Methanolysis of 7-Acetoxy-4-Methylcoumarin Catalyzed by Cyclosophoraoses Isolated from Rhizobium meliloti

Park, Hey-Lin; Kang, Lin‐Woo; Jung, Seunho

doi:10.5012/bkcs.2008.29.1.228

Bulletin of the Korean Chemical Society

2008

DOI: 10.5012/bkcs.2008.29.1.228

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Methanolysis of 7-Acetoxy-4-Methylcoumarin Catalyzed by Cyclosophoraoses Isolated from Rhizobium meliloti

Hey-Lin Park¹,

Lin‐Woo Kang²,

Seunho Jung

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Cited by 7 publications

References 19 publications

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, 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 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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Enhanced solubility of galangin based on the complexation with methylated microbial cyclosophoraoses

Kim

Choi

et al. 2013

J Incl Phenom Macrocycl Chem

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Methylated cyclosophoraoses (M-Cys) were synthesized by reaction using dimethyl sulfate with native Cys (unbranched cyclic b-1,2-D-glucans) isolated from Rhizobium leguminosarum biovar viciae VF-39. Its structure was proven using nuclear magnetic resonance ( 1 H NMR) spectroscopy, Fourier-transform infrared (FT-IR) spectroscopy, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Based on the enhanced hydrophobicity by methylation of Cys, we investigated the inclusion property with the water-insoluble flavonoid, galangin, through a phase solubility study using ultraviolet-visible spectroscopy. The solubility of galangin was enhanced 5.6-fold according to the added concentrations (1 mM) of M-Cys, compared to the 1.9-fold and 3.4-fold enhancements by b-Cyclodextrin (b-CD) and heptakis (2,6-di-O-methyl)-b-cyclodextrin (DM-b-CD), respectively. M-Cys was also shown to have the highest binding constant (5,534 M -1 ) with galangin among the tested host molecules (b-CD, DM-b-CD, Cys, and M-Cys). From this result, we can infer that the complex of galangin with M-Cys is more stable than any of the other host molecules. The continuous variation method showed that the galangin/M-Cys complex was suitable for 1:1 stoichiometry. The formation of the complex was confirmed with 1 H NMR, FT-IR, differential scanning calorimetry, and scanning electron microscopy. Furthermore, the hypothetical molecular model of 1:1 galangin/M-Cys complex was suggested by molecular docking simulations. The cytotoxicity to the human cervical adenocarcinoma cell lines was enhanced by the galangin/M-Cys complex compared with free galangin. The obtained results indicate that M-Cys can be utilized as an effective complexing agent for galangin.

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Properties and current applications of bacterial cyclic β-glucans and their derivatives

Cho

Jeong

Choi

et al. 2016

J Incl Phenom Macrocycl Chem

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Cyclic b-glucans are unique constituents that are found in the periplasmic space and extracellular media of Agrobacterium, Rhizobium, Bradyrhizobium, Rhodobacter, Xanthomonas, and Ralstonia species. Based on their glycosidic linkages, they are classified into three groups composed of cyclic b-(1,2), b-(1,3)-b-(1,6), and b-(1,2)-a-(1,6) linked glucans. Their degrees of polymerization vary ranging from 10 to 40 glucose residues, and the backbone structure can be modified with non-sugar moieties. Since the macrocyclic oligosaccharides possess their own characteristics such as inherent three-dimensional structures, hydrogen bonding, and complex-forming abilities, various possible applications would be of interest in the field of green chemistry, separation science, pharmaceutical, and food industries. In this review, we have addressed the properties and current applications of bio-sourced cyclic bglucans and their derivatives.

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Methanolysis of 7-Acetoxy-4-Methylcoumarin Catalyzed by Cyclosophoraoses Isolated from Rhizobium meliloti

Cited by 7 publications

References 19 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Enhanced solubility of galangin based on the complexation with methylated microbial cyclosophoraoses

Properties and current applications of bacterial cyclic β-glucans and their derivatives

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