Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system

Zhao, Yuetao; Niu, Shan; Huang, Lu-bai; Wang, Jiming; Yin, Zhaojun; Li, Qing; Li, Zhongjun

doi:10.1016/j.tet.2013.03.094

Cited by 5 publications

(4 citation statements)

References 57 publications

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“…The mixture of stachyose and verbascose was further separated by Biogel P-2 gel filtration chromatography, due to the distinct difference in their molecular sizes. The data of MS and NMR (Figure 2) for the resulting fractions of verbascose clearly demonstrated that it was verbascose, 36 and the purity of verbascose obtained was 98.5% (Figure 1B).…”

Section: ■ Results and Discussionmentioning

confidence: 91%

“…It has been reported that mung bean (Phaseolus aureus), also known as green gram or golden gram that is commonly used in various cuisines across Asia, contains a high concentration of α-GOS, especially verbascose . As a kind of α-galacto-oligosaccharide, there are several papers available about verbascose composition, separation, synthesis, and structure analysis, − whereas information about the immunomodulatory and prebiotic effects of verbascose is not available. In this study, therefore, high-purity verbascose was prepared from mung bean by extraction and purification through column chromatography.…”

Section: Introductionmentioning

confidence: 99%

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Immunomodulatory Activity in Vitro and in Vivo of Verbascose from Mung Beans (Phaseolus aureus)

Dai

Zhang

et al. 2014

J. Agric. Food Chem.

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In the present study, the immunostimulatory activity of verbascose from mung beans (Phaseolus aureus) was evaluated by using in vitro cell models and in vivo animal models. The results of in vitro experiments showed that verbascose could enhance the ability of devouring neutral red of peritoneal macrophages and promote the release of nitric oxide and immune reactive molecules such as interleukin (IL)-6, IL-1β, interferon (IFN)-α, and IFN-γ. Treatment with verbascose at a dose of 200 μg/mL exhibited the best effects. For assay in vivo, administration of verbascose at a medium dose of 90 mg/kg body weight could significantly increase the index of spleen, activity of lysozyme in spleen and serum, hemolysin level in serum, and swelling rate of earlap in the delayed type of hypersensitivity (DTH) of immunosuppressed mice. All of the results suggested that verbascose had potent immunostimulatory activity and could be explored as a potential natural immunomodulatory agent in functional foods.

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Section: ■ Results and Discussionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Immunomodulatory Activity in Vitro and in Vivo of Verbascose from Mung Beans (Phaseolus aureus)

Dai

Zhang

et al. 2014

J. Agric. Food Chem.

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“…The known compound 20 was treated with benzoyl chloride and pyridine in order to protect the 6‐OH with benzoyl ester and thus furnishing the final monosaccharide donor 21 in 86 % yield. Subsequently, the pentasaccharide acceptor 19 was coupled with the donor 21 in presence of NIS and H 2 SO 4 ‐silica at –55 °C to afford the desired hexasaccharide 22 in 78 % yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Convergent Synthesis of the Hexasaccharide Repeating Unit of the O‐Antigenic OPS of Escherichia coli O133

Mitra

Mukhopadhyay

2019

Eur J Org Chem

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Synthesis of the hexasaccharide repeating unit of the O‐antigen from E. coli O133 has been accomplished with rational protecting group manipulations on commercially available monosaccharides and stereoselective glycosylations through a convergent protocol. A late stage TEMPO mediated oxidation is used to install the required uronic acid moiety. Chloroacetate group is used extensively as a temporary protecting group.

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“…As a high value-added oligosaccharide, preparation of raffinose has gained both academic and commercial interests (9)(10)(11)(12)(13)(14). Despite catalytic synthesis of raffinose has been extensively investigated (15)(16)(17)(18)(19); however, this method still suffers a disadvantage of inadequate yield and as well generates useless by-products during the synthesis. Excluding sucrose, raffinose is probably the most widespread oligosaccharide in the plant world, especially abundant in the sugar beet and cotton seed (20), thus producing raffinose by extraction from biomass-based wastes like the sugar beet molasses (12,21,22) and cottonseed meal (9)(10)(11)(23)(24)(25) might be a more environmentally friendly and low-cost process.…”

Section: Introductionmentioning

confidence: 99%

Adsorption separation of raffinose from sucrose by activated carbon: Equilibrium, kinetics and dynamic breakthrough

Bao

Duan

Zhang

et al. 2016

Separation Science and Technology

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Separation of oligosaccharides with a varied number of monosaccharides is an important issue in the food chemistry. Raffinose, a functional oligosaccharide, has attracted increasing attentions due to its strong proliferative effect on bacteria. Industrially, cottonseed meal is an important resource for producing raffinose; however, raffinose extracted from the cottonseed meal contains a significant amount of sucrose that debases the raffinose's quality. In this work, an adsorptive separation of raffinose and sucrose on activated carbon was reported. Adsorption isotherms, adsorption kinetics, and dynamic column adsorption-desorption were investigated. The activated carbon chosen has a significantly higher adsorption capacity of raffinose (0.60~0.65 g/g) than sucrose (0.35~0.40 g/g) at the equilibrium concentration studied (~35 g/L) and temperature from Downloaded by [University of Leeds] at 21:22 04 June 2016A c c e p t e d M a n u s c r i p t 2 293 K to 333 K. Adsorption isotherms and kinetics were fitted by Freundlich isotherm model and pseudo-second-order model, respectively. The effect of flow-rate and initial feed concentration on the dynamic adsorption were investigated, meanwhile, the separation performance was further confirmed from the dynamic desorption using aqueous ethanol of 20% as eluant. Remarkably, raffinose with purity over 90% and recovery of 79.2% could be obtained by adsorption-desorption cycle using the aqueous feed solution containing 20 g/L of raffinose and 6 g/L of sucrose.

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Synthesis of raffinose family oligosaccharides by regioselective de-O-benzylation with Co2(CO)8/Et3SiH/CO system

Cited by 5 publications

References 57 publications

Immunomodulatory Activity in Vitro and in Vivo of Verbascose from Mung Beans (Phaseolus aureus)

Immunomodulatory Activity in Vitro and in Vivo of Verbascose from Mung Beans (Phaseolus aureus)

Convergent Synthesis of the Hexasaccharide Repeating Unit of the O‐Antigenic OPS of Escherichia coli O133

Adsorption separation of raffinose from sucrose by activated carbon: Equilibrium, kinetics and dynamic breakthrough

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