Stereoselective Total Synthesis of α-Galacto-Oligosaccharides Using Boron-Mediated Aglycon Delivery and Evaluation of their Immune-Enhancing Activities.

Jikun Meng, Moeri Sagawa, Kazunobu Toshima, Daisuke Takahashi

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Article in Chembiochem : a European journal of chemical biology, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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4 authors.

Jikun MengDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.

Moeri SagawaDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.

Kazunobu ToshimaDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.ORCID http://orcid.org/0000-0003-3994-9099

Daisuke TakahashiDepartment of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.ORCID http://orcid.org/0000-0003-3222-6648

Funding

Core Research for Evolutional Science and Technology JPMJCR20R3Japan Agency for Medical Research and Development JP22gm1610010Japan Science and Technology Agency JPMJSP2123Japan Society for the Promotion of Science JP23H01966

6 · The paper itself

Abstract

α-Galacto-oligosaccharides (α-GOSs) are natural oligomeric saccharides found in plants that have garnered significant interest due to their indigestible nature and various biological activities. However, they often exist as inseparable mixtures, particularly long-chain substances. This study successfully achieves the total synthesis of α-GOSs 1-6, featuring different lengths of galactose chains, using the boron-mediated aglycon delivery method developed in our laboratory. Additionally, this study investigates the immune-enhancing activity and structure-activity relationships of the chemically synthesized α-GOSs. It reveals that the length of the galactose chain in the α-GOSs significantly influences their immune-enhancing properties. Specifically, α-GOS 2, which contains two galactose units, is found to markedly promote macrophage phagocytosis and increase the production of cytokines such as IL-6, TNF-α, and IL-1β. These results suggest that α-GOS 2 could serve as a natural immunomodulatory agent in functional foods.

Indexed as

BoronGalactoseOligosaccharidesAnimalsCytokinesMacrophagesMicePhagocytosisRAW 264.7 CellsStereoisomerismStructure-Activity RelationshipBoronCytokinesGalactoseOligosaccharidesboron‐mediated aglycon deliveryimmune‐enhancing activityα‐galacto‐oligosaccharides

Identifiers

PMID40193240

DOI10.1002/cbic.202401059

PMCPMC12135125

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