Synthesis of novel lactose-derived oligosaccharides by two-step enzymatic reactions and structural characterization of the oligomers
Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research interests. In this study, a strategy of two-step enzymatic reactions was designed to first synthesize galacto-oligosaccharide (GOS) from lactose by β-...
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| Published in | Food research international Vol. 208; p. 116177 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
01.05.2025
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| Abstract | Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research interests. In this study, a strategy of two-step enzymatic reactions was designed to first synthesize galacto-oligosaccharide (GOS) from lactose by β-galactosidase, and then the novel oligosaccharides were synthesized by inulosucrase (IS) using the obtained GOS and sucrose as the substrates. The recombinant IS was initially expressed by employing the IS gene from Lactobacillus gasseri DSM 20604. The appropriate synthesis conditions by the IS were determined as: reaction time of 12 h, the concentration of IS at 25 U/mL, GOS to sucrose ratio of 1:2, and the total substrate concentration of 500 g/L. Purification of the synthesized oligosaccharides in the reaction mixture was done by fermentation with Kluyveromyces lactis CICC 1773 to remove the carbohydrate by-products, and HPLC on an oligosaccharide column. The purified oligosaccharides, namely, Oligo-1, Oligo-2, and Oligo-3 were determined for their monosaccharide components to be galactose and glucose in the molar ratios of 0.230:0.770, 0.522:0.478 and 0.637:0.363, respectively. These three oligosaccharides had relative molecular masses of 666.18, 990.26, and 1314.43, corresponding to the degree of polymerization (DP) value of 4, DP6, and DP8, respectively. NMR spectroscopic studies of the oligosaccharides revealed a common branched structure consisting of three glucosides, one of which was linked with one (Oligo-1), three (Oligo-2) and five galactosides (Oligo-3), respectively. These lactose-derived oligosaccharides with the structural patterns that were not reported earlier represented novel potential prebiotic agents for use in functional foods.
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•Novel lactose-derived oligosaccharides (DP 4, 6, and 8) were synthesized by a two-step enzymatic method.•Inulosucrase gene from Lactobacillus gasseri DSM 20604 was expressed in Escherichia coli BL21(DE3).•Purification of oligosaccharides was done by yeast fermentation to remove carbohydrate by-products and HPLC.•The synthesized oligosaccharides with a specific branched structure were not reported earlier. |
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| AbstractList | Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research interests. In this study, a strategy of two-step enzymatic reactions was designed to first synthesize galacto-oligosaccharide (GOS) from lactose by β-galactosidase, and then the novel oligosaccharides were synthesized by inulosucrase (IS) using the obtained GOS and sucrose as the substrates. The recombinant IS was initially expressed by employing the IS gene from Lactobacillus gasseri DSM 20604. The appropriate synthesis conditions by the IS were determined as: reaction time of 12 h, the concentration of IS at 25 U/mL, GOS to sucrose ratio of 1:2, and the total substrate concentration of 500 g/L. Purification of the synthesized oligosaccharides in the reaction mixture was done by fermentation with Kluyveromyces lactis CICC 1773 to remove the carbohydrate by-products, and HPLC on an oligosaccharide column. The purified oligosaccharides, namely, Oligo-1, Oligo-2, and Oligo-3 were determined for their monosaccharide components to be galactose and glucose in the molar ratios of 0.230:0.770, 0.522:0.478 and 0.637:0.363, respectively. These three oligosaccharides had relative molecular masses of 666.18, 990.26, and 1314.43, corresponding to the degree of polymerization (DP) value of 4, DP6, and DP8, respectively. NMR spectroscopic studies of the oligosaccharides revealed a common branched structure consisting of three glucosides, one of which was linked with one (Oligo-1), three (Oligo-2) and five galactosides (Oligo-3), respectively. These lactose-derived oligosaccharides with the structural patterns that were not reported earlier represented novel potential prebiotic agents for use in functional foods.
