A synthetic study towards the PSA1 tetrasaccharide repeating unit

Bos, Leendert J. van den; Boltje, Thomas J.; Provoost, Tom; Mazurek, Jarosław; Overkleeft, Herman S.; Marel, Gijsbert A. van der

doi:10.1016/j.tetlet.2007.02.067

Cited by 39 publications

(32 citation statements)

References 33 publications

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“…To improve the yield, we explored trichloroacetimidate as the protecting group [24] of 3-OH of b-rhamnoside 11 rather than Bz so that C4 inversion could be achieved in situ upon triflation (Scheme 4). Thet hioglycoside 11 was treated with trichloroacetonitrile and 1, 8-diazabicyclo [5.4.0]undec-7-ene (DBU) giving 15 in ay ield of 90 %.…”

Section: Resultsmentioning

confidence: 99%

Chemical Synthesis and Immunological Evaluation of a Pentasaccharide Bearing Multiple Rare Sugars as a Potential Anti‐pertussis Vaccine

et al. 2020

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With the infection rate of Bordetella pertussis at a 60‐year high, there is an urgent need for new anti‐pertussis vaccines. The lipopolysaccharide (LPS) of B. pertussis is an attractive antigen for vaccine development. With the presence of multiple rare sugars and unusual glycosyl linkages, the B. pertussis LPS is a highly challenging synthetic target. In this work, aided by molecular dynamics simulation and modeling, a pertussis‐LPS‐like pentasaccharide was chemically synthesized for the first time. The pentasaccharide was conjugated with a powerful carrier, bacteriophage Qβ, as a vaccine candidate. Immunization of mice with the conjugate induced robust anti‐glycan IgG responses with IgG titers reaching several million enzyme‐linked immunosorbent assay (ELISA) units. The antibodies generated were long lasting and boostable and could recognize multiple clinical strains of B. pertussis, highlighting the potential of Qβ‐glycan as a new anti‐pertussis vaccine.

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Section: Resultsmentioning

confidence: 99%

Chemical Synthesis and Immunological Evaluation of a Pentasaccharide Bearing Multiple Rare Sugars as a Potential Anti‐pertussis Vaccine

et al. 2020

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“…Chemical shifts (δ) are reported in ppm relative to remaining solvent peak CDCl 3 (δ = 7.26 ppm) for 1 H NMR spectra. 13 C NMR chemical shifts (δ) are reported in ppm relative to CDCl 3 (δ = 77.00 ppm).…”

Section: Scheme 3 Glycosylation and Anomerization Through Endocyclicmentioning

confidence: 99%

“…1.88 (s, 3H), 1.49 (s, 3H), 1.38 (s, 3H) 13. C NMR (100 MHz, CDCl 3 ) δ 170.3, 167.8, 167.3, 134.4, 134.2, 132.9, 131.7, 131.3, 131.2, 129.0, 128.2, 123.7, 99.8, 83.8, 71.8, 71.6, 71.0, 62.0, 54.3, 28.9, 20.6, 19.0.…”

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confidence: 99%

1,2-cis-Selective Formation of a Unique Amino-Containing Amino Glycoside by Endocyclic Cleavage Strategy

Manabe¹,

Ito²

2019

HETEROCYCLES

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“…There have been attempts to synthesize the PS-A of B. fragilis, however, the complete repeating unit was not reached nor was the oligosaccharide deprotected. [8] In other work a blocked but not deprotected trisaccharide repeating unit of Sp1 has been reported. [9] Here we report the first completed chemical synthesis and deprotection of a zwitterionic polysaccharide trisaccharide repeating unit 1 and the corresponding hexasaccharide 19 containing two repeating units.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Monomeric and Dimeric Repeating Units of the Zwitterionic Type 1 Capsular Polysaccharide from Streptococcus pneumoniae

Cui

Lipiński

et al. 2010

Chemistry A European J

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Zwitterionic polysaccharides (ZPSs) from Bacteroides fragilis and Streptococcus pneumoniae display unique T-cell activities. The first synthesis of a hexasaccharide representing two repeating units of the zwitterionic capsular polysaccharide from S. pneumoniae type 1 (Sp1) is reported. Key elements of the approach are stereoselective construction of 1,4-cis-alpha-galactose linkages based on a reactive trichloroacetimidate donor that incorporates a 6-O-acetyl group, which may contribute to the high alpha selectivity in glycosylation. After assembly of the fully protected hexasaccharide from five monosaccharide synthons 2-4, 24 and 25, selective deprotection of the primary hydroxyl groups of the four galactose residues followed by oxidation to the corresponding uronic acids provides hexasaccharide 19. The trisaccharide counterpart 1 was synthesized in similar fashion from three synthons, 2-4. This approach employed both conventional and dehydrative glycosylation methodologies and avoids the use of poorly reactive uronic acid derived glycosyl donors and acceptors.

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A synthetic study towards the PSA1 tetrasaccharide repeating unit

Cited by 39 publications

References 33 publications

Chemical Synthesis and Immunological Evaluation of a Pentasaccharide Bearing Multiple Rare Sugars as a Potential Anti‐pertussis Vaccine

Chemical Synthesis and Immunological Evaluation of a Pentasaccharide Bearing Multiple Rare Sugars as a Potential Anti‐pertussis Vaccine

1,2-cis-Selective Formation of a Unique Amino-Containing Amino Glycoside by Endocyclic Cleavage Strategy

Synthesis of Monomeric and Dimeric Repeating Units of the Zwitterionic Type 1 Capsular Polysaccharide from Streptococcus pneumoniae

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