Table 1.
Microbial glycoside hydrolase enzymes most frequently used for the synthesis of food bioactive oligosaccharides
| Synthesized Oligosaccharide | General structurea [main linkages] | Involved enzymes (EC number) | Enzyme Source (microorganism) | GH familyb | Sugar substrate (reaction type) | References |
|---|---|---|---|---|---|---|
| Fructo-oligosaccharides | (Fru)n-Glc [β(2→1), β(2→6)] | β-Fructofuranosidase (EC 3.2.1.26) Inulosucrase (EC 2.4.1.9) Levansucrase (EC 2.4.1.10) | Fungi (Aspergillus niger; A. japonicus; A. oryzae; Aureobasidium pullulans; Penicillium citrinum) Bacteria (Bacillus macerans; Zymomonas mobilis; Lactobacillus reuteri; Arthrobacter sp.) | 32, 68, 100 | Sucrose (transfructosylation) | Sangeetha et al., 2005 |
| Galacto-oligosaccharides | (Gal)n-Glc (Gal)n-Gal [β(1→3), β(1→4), β(1→6)] | β-Galactosidase (EC 3.2.1.23) | Fungi (A. oryzae; A. niger; A. aculeatus) Bacteria (Bacillus sp.; Streptococcus thermophilus; Lactobacillus acidophilus; L. reuteri; Bifidobacterium sp.) Yeast (Kluyveromyces lactis; K. marxianus; Saccharomyces fragilis; Cryptococcus laurentii) | 1, 2, 3, 35, 42, 50 | Lactose (transgalactosylation) | Panesar et al., 2006 |
| Torres et al., 2010 | ||||||
| Galacto-oligosaccharides derived from lactulose | (Gal)n-Fru (Gal)n-Gal (Gal)n-Fru-Gal [β(1→1), β(1→4), β(1→6)] | β-Galactosidase (EC 3.2.1.23) | Fungi (A. oryzae; A. aculeatus) Yeast (K. lactis) | 1, 2, 3, 35, 42, 50 | Lactulose (transgalactosylation) | Cardelle-Cobas et al., 2008 |
| Martínez-Villaluenga et al., 2008b | ||||||
| Lactosucrose | β-Gal-(1→4)-α-Glc-(1→2)-β-Fru | β-Fructofuranosidase (EC 3.2.1.26) Levansucrase (EC 2.4.1.10) or β-Galactosidase (EC 3.2.1.23) | Bacteria (Arthrobacter sp. K-1; Z. mobilis; Bacillus subtilis; B. natto; B. circulans) | 32, 68, 100 or 1, 2, 3, 35, 42, 50 | Lactose and sucrose (transfructosylation of lactose or transgalactosylation of sucrose) | Takahama et al., 1991 |
| Pilgrim et al., 2001 | ||||||
| Park et al., 2005 | ||||||
| Han et al., 2009 | ||||||
| Li et al., 2009 | ||||||
| Lactulosucrose | β-Gal-(1→4)-β-Fru-(2→1)-α-Glc | Dextransucrase (EC 2.4.1.5) | Bacteria (Leuconostoc mesenteroides) | 70 | Lactulose and sucrose (transglucosylation) | Díez-Municio et al., 2012a |
| 2-α-glucosyl-lactose | β-Gal-(1→4)-α-Glc-(2→1)-α-Glc | Dextransucrase (EC 2.4.1.5) | Bacteria (L. mesenteroides) | 70 | Lactose and sucrose (transglucosylation) | Díez-Municio et al., 2012b |
| Isomalto-oligosaccharides | (Glc)n [α(1→6)] | A) α-Amylase (EC 3.2.1.1) and Pullulanase (EC 3.2.1.41) B) α-Glucosidase (EC 3.2.1.20) | Fungi (Aspergillus sp.; Aureobasidium pullulans) Bacteria (Bacillus subtilis; B. licheniformis; B. stearothermophilus) | A) 13, 14, 57, 119 B) 4, 13, 31, 63, 97, 122 | Starch [hydrolysis (A) and transglucosylation (B)] | Casci and Rastall, 2006 |
| Goffin et al., 2011 | ||||||
| Gluco-oligosaccharides | (Glc)n [α(1→2), α(1→3), α(1→4), α(1→6)]. | Dextransucrase (EC 2.4.1.5) | Bacteria (L. mesenteroides; L. citreum) | 70 | Maltose and sucrose (transglucosylation) | Remaud et al., 1992 |
| Chung and Day, 2002 | ||||||
| Kim et al., 2014 | ||||||
| Gentio-oligosaccharides | (Glc)n [β(1→6)] | Glucan endo-1,6-β-glucosidase (EC 3.2.1.75) or β-Glucosidase (EC 3.2.1.21) | Fungi (Penicillium multicolor; A. oryzae) | 5, 30 or 1, 3, 5, 9, 30, 116 | Pustulan (hydrolysis) or Gentibiose (transglucosylation) | Fujimoto et al., 2009 |
| Qin et al., 2011 | ||||||
| Pectic-oligosaccharides | (GalA)n [α(1→4)] (GalA-Rha)n [α(1→2), α(1→4)] * GalA residues can be partially esterified and Rha units ramified. | Polygalacturonase (EC 3.2.1.15) Rhamnogalacturonan galacturonohydrolase (EC 3.2.1.173) Rhamnogalacturonan rhamnohydrolase (EC 3.2.1.174) | Fungi (Fusarium moniliforme; Aspergillus pulverulentus; A. aculeatus; Kluyveromyces fragilis) Bacteria (B. licheniformis) | 28 | Pectin (hydrolysis) | Spiro et al., 1993 |
| Olano-Martin et al., 2001 | ||||||
| Coenen et al., 2008 | ||||||
| Holck et al., 2011 | ||||||
| Xylo-oligosaccharides | (Xyl)n [β(1→4)] | Endo-1,4-β-xylanase (EC 3.2.1.8) β-Xylosidase (EC 3.2.1.37) | Fungi (Trichoderma sp.; A. oryzae) | 5, 8, 9, 10, 11, 12, 16, 26, 30, 43, 44, 51, 62 | Xylan (hydrolysis) | Casci and Rastall, 2006 |
| Maltosyl-fructosides | (Fru)n-Malt [β(2→1), β(2→6)] | Levansucrase (EC 2.4.1.10) Inulosucrase (EC 2.4.1.9) | Bacteria (B. subtilis; Lactobacillus gasseri) | 32, 68 | Maltose and sucrose (transfructosylation) | Canedo et al., (1999) |
| Díez-Municio et al., (2013b) |
a.
Glc, glucose; Fru, fructose; Gal, galactose; GalA, galacturonic acid; Rha, rhamnose; Xyl, xylose; Malt, maltose.
b.
According to CAZy database.