Gas chromatographic determination of conjugated aldehydes in products of periodate oxidation of pyranose sugars as diethyl dithioacetals

Honda, Susumu; Fukuhara, Yoko; Kakehi, Kazuaki

doi:10.1021/ac50023a019

Cited by 24 publications

(2 citation statements)

References 14 publications

(23 reference statements)

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“…24 In this study, acidified DEAET was used as derivatization reagent instead of mercaptoethanesulfonate to introduce tertiary amine groups to monosaccharides. The reaction is almost quantitative when appropriate ratios of trifluoroacetic acid (TFA)/DEAET were used, as reported by Honda et al 25 The dithioacetals have no steric isomers because of the reaction at C-l asymmetric center. Larger amounts of by-products like monothioacetals were found when hydrochloric acid used as catalyst, while acetic acid can not produce dithioacetal.…”

Section: Derivatization Proceduresmentioning

confidence: 58%

Analysis of Monosaccharides by Capillary Electrophoresis with Electrochemiluminescence Detection

Lee

2007

ANAL. SCI.

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Carbohydrates play a very important role in the human life cycle and form the base of many foodstuffs. 1 As integral components of glycoproteins and glycolipids, carbohydrates are involved in many biological processes, such as cell recognition and the immune response. 2,3 Therefore, carbohydrate analysis is still of great interest.Various direct detection methods have been reported for carbohydrate combined with separation techniques, including flame ionization detection, 4 mass spectroscopy detection, 5 refractive index, 6 indirect UV (or fluorescence) 7,8 and pulsed amperometric detection 9 for gas chromatography, high performance liquid chromatography (HPLC), ion chromatography and capillary electrophoresis (CE). Because carbohydrates lack chromophores (or fluorophores) to facilitate the sensitive detection with UV (or fluorescence) detection, derivatization has most widely been used for carbohydrate analysis. A number of methods were reported based on reductive amination with various chromophores (fluorophores): aminobenzoic acid (AA), 10 8-aminonaphthalene-1,3,6-trisulfonate (ANTS), 11 dansylhydrazine (DHZ), 12 and 9-aminoacridone (AMAC). 13 A direct chemiluminophore derivatization method was also reported using 3-aminophthalhydrazide (APH) for the analysis of monosaccharides. 14 Recently, tris(2,2′-bipyridyl)ruthenium(II) [Ru(bpy)3 3+ ]-based electrogenerated chemiluminescence (ECL) detection has been widely studied because it provides an extremely sensitive means of detection. Many works were reported for the assays of amino acids, proteins, amines, drugs with the combination of HPLC and CE separation techniques. [15][16][17][18][19][20][21] In this study, we investigate the CE-ECL method for the analysis of four monosaccharides, which usually closely positioned in CE electropherograms, using 2-diethylaminoethanethiol (DEAET) as a derivatization reagent. Experimental Reagents and chemicalsTris(2,2′-bipyridyl)dichlororuthenium (II) ) were all HPLC grade. All buffer solutions were prepared with water purified in a Milli-Q System (Millipore, Beford, MA, USA). The standard solutions of monosaccharides were prepared with methanol and stored in a refrigerator at 4˚C. ApparatusA CE system was assembled in the laboratory. A Spellman CZE 1000R (Plainview, NY, USA) was used for electrophoresis and electrokinetic injection. A 25-μm i.d. 90-cm long uncoated fused-silica capillary (Polymicro Technologies, Phoenix, AZ, USA) was used for the CE column. The detection cell used in this study was similar to that described elsewhere. 22 A Pt working electrode (1.0 mm in diameter), a Pt wire counter electrode (1 mm in diameter) and a Ag/AgCl reference electrode were used in a conventional three-electrode system. The distance from the capillary end to working electrode surface was set at 100 μm by a microcontroller. Controlled potential electrolysis for Ru(bpy)3 2+ oxidation was carried out with a BAS-Epsilon (West Lafayette, IN, USA) electrochemical analyzer. The ECL light was captured by a Hamamatsu Photonics R238 photomult...

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Section: Derivatization Proceduresmentioning

confidence: 58%

Analysis of Monosaccharides by Capillary Electrophoresis with Electrochemiluminescence Detection

Lee

2007

ANAL. SCI.

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“…This micro-method can be used for the determination of interglycosidic linkage in oligosaccharides, and for making detailed studies on the mechanism of periodate oxidation [190].…”

Section: Chromatographic Methods Of Analysismentioning

confidence: 99%

Periodate oxidation and its contribution to instrumental methods of micro-analysis—A review

Vlessidis

Evmiridis

2009

Analytica Chimica Acta

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Miscellaneous applications with immobilized enzyme reactors

Takeuchi¹,

Hobo²

1994

Analytical Applications of Immobilized Enzyme Reactors

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Gas chromatographic determination of conjugated aldehydes in products of periodate oxidation of pyranose sugars as diethyl dithioacetals

Cited by 24 publications

References 14 publications

Analysis of Monosaccharides by Capillary Electrophoresis with Electrochemiluminescence Detection

Analysis of Monosaccharides by Capillary Electrophoresis with Electrochemiluminescence Detection

Periodate oxidation and its contribution to instrumental methods of micro-analysis—A review

Miscellaneous applications with immobilized enzyme reactors

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