp. 164-173 ◽  
Author(s):  
Peter H Seeberger ◽  
Claney L Pereira ◽  
Subramanian Govindan
Keyword(s):  
Total Synthesis ◽  
Capsular Polysaccharide ◽  
Severe Disease ◽  
Building Blocks ◽  
Positive Bacterium ◽  
Linear Approach ◽  
Starting Point ◽  
Branching Points ◽  
Glycoconjugate Vaccines ◽  
Sequential Assembly

The Gram-positive bacteriumStreptococcus pneumoniaecauses severe disease globally. Vaccines that preventS. pneumoniaeinfections induce antibodies against epitopes within the bacterial capsular polysaccharide (CPS). A better immunological understanding of the epitopes that protect from bacterial infection requires defined oligosaccharides obtained by total synthesis. The key to the synthesis of theS. pneumoniaeserotype 12F CPS hexasaccharide repeating unit that is not contained in currently used glycoconjugate vaccines is the assembly of the trisaccharide β-D-GalpNAc-(1→4)-[α-D-Glcp-(1→3)]-β-D-ManpNAcA, in which the branching points are equipped with orthogonal protecting groups. A linear approach relying on the sequential assembly of monosaccharide building blocks proved superior to a convergent [3 + 3] strategy that was not successful due to steric constraints. The synthetic hexasaccharide is the starting point for further immunological investigations.

scholarly journals Orientations of the Bacteroides fragilis Capsular Polysaccharide Biosynthesis Locus Promoters during Symbiosis and Infection

2010 ◽  
Vol 192 (21) ◽  
pp. 5832-5836 ◽  
Author(s):  
Erin B. Troy ◽  
Vincent J. Carey ◽  
Dennis L. Kasper ◽  
Laurie E. Comstock
Keyword(s):  
Capsular Polysaccharide ◽  
Bacteroides Fragilis ◽  
Polysaccharide Biosynthesis

ABSTRACT Orientations of the seven invertible polysaccharide biosynthesis locus promoters of B acteroides fragilis were determined from bacteria grown in vitro, from feces of monoassociated and complex colonized mice, and from B. fragilis-induced murine abscesses. Bacteria grown in vivo have greater variability in orientation of polysaccharide locus promoters than culture-grown organisms.

scholarly journals Bacteroides fragilis NCTC9343 Produces at Least Three Distinct Capsular Polysaccharides: Cloning, Characterization, and Reassignment of Polysaccharide B and C Biosynthesis Loci

2000 ◽  
Vol 68 (11) ◽  
pp. 6176-6181 ◽  
Author(s):  
Michael J. Coyne ◽  
Wiltrud Kalka-Moll ◽  
Arthur O. Tzianabos ◽  
Dennis L. Kasper ◽  
Laurie E. Comstock
Keyword(s):  
Animal Models ◽  
Capsular Polysaccharide ◽  
Bacteroides Fragilis ◽  
Prototype Strain ◽  
Rodent Model ◽  
Type Structure ◽  
Capsular Polysaccharides ◽  
Chromosomal Deletion ◽  
Polysaccharide Complex

ABSTRACT Bacteroides fragilis produces a capsular polysaccharide complex (CPC) that is directly involved in its ability to induce abscesses. Two distinct capsular polysaccharides, polysaccharide A (PS A) and PS B, have been shown to be synthesized by the prototype strain for the study of abscesses, NCTC9343. Both of these polysaccharides in purified form induce abscesses in animal models. In this study, we demonstrate that the CPC of NCTC9343 is composed of at least three distinct capsular polysaccharides: PS A, PS B, and PS C. A previously described locus contains genes whose products are involved in the biosynthesis of PS C rather than PS B as was originally suggested. The actual PS B biosynthesis locus was cloned, sequenced, and found to contain 22 genes in an operon-type structure. A mutant with a large chromosomal deletion of the PS B biosynthesis locus was created so that the contribution of PS B to the formation of abscesses could be assessed in a rodent model. Although purified PS B can induce abscesses, removal of this polysaccharide does not attenuate the organism's ability to induce abscesses.

ChemInform Abstract: Structural Elucidation of the Capsular Polysaccharide of Bacteroides fragilis Strain 23745M1.

ChemInform ◽  
2010 ◽  
Vol 27 (5) ◽  
pp. no-no
Author(s):  
V. PAVLIAK ◽  
D. UHRIN ◽  
J.-R. BRISSON ◽  
A. O. TZIANABOS ◽  
D. L. KASPER ◽  
...  
Keyword(s):  
Capsular Polysaccharide ◽  
Bacteroides Fragilis ◽  
Structural Elucidation
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