Definitive Structural Assessment of Enterococcal Diheteroglycan

Krylov, Vadim B.; Gerbst, Alexey G.; Argunov, Dmitry A.; Dmitrenok, Andrey S.; Shashkov, Alexander S.; Kaczyński, Zbigniew; Hüebner, Johannes; Holst, Otto; Nifantiev, Nikolay E.

doi:10.1002/chem.201405857

Cited by 30 publications

(35 citation statements)

References 17 publications

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“…Previously, a preparative protocol for the PIF rearrangement of different glycosides bearing an allyl group as a temporary protecting group at anomeric position was developed . In this communication, we expand the scope of this process by using an aglycon that can act as a leaving group during glycosylation.…”

Section: Resultsmentioning

confidence: 99%

“…This was then subjected to the PIF rearrangement (Scheme ). The standard protocol for this rearrangement, which was successfully applied in the synthesis of oligosaccharides related to polysaccharides from Aspergillus fumigatus ,, Enterococcus feacalis , Chordaria flagelliformis , involves treatment with a Py · SO 3 /HSO 3 Cl mixture, followed by neutralization with NaHCO 3 , and solvolytic desulfation in the presence of acidic resin IR‐120 (H + ). Unfortunately, under these conditions substrate 9 gave only 27 % of target disaccharide 16 (Scheme , Table , entry 1).…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we reported a pyranoside‐into‐furanoside (PIF) rearrangement as an original and useful tool for the preparation of a variety of protected furanosides from the corresponding pyranosides . In this paper, we describe the use of the PIF rearrangement for the efficient synthesis of a tetrasaccharide related to a galactan I motif.…”

Section: Introductionmentioning

confidence: 99%

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Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae

2017

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An efficient strategy for synthesis of a spacer‐armed tetrasaccharide related to galactan I of Klebsiella pneumoniae is described, which uses newly developed acid‐free conditions for the pyranoside‐into‐furanoside (PIF) rearrangement of a digalactoside bearing a 4‐pentenyl group at the anomeric position. The 4‐pentenyl aglycon was successfully used both as a leaving group in the glycosylation of 3‐(trifluoroacetamido)propanol, and as a temporary anomeric protecting group, allowing conversion into an imidate donor. Regioselective coupling of the disaccharide blocks gave the desired tetrasaccharide sequence required for investigation of the interaction of galactan I with immune‐system proteins.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae

2017

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“…8,9 The herein reported first syntheses of heterosaccharides related to the galactomannan from A. fumigatus were performed with the use of PIF-rearrangement as a key step.…”

Section: Resultsmentioning

confidence: 99%

Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus

2015

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Aspergillus fumigatus is a very common fungus with high pathogenic potential for immunosuppressed hospital patients. A. fumigatus galactomannan, being the part of its cell wall, is considered as a promising candidate for vaccine and diagnostic test-systems. In this article we report the convergent synthesis of pentasaccharide fragments of the galactomannan containing the β-(1→5)-linked galactofuranoside chain attached to O-3 or O-6 of a spacer-armed mannopyranoside residue. The synthesis of selectively protected galactofuranoside precursors has been performed using recently developed pyranoside-into-furanoside (PIF) rearrangement. For assembling the target galactomannan structures the [1 + 2 + 2]-scheme was applied. This strategy was shown to be highly efficient and can easily be extended to the synthesis of longer fragments of thegalactomannan.

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“…Fragments of the capsule-like diheteroglycan (DHG) (Table 2 ) were recently synthesized and characterized as a promising vaccine candidate (Krylov et al. 2015 ).…”

Section: Approaches For Production Of Glycoconjugate Vaccinesmentioning

confidence: 99%

Potential targets for next generation antimicrobial glycoconjugate vaccines

Micoli¹,

Costantino

Adamo

2018

FEMS Microbiology Reviews

143

109

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Cell surface carbohydrates have been proven optimal targets for vaccine development. Conjugation of polysaccharides to a carrier protein triggers a T-cell-dependent immune response to the glycan moiety. Licensed glycoconjugate vaccines are produced by chemical conjugation of capsular polysaccharides to prevent meningitis caused by meningococcus, pneumococcus and Haemophilus influenzae type b. However, other classes of carbohydrates (O-antigens, exopolysaccharides, wall/teichoic acids) represent attractive targets for developing vaccines. Recent analysis from WHO/CHO underpins alarming concern toward antibiotic-resistant bacteria, such as the so called ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa and Enterobacter spp.) and additional pathogens such as Clostridium difficile and Group A Streptococcus. Fungal infections are also becoming increasingly invasive for immunocompromised patients or hospitalized individuals. Other emergencies could derive from bacteria which spread during environmental calamities (Vibrio cholerae) or with potential as bioterrorism weapons (Burkholderia pseudomallei and mallei, Francisella tularensis). Vaccination could aid reducing the use of broad-spectrum antibiotics and provide protection by herd immunity also to individuals who are not vaccinated.This review analyzes structural and functional differences of the polysaccharides exposed on the surface of emerging pathogenic bacteria, combined with medical need and technological feasibility of corresponding glycoconjugate vaccines.

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Definitive Structural Assessment of Enterococcal Diheteroglycan

Cited by 30 publications

References 17 publications

Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae

Pyranoside‐into‐Furanoside Rearrangement of 4‐Pentenyl Glycosides in the Synthesis of a Tetrasaccharide‐Related to Galactan I of Klebsiella pneumoniae

Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus

Potential targets for next generation antimicrobial glycoconjugate vaccines

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