Synthesis and characterization of carboxymethylated cyclosophoraose, and its inclusion complexation behavior

Lee, Sanghoo; Park, Heylin; Seo, Donghyuk; Choi, Youngjin; Jung, Seunho

doi:10.1016/j.carres.2003.11.011

Cited by 25 publications

(8 citation statements)

References 22 publications

(9 reference statements)

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“…Most derivatizations have been carried out using cyclic b-(1,2) glucans and the related information is summarized in Table 1. For the anionic contribution, carboxymethylation was carried out using monochloroacetic acid in alkaline conditions, and the cyclic b-(1,2) glucans were substituted with carboxymethyl groups at C4 and 6 positions of glucose with DS ranging from 0.012 to 0.290 [95][96][97]. Sulfated cyclic b-(1,2) glucans were synthesized from a reaction of cyclic b-(1,2) glucans and sulfur trioxide trimethylamine complex in dimethylformamide at 60-70°C for 24 h [98].…”

Section: Natural and Chemical Derivatizationmentioning

confidence: 99%

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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Section: Natural and Chemical Derivatizationmentioning

confidence: 99%

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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“…The molecules are shaped such as a distorted and flexible ring, and the possibility of a different molecular mechanism for the complexation from the typical inclusion complexation by CD was suggested [60,61]. They could also be substituted by various functional groups including carboxymethyl, hydroxypropyl, sulfated, or methyl groups (Figure 1f) [62,63,64,65]. CyS oligomers were also designed (Figure 1g), and the cooperative complexation enhanced solubility and bioavailability of fisetin [66].…”

Section: Oligosaccharidesmentioning

confidence: 99%

Supramolecular Complexation of Carbohydrates for the Bioavailability Enhancement of Poorly Soluble Drugs

Cho

Jung

2015

Molecules

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Abstract:In this review, a comprehensive overview of advances in the supramolecular complexes of carbohydrates and poorly soluble drugs is presented. Through the complexation process, poorly soluble drugs could be efficiently delivered to their desired destinations. Carbohydrates, the most abundant biomolecules, have diverse physicochemical properties owing to their inherent three-dimensional structures, hydrogen bonding, and molecular recognition abilities. In this regard, oligosaccharides and their derivatives have been utilized for the bioavailability enhancement of hydrophobic drugs via increasing the solubility or stability. By extension, polysaccharides and their derivatives can form self-assembled architectures with poorly soluble drugs and have shown increased bioavailability in terms of the sustained or controlled drug release. These supramolecular systems using carbohydrate will be developed consistently in the field of pharmaceutical and medical application.

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“…MALDI analysis of several of the reaction intermediates showed acylated cyclosophoraoses in the mass range 3,000-4,500. Carboxymethylated Cys from R. leguminosarum biovar trifolii could be used to complex and, consequently increase the aqueous solubility of hydrobenzoin and N-acetyltryptophan (Lee et al, 2004c).…”

Section: Carbohydrates As Synthetic Reagentsmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2003–2004

Harvey

2008

Mass Spectrometry Reviews

100

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This review is the third update of the original review, published in 1999, on the application of matrix-assisted laser desorption/ionization (MALDI) mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings the topic to the end of 2004. Both fundamental studies and applications are covered. The main topics include methodological developments, matrices, fragmentation of carbohydrates and applications to large polymeric carbohydrates from plants, glycans from glycoproteins and those from various glycolipids. Other topics include the use of MALDI MS to study enzymes related to carbohydrate biosynthesis and degradation, its use in industrial processes, particularly biopharmaceuticals and its use to monitor products of chemical synthesis where glycodendrimers and carbohydrate-protein complexes are highlighted.

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Synthesis and characterization of carboxymethylated cyclosophoraose, and its inclusion complexation behavior

Cited by 25 publications

References 22 publications

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

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

Supramolecular Complexation of Carbohydrates for the Bioavailability Enhancement of Poorly Soluble Drugs

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2003–2004

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