Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion

Nanami, Masahiro; Ando, Hiromune; Kawai, Yumiko; Koketsu, Mamoru; Ishihara, Hideharu

doi:10.1016/j.tetlet.2006.12.056

Cited by 37 publications

(22 citation statements)

References 16 publications

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“…To study fragmentation revealing linkage position and residue identity Quercetin-α -Dglucopyranosides TOF (DHB) Synthesis with glucansucrase from Leuconostoc mesenteroides (Moon, et al, 2007a) α-Selenoglycosides MALDI Alkyl and aryl, selenoglycosyl amino acids, selenodisaccharides (Nanami, et al, 2007) TOF Sugar-cholesterol conjugates GlcNAc, Man and Gal linked with PEG as gene delivery system Tris-phosphorylated ester of Me β-D-Xylp TOF By reaction with 5,5-dimethyl-2-chloro-1,3,2-dioxaphosphorinane (Pugashova, et al, 2008) ANALYSIS OF CARBOHYDRATES AND GLYCOCONJUGATES & (Naresh, et al, 2008) Fatty acid modified chitobiose TOF (DHB)…”

Section: Maldi Osw Saponinsmentioning

confidence: 99%

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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Section: Maldi Osw Saponinsmentioning

confidence: 99%

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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“…Selenoglycosides are prepared by several procedures that involve in situ production of an -anomeric selenolate anion which can be obtained from p-methylbenzoyl selenoglycoside [137], by zincmediated cleavage of diselenides and subsequent reaction with glycosyl bromides [138], by reaction of peracetylated chloro derivatives and phenylselenol [139], by azidolysis/selenoglycosidation of disaccharidic glycals [140], by the action of indium(I) iodide on diselenides [141], by reaction of the diglucopyranosyl diselenide with alkyl halide under reducing conditions [142] and from thiostannanes by reaction with Me 2 Sn(SePh) 2 . This method is also applicable to thioglycosides by reaction with Bu 2 Sn(SPh) 2 [143].…”

Section: Phenylselenoglycoside Methodsmentioning

confidence: 99%

Glycosylation Methods in Oligosaccharide Synthesis. Part 1

Robina¹,

Carmona²,

Vargas

2008

COS

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A review dealing with the general aspects of oligosaccharide synthesis including the recent advances in protecting group strategies and anomeric control for stereoselective glycosylations, focusing on the formation of 1,2-cis-glycosides, are presented. Recent examples of the intramolecular aglycon delivery approach and of the remote effect on the stereochemistry of the new glycosidic bond are considered. In this part, updated examples of the use of glycosyl halides, thioglycosides, sulfoxides and phenylselenides as glycosylating agents for oligosaccharide synthesis are also discussed.

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“…This type of sugars found application in disaccharide and oligosaccharide synthesis as glycosyl donors, where an arylselenyl group introduced at the anomeric position functions during glycosylation as a leaving group (Figure 3). Using similar synthesis methods, it is possible to obtain selenodisaccharides in which the bridging oxygen of the glycosidic bond is replaced by selenium (Figure 4), as it happened in Nanami et al experiment [239]; the first examples of the synthesized α-selenoglycosides that link to the carbon in the sugar ring were obtained. The Se-glycosidic bond is resistant to enzymatic hydrolysis; therefore, selenoglycosides can act as inhibitors of glycosidase enzymes [237,238].…”

Section: Se-glycosidesmentioning

confidence: 98%

“…Using similar synthesis methods, it is possible to obtain selenodisaccharides in which the bridging oxygen of the glycosidic bond is replaced by selenium (Figure 4), as it happened in Nanami et al experiment [239]; the first examples of the synthesized αselenoglycosides that link to the carbon in the sugar ring were obtained. Using similar synthesis methods, it is possible to obtain selenodisaccharides in which the bridging oxygen of the glycosidic bond is replaced by selenium (Figure 4), as it happened in Nanami et al experiment [239]; the first examples of the synthesized α-selenoglycosides that link to the carbon in the sugar ring were obtained. Most of selenoglycosides are obtained by chemical synthesis.…”

Section: Se-glycosidesmentioning

confidence: 98%

Selenium-Containing Polysaccharides—Structural Diversity, Biosynthesis, Chemical Modifications and Biological Activity

2021

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Selenosugars are a group of sugar derivatives of great structural diversity (e.g., molar masses, selenium oxidation state, and selenium binding), obtained as a result of biosynthesis, chemical modification of natural compounds, or chemical synthesis. Seleno-monosaccharides and disaccharides are known to be non-toxic products of the natural metabolism of selenium compounds in mammals. In the case of the selenium-containing polysaccharides of natural origin, their formation is also postulated as a form of detoxification of excess selenium in microorganisms, mushroom, and plants. The valency of selenium in selenium-containing polysaccharides can be: 0 (encapsulated nano-selenium), IV (selenites of polysaccharides), or II (selenoglycosides or selenium built into the sugar ring to replace oxygen). The great interest in Se-polysaccharides results from the expected synergy between selenium and polysaccharides. Several plant- and mushroom-derived polysaccharides are potent macromolecules with antitumor, immunomodulatory, antioxidant, and other biological properties. Selenium, a trace element of fundamental importance to human health, has been shown to possess several analogous functions. The mechanism by which selenium exerts anticancer and immunomodulatory activity differs from that of polysaccharide fractions, but a similar pharmacological effect suggests a possible synergy of these two agents. Various functions of Se-polysaccharides have been explored, including antitumor, immune-enhancement, antioxidant, antidiabetic, anti-inflammatory, hepatoprotective, and neuroprotective activities. Due to being non-toxic or much less toxic than inorganic selenium compounds, Se-polysaccharides are potential dietary supplements that could be used, e.g., in chemoprevention.

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Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion

Cited by 37 publications

References 16 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

Glycosylation Methods in Oligosaccharide Synthesis. Part 1

Selenium-Containing Polysaccharides—Structural Diversity, Biosynthesis, Chemical Modifications and Biological Activity

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