Linear synthesis of the hexasaccharide related to the repeating unit of the O-antigen from Shigella flexneri serotype 1d (I: 7,8)

Mitra, Ankita; Mukhopadhyay, Balaram

doi:10.1016/j.carres.2016.03.012

Cited by 6 publications

(4 citation statements)

References 25 publications

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“…The 1,2- cis linkage was confirmed by the 1 H NMR signal at δ 5.27 (H-1′) and the 13 C NMR signal at δ 92.3 (C-1′) with J CH 167.5 Hz. However, due to the high reactivity of the trichloroacetimidate donor, formation of hemiacetal in a significant amount resulted in a low yield of the disaccharide, but the 1,2- cis linkage was formed exclusively.…”

Section: Resultsmentioning

confidence: 99%

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Chemical Synthesis of β-l-Rhamnose Containing the Pentasaccharide Repeating Unit of the O-Specific Polysaccharide from a Halophilic Bacterium Halomonas ventosae RU5S2EL in the Form of Its 2-Aminoethyl Glycoside

Pal

Mukhopadhyay

2021

J. Org. Chem.

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Total synthesis of the pentasaccharide repeating unit of the OPS from Halomonas ventosae RU5S2EL is accomplished through a [3+2] block strategy. Picoloyl-induced hydrogen-bond-assisted aglycon delivery (HAD) is used for two consecutive 1,2-cis-L-rhamnosylations, and remote participation is used for α-selective glucosylation. The choice of 2aminoethyl glycoside at the reducing end is opted for, leaving the scope for further glycoconjugate formation without hampering the reducing-end stereochemistry.

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Section: Resultsmentioning

confidence: 99%

“…5 Hz. However, due to the high reactivity 27 of the trichloroacetimidate donor, formation of hemiacetal in a significant amount resulted in a low yield 28 of the disaccharide, but the 1,2-cis linkage was formed exclusively.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Chemical Synthesis of β-l-Rhamnose Containing the Pentasaccharide Repeating Unit of the O-Specific Polysaccharide from a Halophilic Bacterium Halomonas ventosae RU5S2EL in the Form of Its 2-Aminoethyl Glycoside

Pal

Mukhopadhyay

2021

J. Org. Chem.

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“…There have been many efforts towards the chemical synthesis of oligosaccharides for homogeneous vaccine development against priority pathogens including Staphylococcus aureus , Streptococcus pneumoniae , Hemophilus influenzae b and Shigella [ 38 , 39 , 40 , 41 , 42 , 43 , 44 ]. In this section, we describe some of the advances in the chemoenzymatic/enzymatic synthesis of oligosaccharides from select WHO priority pathogens.…”

Section: Enzymatic Synthesis Of Oligosaccharides From Antibiotic-resistant Bacteriamentioning

confidence: 99%

Recent and Future Advances in the Chemoenzymatic Synthesis of Homogeneous Glycans for Bacterial Glycoconjugate Vaccine Development

Adegbite

McCarthy

2021

Vaccines

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Vaccines are important in preventing disease outbreaks and controlling the spread of disease in a population. A variety of vaccines exist, including subunit, recombinant, and conjugate vaccines. Glycoconjugate vaccines have been an important tool to fight against diseases caused by a number of bacteria. Glycoconjugate vaccines are often heterogeneous. Vaccines of the future are becoming more rationally designed to have a defined oligosaccharide chain length and position of conjugation. Homogenous vaccines could play an important role in assessing the relationship between vaccine structure and immune response. This review focuses on recent advances in the chemoenzymatic production of defined bacterial oligosaccharides for vaccine development with a focus on Neisseria meningitidis and selected WHO-prioritized antibacterial resistant-pathogens. We also provide some perspective on future advances in the chemoenzymatic synthesis of well-defined oligosaccharides.

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“…The openings of benzylidene acetals moieties are often made by reducing reaction with a Lewis acid/hydride couple. The nature of the reducing / Lewis acid couple and that of the sugar considerably influence the regioselectivity of the reduction, i.e., the ratio (6-OBn / 4-OBn) [5][6][7][8][9] .…”

Section: Introductionmentioning

confidence: 99%

Regioselective reduction of benzylidene acetals from a bis-heterocyclic pyrimidino-pyranoside platform

Samb¹,

Gaye²

2021

Mediterr.J.Chem.,

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Linear synthesis of the hexasaccharide related to the repeating unit of the O-antigen from Shigella flexneri serotype 1d (I: 7,8)

Cited by 6 publications

References 25 publications

Chemical Synthesis of β-l-Rhamnose Containing the Pentasaccharide Repeating Unit of the O-Specific Polysaccharide from a Halophilic Bacterium Halomonas ventosae RU5S2EL in the Form of Its 2-Aminoethyl Glycoside

Chemical Synthesis of β-l-Rhamnose Containing the Pentasaccharide Repeating Unit of the O-Specific Polysaccharide from a Halophilic Bacterium Halomonas ventosae RU5S2EL in the Form of Its 2-Aminoethyl Glycoside

Recent and Future Advances in the Chemoenzymatic Synthesis of Homogeneous Glycans for Bacterial Glycoconjugate Vaccine Development

Regioselective reduction of benzylidene acetals from a bis-heterocyclic pyrimidino-pyranoside platform

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