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A new process based on enzymatic synthesis of a series of raffinose-derived oligosaccharides or raffinosyl-oligofructosides (RFOS) with degree of polymerization (DP) from 4 to 8 was developed in the presence of raffinose. This process involves a transfructosylation reaction catalyzed by an inulosucrase from Lactobacillus gasseri DSM 20604 (IS). The main synthesized RFOS were structurally characterized by Nuclear Magnetic Resonance (NMR). According to the elucidated structures, RFOS consist of β-2,1-linked fructose unit(s) to raffinose: α-D-galactopyranosyl-(1→6)-α-Dglucopyranosyl-(1↔2)-β-D-fructofuranosyl-((1←2)-β-D-fructofuranoside)n (where n refers to the number of transferred fructose moieties). The maximum yield of RFOS was 33.4% (in weight respect to the initial amount of raffinose) and was obtained at the time interval of 8-24 h of transfructosylation reaction initiated with 50% (w/v) of raffinose. Results revealed the high acceptor and donor affinity of IS towards raffinose, being fairly comparable to that of sucrose for the production of fructooligosaccharides (FOS), including when both carbohydrates coexisted (sucrose:raffinose mixture, 250 g L -1 each). The production of RFOS was also attempted in the presence of sucrose:melibiose mixtures; in this case, the predominant acceptor-product formed was raffinose followed by a minor production of a series of oligosaccharides with varying DP. The easiness of RFOS synthesis and the structural similarities with both raffinose and fructan series of oligosaccharides warrant the further study of the potential bioactive properties of these unexplored oligosaccharides.

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Synthesis and structural characterization of raffinosyl-oligofructosides upon transfructosylation by Lactobacillus gasseri DSM 20604 inulosucrase

Díez-Municio

Herrero

Rivas

et al. 2016

Appl Microbiol Biotechnol

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Study of Influential Factors on Oligosaccharide Formation by Fructosyltransferase Activity during Stachyose Hydrolysis by Pectinex Ultra SP-L

Montilla

Olano

Martínez‐Villaluenga

et al. 2011

J. Agric. Food Chem.

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The influence of reaction conditions for oligosaccharide synthesis from stachyose using a commercial enzymatic preparation from Aspergillus aculeatus (Pectinex Ultra SP-L) was studied. Oligosaccharides were analyzed by gas chromatography with flame ionization detection (GC-FID) and matrix-assisted laser desorption/ionization-time-of-flight-mass spectrometry (MALDI-TOF-MS). Galactosyl-melibiose (DP(3)) was synthesized as a result of fructosidase activity, whereas fructosyl-stachyose (DP(5)) and difructosyl-stachyose (DP(6)) were formed as a consequence of the fructosyltransferase activity of Pectinex Ultra SP-L. The optimal reaction conditions for the synthesis of penta- and hexasaccharides were 60 °C, pH 5.5, 600 mg/mL stachyose, and 34 U/mL enzyme. Reaction time played an important role in oligosaccharide mixture composition constituted by 20% DP(5), 0.7% DP(6), 55% stachyose, 21% galactosyl-melibiose, and 1% monosaccharides after 1 h and 16% DP(5), 4% DP(6), 27% stachyose, 44% galactosyl-melibiose, and 2% monosaccharides after 3 h. In conclusion, stachyose could be used as a substrate for the enzymatic synthesis of new oligosaccharides that may open new opportunities in the development of future prebiotics.

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Identification of Oligosaccharides Formed during Stachyose Hydrolysis by Pectinex Ultra SP-L

Montilla

Corzo

Olano

et al. 2009

J. Agric. Food Chem.

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The commercial enzyme preparation Pectinex Ultra SP-L containing fructosyltransferase activity was used to hydrolyze stachyose. During this reaction, besides the formation of mono-, di-, and trisaccharides (DP(3)), the presence of one pentasaccharide (DP(5)) and a new oligosaccharide (DP(6)) has been detected by gas chromatography. DP(5) and DP(6) oligosaccharides were isolated and fully characterized for the first time by an extensive nuclear magnetic resonance (NMR) study. Complete structure elucidation and full proton and carbon assignments were carried out using 1D ((1)H, (13)C) and 2D (gCOSY, multiplicity-edited gHSQC, gHSQC-TOCSY, and gHMBC) NMR experiments. The two oligosaccharides were shown to be stachyose-based structures; the pentasaccharide has a fructose unit linked to the C-1 of the fructose end of stachyose, and the hexasaccharide has a fructose unit linked to the C-1 of the fructose end of the pentasaccharide. The fructosyltransferase activity present in Pectinex Ultra SP-L allows new uses of this commercial enzyme preparation in the synthesis of oligosaccharides derived from alpha-galactosides.

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Cited by 3 publications

References 2 publications

Synthesis and structural characterization of raffinosyl-oligofructosides upon transfructosylation by Lactobacillus gasseri DSM 20604 inulosucrase

Synthesis and structural characterization of raffinosyl-oligofructosides upon transfructosylation by Lactobacillus gasseri DSM 20604 inulosucrase

Study of Influential Factors on Oligosaccharide Formation by Fructosyltransferase Activity during Stachyose Hydrolysis by Pectinex Ultra SP-L

Identification of Oligosaccharides Formed during Stachyose Hydrolysis by Pectinex Ultra SP-L

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