Convenient assembly of trimeric Lex determinants using carbosilane scaffolds by means of Huisgen cycloaddition

Matsuoka, Koji; Yamaguchi, Hiroki; Kohzu, Tatsuya; Sakamoto, Junichi; Koyama, Tetsuo; Hatano, Ken; Yamamoto, Sadaki; Mori, T.; Hatanaka, Kenichi

doi:10.1016/j.tetlet.2012.10.004

Cited by 6 publications

(1 citation statement)

References 37 publications

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“…The utilization of 4-(chloromethyl)styrene 1 (CM-Str) as a starting material for the preparation of a series of functionalized monomers was examined in order to construct polymeric bioprobe families. We previously reported a convenient synthesis of glycomonomers using CM-Str 1 as a starting material by means of the Huisgen cycloaddition reaction [ 20 , 21 , 22 , 23 ] and polymer syntheses [ 11 ]. In this paper, alternative preparations of a glycomonomer and other useful functional monomers are described.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis

et al. 2018

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CM-Str (4-(Chloromethyl)styrene) was used as a useful starting material for the construction of a series of functional monomers. Substitution of the chlorine to the corresponding azide was performed, and the reduction of the azide proceeded smoothly to afford an aminostyrene, which was used as a common precursor for the preparation of functional monomers. Condensation of the amine with a fluorophore, biotin and carbohydrate was accomplished. Among the monomers, a carbohydrate monomer was polymerized with or without acrylamide as a model polymerization to yield the corresponding water-soluble glycopolymers, and biological evaluations of the glycopolymers for a lectin, and wheat germ agglutinin (WGA), were carried out on the basis of the fluorescence change of tryptophan in the WGA.

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Section: Resultsmentioning

confidence: 99%

Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis

et al. 2018

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

Harvey

2015

Mass Spectrometry Reviews

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This review is the seventh update of the original article published in 1999 on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2012. General aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, and fragmentation are covered in the first part of the review and applications to various structural types constitute the remainder. The main groups of compound are oligo- and poly-saccharides, glycoproteins, glycolipids, glycosides, and biopharmaceuticals. Much of this material is presented in tabular form. Also discussed are medical and industrial applications of the technique, studies of enzyme reactions, and applications to chemical synthesis. © 2015 Wiley Periodicals, Inc. Mass Spec Rev 36:255-422, 2017.

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A constraint scaffold enhances affinity of a bivalent N-acetylglucosamine ligand against wheat germ agglutinin

Matsushita

Tsuchibuchi

Koyama

et al. 2018

Bioorganic & Medicinal Chemistry Letters

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Convenient assembly of trimeric Lex determinants using carbosilane scaffolds by means of Huisgen cycloaddition

Cited by 6 publications

References 37 publications

Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis

Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

A constraint scaffold enhances affinity of a bivalent N-acetylglucosamine ligand against wheat germ agglutinin

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