13133-07-8Relevant articles and documents
Continuous production of fructooligosaccharides and invert sugar by chitosan immobilized enzymes: Comparison between in fluidized and packed bed reactors
Lorenzoni, André S.G.,Aydos, Luiza F.,Klein, Manuela P.,Ayub, Marco A.Z.,Rodrigues, Rafael C.,Hertz, Plinho F.
, p. 51 - 55 (2015)
In this work, β-fructofuranosidase and β-fructosyltransferase were covalently immobilized on chitosan spheres, using glutaraldehyde as a coupling agent, in order to produce invert sugar and fructooligosaccharides (FOS). Maxinvert L was used to make β-fructofuranosidase biocatalyst yielding 7000 HU/g. A partial purified β-fructosyltransferase from Viscozyme L was used to prepare the other biocatalyst yielding 2100 TU/g. The production of invert sugar and FOS was evaluated using different continuous enzymatic reactors: two packed bed reactors (PBR) and two fluidized bed reactors (FBR). The invert sugar production achieved a yield of 98% (grams of product per grams of initial sucrose) in the PBR and 94% in the FBR, whereas FOS production achieved a yield of 59% in the PBR and 54% in the FBR. It was also observed in both cases that varying the flow rate it is possible to modulate the FOS composition in terms of nystose and kestose concentrations. The operational stability of FOS produced in the PBR was evaluated for 40 days showing no reductions in yields.
Isolation and structural confirmation of the oligosaccharides containing α-d-fructofuranoside linkages isolated from fermented beverage of plant extracts
Okada, Hideki,Fukushi, Eri,Yamamori, Akira,Kawazoe, Naoki,Onodera, Shuichi,Kawabata, Jun,Shiomi, Norio
, p. 2633 - 2637 (2011)
Fermented beverage of plant extracts was prepared from the extracts of approximately 50 types of vegetables and fruits. Natural fermentation was carried out mainly by lactic acid bacteria (Leuconostoc spp.) and yeast (Zygosaccharomyces spp. and Pichia spp.). Two oligosaccharides containing an α-fructofuranoside linkage were detected in this beverage and isolated using carbon-Celite column chromatography and preparative HPLC. The structural confirmation of the saccharides was determined by methylation analysis, MALDI-TOF-MS, and NMR measurements. These saccharides were identified as α-d-fructofuranosyl-(2→6)-d-glucopyranose, which was isolated from a natural source for the first time, and a novel saccharide β-d- fructopyranosyl-(2→6)-α-d-fructofuranosyl-(2?1) -α-d-glucopyranoside.
Physicochemical characterization of fructooligosaccharides and evaluation of their suitability as a potential sweetener for diabetics
Mabel,Sangeetha,Platel, Kalpana,Srinivasan,Prapulla
, p. 56 - 66 (2008)
Fructooligosaccharides (FOSs) were prepared from sucrose using fungal fructosyl transferase (FTase) obtained from Aspergillus oryzae MTCC 5154. The resulting mixture consisted of glucose (28-30%), sucrose (18-20%) and fructooligosaccharides (50-54%) as indicated by HPLC analysis. Identification of oligomers present in the mixture of fructooligosaccharides was carried out using NMR spectroscopy and LC-MS. No compounds other than mono-, di-, tri-, tetra- and pentasaccharides were identified in the FOS mixture prepared using FTase. NMR and LC-MS spectra proved the absence of any toxic microbial metabolites of Aspergillus species in FOS thereby emphasizing its safe use as a food ingredient. Animal studies conducted on streptozotocin-induced diabetic rats suggested that the use of FOS as an alternative non-nutrient sweetener is without any adverse effects on various diabetes-related metabolic parameters. Despite the high free-sugar content associated with it, FOS did not further aggravate the hyperglycemia and glucosuria in diabetic animals, even at 10% levels. On the other hand, by virtue of its soluble fibre effect, it has even alleviated diabetic-related metabolic complications to a certain degree.
Separation and purification of fructo-oligosaccharide by high-speed counter-current chromatography coupled with precolumn derivatization
Duan, Wenjuan,Ji, Wenhua,Wei, Yuanan,Zhao, Ruixuan,Chen, Zijian,Geng, Yanling,Jing, Feng,Wang, Xiao
, (2018)
High-speed counter-current chromatography (HSCCC) coupled with precolumn derivatization was developed for isolating and purifying fructo-oligosaccharides (FOSs). Firstly, the total FOSs were precolumn derivatized and then separated by high-speed counter-current chromatography (HSCCC) with two-phase solvent system petroleum ether-n-butanol-methanol-water (3:2:1:4, v/v). Secondly, the obtained compounds were deacetylated and the fructo-oligosaccharides (FOSs) with high purity were obtained. Their structures were identified by mass spectrometry (MS) and nuclear magnetic resonance (NMR). This research successfully established a novel strategy for separation and purification of FOS. There is no doubt that the application of the research will be beneficial for the quantitative and qualitative analysis of products containing FOSs.
