Synthesis of a trisaccharide repeating unit of the O-antigen from Burkholderia anthina and its dimer

Geng, Xueyun; Wang, Lizhen; Gu, Guofeng; Guo, Zhongwu

doi:10.1016/j.carres.2016.03.023

Cited by 10 publications

(1 citation statement)

References 55 publications

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“…Glycosylation of the known GlcNPhth acceptor 2 [12] and the rhamnosyl donor 3 [13] through the activation of thioglycoside using N -iodosuccinimide (NIS) in the presence of TMSOTf gave the Rha-(1→3)-GlcNPhth disaccharide 4 in 84% yield. The presence of a participating acetate group at the 2-position of the rhamnosyl donor 3 ensured the formation of the desired 1,2- trans glycoside.…”

Section: Resultsmentioning

confidence: 99%

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

Pal¹,

Mukhopadhyay²

2019

Beilstein J. Org. Chem.

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The total chemical synthesis of the pentasaccharide repeating unit of the O-polysaccharide from E. coli O132 is accomplished in the form of its 2-aminoethyl glycoside. The 2-aminoethyl glycoside is particularly important as it allows further glycoconjugate formation utilizing the terminal amine without affecting the stereochemistry of the reducing end. The target was achieved through a [3 + 2] strategy where the required monosaccharide building blocks are prepared from commercially available sugars through rational protecting group manipulation. The NIS-mediated activation of thioglycosides was used extensively for the glycosylation reactions throughout.

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Section: Resultsmentioning

confidence: 99%

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

Pal¹,

Mukhopadhyay²

2019

Beilstein J. Org. Chem.

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Regioselective Protection at the Secondary Positions of Carbohydrates with Acyclic Protecting Groups

Goekjian

Vidal

2018

Protecting Groups

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Analysis of Carbohydrates and Glycoconjugates by Matrix‐assisted Laser Desorption/Ionization Mass Spectrometry: An Update for 2015–2016

Harvey

2021

Mass Spectrometry Reviews

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This review is the ninth update of the original article published in 1999 on the application of matrix‐assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2016. Also included are papers that describe methods appropriate to analysis by MALDI, such as sample preparation techniques, even though the ionization method is not MALDI. Topics covered in the first part of the review include general aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, fragmentation and arrays. The second part of the review is devoted to applications to various structural types such as oligo‐ and poly‐saccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals. Much of this material is presented in tabular form. The third part of the review covers medical and industrial applications of the technique, studies of enzyme reactions and applications to chemical synthesis. The reported work shows increasing use of combined new techniques such as ion mobility and the enormous impact that MALDI imaging is having. MALDI, although invented over 30 years ago is still an ideal technique for carbohydrate analysis and advancements in the technique and range of applications show no sign of deminishing. © 2020 Wiley Periodicals, Inc.

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Synthesis of a trisaccharide repeating unit of the O-antigen from Burkholderia anthina and its dimer

Cited by 10 publications

References 55 publications

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

Regioselective Protection at the Secondary Positions of Carbohydrates with Acyclic Protecting Groups

Analysis of Carbohydrates and Glycoconjugates by Matrix‐assisted Laser Desorption/Ionization Mass Spectrometry: An Update for 2015–2016

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