A Polymer-homologous Series of Sugar Acetates from the Acetolysis of Cellulose

Dickey, Edgar E.; Wolfrom, M. L.

doi:10.1021/ja01171a017

Cited by 51 publications

(11 citation statements)

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“…In the case of polysaccharides, this idea has not yet been fully exploited in view of the difficulty of obtaining good single crystals of oligomers. In the cellulose series, it is well known that acetylated oligomers crystallize easily (2). Furthermore cellulose acetate structures are known to be closely related to those of cellulose (3, 4).…”

Section: Introductionmentioning

confidence: 99%

Crystal structure of β-D-acetyl cellobiose, C₂₈H₃₈O₁₉

Leung¹,

Chanzy²,

Pérez³

et al. 1976

Can. J. Chem.

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. Can. J. Chern. 54,1365Chern. 54, (1976. The crystal structure of O-D-acetyl cellobiose was studied by X-ray crystallography. The crystal data are a = 31.814(4), b = 19.414(5), c = 5.614(1) A, space group P212121. Z = 4. The structure, solved by direct method, was refined by block-diagonal least-squares to a final R value of 0.075 for 2605 observed reflections. The molecular conformation involves 4C1 pyranose rings with glycosidic torsion angles corresponding to near maximum extension of the molecule. Substantial differences in conformational angles were observed between this molecule and the unacetylated counterpart. The molecules lie along the a-axis of the unit cell. Les angles de torsion glycosidiques sont tels que la molCcule est proche de son extension maximum. La comparaison de la conformation de cette molCcule avec son homologue non acitylk rCvkle de notables diffkrences au niveau des angles de torsion. Les mol6cules sont parallkles B I'axe cristallographique a de la maille cristalline.

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Section: Introductionmentioning

confidence: 99%

Crystal structure of β-D-acetyl cellobiose, C₂₈H₃₈O₁₉

Leung¹,

Chanzy²,

Pérez³

et al. 1976

Can. J. Chem.

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“…In a final step, this solution is transferred into an excess of ice-cold hexane in order to re-precipitate the acetylated cellooligosaccharides, which are dried in a vacuum oven to obtain a solid, pure form. Using this method, the DP of the isolated oligomers ranged from 1 to 6 [80,89]; a value of 7 has also been reported [90]. Oligomers of higher chain length are present in the product in very low amounts, if at all.…”

Section: Acetolysismentioning

confidence: 70%

“…The degradation of cellulose by applying a mixture of glacial acetic acid, acetic anhydride, and concentrated sulfuric acid was originally developed by Hess et al [82] in 1935 and then further explored in several publications, for example by Miller et al [83], Dickey and Wolfrom [89], Wolfrom and Dacons [90], and Wolfrom and Thompson [91]. The main product compounds of the hydrolysis are peracetylated cellooligosaccharides.…”

Section: Acetolysismentioning

confidence: 99%

“…Nevertheless, several methods exploiting different separation mechanisms have been developed during the last few decades. On a preparative Preparation and Analysis of Cello-and Xylooligosaccharides scale, the most commonly used techniques, according to the literature, are: (1) SEC on particulate polyacrylamide or crosslinked dextran gels [80,81,85,88,[124][125][126][127][128][129]; (2) partition/adsorption chromatography on charcoal, untreated charcoal-celite, or stearic-acid treated charcoal-celite columns [80,83,96] and on cellulose-based stationary phases [80,130]; (3) hydrophilic interaction chromatography (HILIC) and normal phase high-performance liquid chromatography (NP-HPLC) on silica gels, amino-bonded silica columns, or matrices with copolymer-bonded cyclodextrins [80,89,131,132]; and (4) ion exchange chromatography on cation exchange resins with sulfo-groups coupled with metal counter ions (e.g., Ca ) or hydronium ions [10,80,98,133]. For analytical purposes, especially for purity investigations on isolated fractions homogenous with respect to the DP, a variety of methods exist.…”

Section: Separation and Analysis Of Oligosaccharidesmentioning

confidence: 99%

“…Furthermore, Alpert [151] suggested the application of a novel stationary phase, in which ethanolamine is incorporated into a coating of polysuccinimide covalently bound to silica. Unmodified silica gel was successfully used for the separation of acetylated cellooligosaccharides in the middle of the past century [89]. In their comparative study of different cellooligosaccharide preparation and separation methods, Akpinar et al [80] also tested separation by normal phase chromatography on silica gel.…”

Section: Normal Phase Hplc and Hydrophilic Interactionmentioning

confidence: 99%

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Preparation and Analysis of Cello- and Xylooligosaccharides

Vejdovszky

Oberlerchner

Zweckmair

et al. 2015

Advances in Polymer Science

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This review provides a general overview of preparation, separation, and analytical methods for cello-and xylooligosaccharides. Arising as side-stream products of different biorefinery processes, these compounds have increasingly gained the interest of researchers and engineers in the last few decades. Beside their application as additives in the food, feed, and pharmaceutical industries, these oligomeric carbohydrates are of key importance as model compounds for studying the dependence of physicochemical properties on the degree of polymerization (DP). First, different preparation methods for mixtures of oligosaccharides with DPs between 1 and 30 are discussed. These methods include acetolysis, acid and enzymatic hydrolysis, and glycoside synthesis. Then, separation techniques, including size exclusion chromatography, normal phase and hydrophilic interaction chromatography, and chromatography on cation exchange resins, are presented. Analysis of oligosaccharides by different techniques is described.

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