Inulinase immobilisation in PAA/PEG composite for efficient fructooligosaccharides production
Dimitrovski, Darko,Krastanov, Albert,Temkov, Mishela,Velickova, Elena
, (2020)
Inulinase was immobilised by entrapment method in polyacrylamide/polyethylene glycol composite and evaluated for its efficiency for short-chain fructooligosaccharides (3–6 degrees of polymerisation) production in batch hydrolysis system. Aqueous two-phase
Two novel oligosaccharides formed by 1F-fructosyltransferase purified from roots of asparagus (Asparagus officinalis L.)
Yamamori, Akira,Onodera, Shuichi,Kikuchi, Masanori,Shiomi, Norio
, p. 1419 - 1422 (2002)
Two novel oligosaccharides, tetra-and penta-saccharides were synthesized by fructosyl transfer from 1-kestose to 4G-β-D- galactopyranosylsucrose with a purified 1F-fructosyltransferase of asparagus roots and identified as 1F-β-D-fructofuranosyl-4 G-β-D-galactopyranosylsucrose, O-β-D-fructofuranosyl-(2 → 1)-β-D-fructofuranosyl-O-[β-D-galactopyranosyl-(1 → 4)]-α-D-glucopyranoside and 1F(1-β-D-fructofuranosyl) 2-4G-β-D-galactopyranosylsucrose, [O-β-D-fructofuranosyl-(2 → 1)]2-β-D-fructofuranosyl- O-[β-D-galactopyranosyl-(1 → 4)]-α-D-glucopyranoside, respectively. Both oligosaccharides were scarcely hydrolyzed by carbohydrase from rat small intestine. Human intestinal bacterial growth by 1 F-/β-D-fructofuranosyl-4G-β-D- galactopyranosylsucrose was compared with that by the tetrasaccharides, stachyose and nystose. Bifidobacteria utilized 1F-β-D- fructofuranosyl-4G-β-D-galactopyranosylsucrose to the same extent as stachyose or nystose. On the other hand, the unfavorable bacteria, Clostridium perfringens, Escherichia coli and Enterococcus faecalis, that produce mutagenic substances did not use the synthetic oligosaccharide.
Molecular insight into regioselectivity of transfructosylation catalyzed by GH68 levansucrase and β-fructofuranosidase
Kikuchi, Asako,Kimura, Atsuo,Lang, Weeranuch,Okuyama, Masayuki,Sadahiro, Juri,Serizawa, Ryo,Tagami, Takayoshi,Tanuma, Masanari
, (2021)
Glycoside hydrolase family 68 (GH68) enzymes catalyze β-fructosyltransfer from sucrose to another sucrose, the so-called transfructosylation. Although regioselectivity of transfructosylation is divergent in GH68 enzymes, there is insufficient information available on the structural factor(s) involved in the selectivity. Here, we found two GH68 enzymes, β-fructofuranosidase (FFZm) and levansucrase (LSZm), encoded tandemly in the genome of Zymomonas mobilis, displayed different selectivity: FFZm catalyzed the β-(2→1)-transfructosylation (1-TF), whereas LSZm did both of 1-TF and β-(2→6)-transfructosylation (6-TF). We identified His79FFZm and Ala343FFZm and their corresponding Asn84LSZm and Ser345LSZm respectively as the structural factors for those regioselectivities. LSZm with the respective substitution of FFZm-type His and Ala for its Asn84LSZm and Ser345LSZm (N84H/S345A-LSZm) lost 6-TF and enhanced 1-TF. Conversely, the LSZm-type replacement of His79FFZm and Ala343FFZm in FFZm (H79N/A343SFFZm) almost lost 1-TF and acquired 6-TF. H79N/A343S-FFZm exhibited the selectivity like LSZm but did not produce the β-(2→6)-fructoside-linked levan and/or long levanooligosaccharides that LSZm did. We assumed Phe189LSZm to be a responsible residue for the elongation of levan chain in LSZm and mutated the corresponding Leu187FFZm in FFZm to Phe. An H79N/L187F/A343S-FFZm produced a higher quantity of long levanooligosaccharides than H79N/A343S-FFZm (or H79NFFZm), although without levan formation, suggesting that LSZm has another structural factor for levan production. We also found that FFZm generated a sucrose analog, β-D-fructofuranosyl α-D-mannopyranoside, by β-fructosyltransfer to D-mannose and regarded His79FFZm and Ala343FFZm as key residues for this acceptor specificity. In summary, this study provides insight into the structural factors of regioselectivity and acceptor specificity in transfructosylation of GH68 enzymes.
A high-speed countercurrent chromatography for preparing high-purity kestose chitosan monomer
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Paragraph 0038-0042, (2017/09/26)
The invention discloses a method for preparing high-purity sucrose fructan monomers by high-speed counter-current chromatography, which comprises the following steps: protecting hydroxyl of fructooligosaccharide to obtain fructooligosaccharide derivatives, carrying out high-speed counter-current chromatography to separate the fructooligosaccharide derivatives to obtain a kestose derivative, a nystose derivative and a glucopyranoside derivative, removing the hydroxyl protecting group to obtain the high-purity kestose, nystose and glucopyranoside. The purities of the kestose, nystose and glucopyranoside are respectively higher than 98%. The method has the advantages of short separation time, high preparation quantity,, high recovery rate, no sample loss, mild separation environment and solvent saving, and can implement scale-up production.