[Display omitted]
•Novel lactose-derived oligosaccharides (DP 4, 6, and 8) were synthesized by a two-step enzymatic method.•Inulosucrase gene from Lactobacillus gasseri DSM 20604 was expressed in Escherichia coli BL21(DE3).•Purification of oligosaccharides was done by yeast fermentation to remove carbohydrate by-products and HPLC.•The synthesized oligosaccharides with a specific branched structure were not reported earlier. Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research interests. In this study, a strategy of two-step enzymatic reactions was designed to first synthesize galacto-oligosaccharide (GOS) from lactose by β-galactosidase, and then the novel oligosaccharides were synthesized by inulosucrase (IS) using the obtained GOS and sucrose as the substrates. The recombinant IS was initially expressed by employing the IS gene from Lactobacillus gasseri DSM 20604. The appropriate synthesis conditions by the IS were determined as: reaction time of 12 h, the concentration of IS at 25 U/mL, GOS to sucrose ratio of 1:2, and the total substrate concentration of 500 g/L. Purification of the synthesized oligosaccharides in the reaction mixture was done by fermentation with Kluyveromyces lactis CICC 1773 to remove the carbohydrate by-products, and HPLC on an oligosaccharide column. The purified oligosaccharides, namely, Oligo-1, Oligo-2, and Oligo-3 were determined for their monosaccharide components to be galactose and glucose in the molar ratios of 0.230:0.770, 0.522:0.478 and 0.637:0.363, respectively. These three oligosaccharides had relative molecular masses of 666.18, 990.26, and 1314.43, corresponding to the degree of polymerization (DP) value of 4, DP6, and DP8, respectively. NMR spectroscopic studies of the oligosaccharides revealed a common branched structure consisting of three glucosides, one of which was linked with one (Oligo-1), three (Oligo-2) and five galactosides (Oligo-3), respectively. These lactose-derived oligosaccharides with the structural patterns that were not reported earlier represented novel potential prebiotic agents for use in functional foods.Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research interests. In this study, a strategy of two-step enzymatic reactions was designed to first synthesize galacto-oligosaccharide (GOS) from lactose by β-galactosidase, and then the novel oligosaccharides were synthesized by inulosucrase (IS) using the obtained GOS and sucrose as the substrates. The recombinant IS was initially expressed by employing the IS gene from Lactobacillus gasseri DSM 20604. The appropriate synthesis conditions by the IS were determined as: reaction time of 12 h, the concentration of IS at 25 U/mL, GOS to sucrose ratio of 1:2, and the total substrate concentration of 500 g/L. Purification of the synthesized oligosaccharides in the reaction mixture was done by fermentation with Kluyveromyces lactis CICC 1773 to remove the carbohydrate by-products, and HPLC on an oligosaccharide column. The purified oligosaccharides, namely, Oligo-1, Oligo-2, and Oligo-3 were determined for their monosaccharide components to be galactose and glucose in the molar ratios of 0.230:0.770, 0.522:0.478 and 0.637:0.363, respectively. These three oligosaccharides had relative molecular masses of 666.18, 990.26, and 1314.43, corresponding to the degree of polymerization (DP) value of 4, DP6, and DP8, respectively. NMR spectroscopic studies of the oligosaccharides revealed a common branched structure consisting of three glucosides, one of which was linked with one (Oligo-1), three (Oligo-2) and five galactosides (Oligo-3), respectively. These lactose-derived oligosaccharides with the structural patterns that were not reported earlier represented novel potential prebiotic agents for use in functional foods. Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research interests. In this study, a strategy of two-step enzymatic reactions was designed to first synthesize galacto-oligosaccharide (GOS) from lactose by β-galactosidase, and then the novel oligosaccharides were synthesized by inulosucrase (IS) using the obtained GOS and sucrose as the substrates. The recombinant IS was initially expressed by employing the IS gene from Lactobacillus gasseri DSM 20604. The appropriate synthesis conditions by the IS were determined as: reaction time of 12 h, the concentration of IS at 25 U/mL, GOS to sucrose ratio of 1:2, and the total substrate concentration of 500 g/L. Purification of the synthesized oligosaccharides in the reaction mixture was done by fermentation with Kluyveromyces lactis CICC 1773 to remove the carbohydrate by-products, and HPLC on an oligosaccharide column. The purified oligosaccharides, namely, Oligo-1, Oligo-2, and Oligo-3 were determined for their monosaccharide components to be galactose and glucose in the molar ratios of 0.230:0.770, 0.522:0.478 and 0.637:0.363, respectively. These three oligosaccharides had relative molecular masses of 666.18, 990.26, and 1314.43, corresponding to the degree of polymerization (DP) value of 4, DP6, and DP8, respectively. NMR spectroscopic studies of the oligosaccharides revealed a common branched structure consisting of three glucosides, one of which was linked with one (Oligo-1), three (Oligo-2) and five galactosides (Oligo-3), respectively. These lactose-derived oligosaccharides with the structural patterns that were not reported earlier represented novel potential prebiotic agents for use in functional foods. Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research interests. In this study, a strategy of two-step enzymatic reactions was designed to first synthesize galacto-oligosaccharide (GOS) from lactose by β-galactosidase, and then the novel oligosaccharides were synthesized by inulosucrase (IS) using the obtained GOS and sucrose as the substrates. The recombinant IS was initially expressed by employing the IS gene from Lactobacillus gasseri DSM 20604. The appropriate synthesis conditions by the IS were determined as: reaction time of 12 h, the concentration of IS at 25 U/mL, GOS to sucrose ratio of 1:2, and the total substrate concentration of 500 g/L. Purification of the synthesized oligosaccharides in the reaction mixture was done by fermentation with Kluyveromyces lactis CICC 1773 to remove the carbohydrate by-products, and HPLC on an oligosaccharide column. The purified oligosaccharides, namely, Oligo-1, Oligo-2, and Oligo-3 were determined for their monosaccharide components to be galactose and glucose in the molar ratios of 0.230:0.770, 0.522:0.478 and 0.637:0.363, respectively. These three oligosaccharides had relative molecular masses of 666.18, 990.26, and 1314.43, corresponding to the degree of polymerization (DP) value of 4, DP6, and DP8, respectively. NMR spectroscopic studies of the oligosaccharides revealed a common branched structure consisting of three glucosides, one of which was linked with one (Oligo-1), three (Oligo-2) and five galactosides (Oligo-3), respectively. These lactose-derived oligosaccharides with the structural patterns that were not reported earlier represented novel potential prebiotic agents for use in functional foods. |
| ArticleNumber | 116177 |
| Author | Aziz, Tariq Sarwar, Abid Yang, Zhennai Alasmari, Abdullah F. Hu, Gege Ren, Qingxia Hu, Hangyu Yang, Zhang Zhang, Min |
| Author_xml | – sequence: 1 givenname: Hangyu surname: Hu fullname: Hu, Hangyu organization: Key Laboratory of Geriatric Nutrition and Health of Ministry of Education, Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Engineering and Technology Research Center of Food Additives, Beijing Technology and Business University, 100048, Beijing, China – sequence: 2 givenname: Gege surname: Hu fullname: Hu, Gege organization: Key Laboratory of Geriatric Nutrition and Health of Ministry of Education, Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Engineering and Technology Research Center of Food Additives, Beijing Technology and Business University, 100048, Beijing, China – sequence: 3 givenname: Min surname: Zhang fullname: Zhang, Min organization: Key Laboratory of Agro-Products Primary Processing, Academy of Agricultural Planning and Engineering, MARA, Beijing 100125, China – sequence: 4 givenname: Qingxia surname: Ren fullname: Ren, Qingxia organization: Key Laboratory of Geriatric Nutrition and Health of Ministry of Education, Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Engineering and Technology Research Center of Food Additives, Beijing Technology and Business University, 100048, Beijing, China – sequence: 5 givenname: Tariq surname: Aziz fullname: Aziz, Tariq organization: Key Laboratory of Geriatric Nutrition and Health of Ministry of Education, Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Engineering and Technology Research Center of Food Additives, Beijing Technology and Business University, 100048, Beijing, China – sequence: 6 givenname: Abid surname: Sarwar fullname: Sarwar, Abid organization: Key Laboratory of Geriatric Nutrition and Health of Ministry of Education, Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Engineering and Technology Research Center of Food Additives, Beijing Technology and Business University, 100048, Beijing, China – sequence: 7 givenname: Abdullah F. surname: Alasmari fullname: Alasmari, Abdullah F. organization: Department of Pharmacology and Toxicology, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia – sequence: 8 givenname: Zhennai surname: Yang fullname: Yang, Zhennai email: yangzhennai@th.btbu.edu.cn organization: Key Laboratory of Geriatric Nutrition and Health of Ministry of Education, Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Engineering and Technology Research Center of Food Additives, Beijing Technology and Business University, 100048, Beijing, China – sequence: 9 givenname: Zhang surname: Yang fullname: Yang, Zhang email: zhangyang@gmc.edu.cn organization: Department of Neurology, Affiliated Hospital of Guizhou Medical University, Guiyang 55005, China |
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| Keywords | Sucrose DMSO LS HH-COSY DP TFA Transfructosylation MFOS ESI β-Galactosidase HPLC GC–MS Isomerization HMBC GOS IS Oligosaccharides FOS NEA SDS-PAGE Lactose NMR Inulosucrase IPTG PMAA UPLC-MS/MS GRAS HSQC LFOS RFOS |
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| Snippet | Exploitation of the added value of lactose by enzymatic synthesis of novel lactose-derived oligosaccharides has been a subject of increasing research... |
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| SubjectTerms | beta-Galactosidase - metabolism Fermentation food research galactose Galactose - metabolism galactosides genes glucose glucosides Inulosucrase Isomerization Kluyveromyces - metabolism Kluyveromyces marxianus var. lactis Lactobacillus - enzymology Lactobacillus - genetics Lactobacillus gasseri Lactose Lactose - chemistry Lactose - metabolism Oligosaccharides Oligosaccharides - biosynthesis Oligosaccharides - chemical synthesis Oligosaccharides - chemistry polymerization Prebiotics spectroscopy Sucrose Sucrose - metabolism Transfructosylation β-Galactosidase |
| Title | Synthesis of novel lactose-derived oligosaccharides by two-step enzymatic reactions and structural characterization of the oligomers |
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