α-Selective Glycosidation of the Rare Sugar D-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide

Makura, Yui; Iyoshi, Akihiro; Horiuchi, Makito; Hu, Yiming; Tanaka, Masakazu; Ueda, Atsushi

doi:10.3390/ijms26178459

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α-Selective Glycosidation of the Rare Sugar D-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide

by

Yui Makura

¹,

Akihiro Iyoshi

¹,

Makito Horiuchi

²,

Yiming Hu

¹,

Masakazu Tanaka

¹ and

Atsushi Ueda

^1,*

¹

Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

²

School of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

^*

Author to whom correspondence should be addressed.

Int. J. Mol. Sci. 2025, 26(17), 8459; https://doi.org/10.3390/ijms26178459 (registering DOI)

Submission received: 31 July 2025 / Revised: 22 August 2025 / Accepted: 29 August 2025 / Published: 30 August 2025

(This article belongs to the Special Issue Heterocyclic Compounds: Synthesis, Design, and Biological Activity)

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Abstract

<sc>d</sc>-Tagatose is a rare sugar that exhibits intriguing biological properties, such as its role as a low-calorie sweetener and its ability to reduce the glycemic response. Consequently, the synthesis of <sc>d</sc>-tagatose derivatives is a crucial endeavor for the advancement of their functionalities, as well as elucidation of their biological properties. In this study, we present the α-selective glycosidation of a 1,3,4,6-tetra-O-benzoylated <sc>d</sc>-tagatofuranosyl donor with various glycosyl acceptors. In contrast to <sc>d</sc>-allulose, which is the C3,C4-epimer of <sc>d</sc>-tagatose and does not exhibit the neighboring group effect, the current <sc>d</sc>-tagatofuranosyl donor demonstrated significant neighboring group participation, achieving high α-selectivity ratios up to α:β = 99:1. This method was also applicable to the synthesis of α-<sc>d</sc>-tagatofuranosylceramide, which has potential as a novel functional molecule. Meanwhile, the glycosylation of sterically congested glycosyl acceptors, such as 2-hydroxycumene, resulted in poor α-selectivity, which may be attributed to the interaction with the C1-benzoyloxy group of <sc>d</sc>-tagatofuranosyl donors in the transition state.

Keywords: dtagatose; rare sugar; α-selective glycosidation; regioselective protection; furanosyl donor; glycosylceramide; cerebroside

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MDPI and ACS Style

Makura, Y.; Iyoshi, A.; Horiuchi, M.; Hu, Y.; Tanaka, M.; Ueda, A. α-Selective Glycosidation of the Rare Sugar D-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide. Int. J. Mol. Sci. 2025, 26, 8459. https://doi.org/10.3390/ijms26178459

AMA Style

Makura Y, Iyoshi A, Horiuchi M, Hu Y, Tanaka M, Ueda A. α-Selective Glycosidation of the Rare Sugar D-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide. International Journal of Molecular Sciences. 2025; 26(17):8459. https://doi.org/10.3390/ijms26178459

Chicago/Turabian Style

Makura, Yui, Akihiro Iyoshi, Makito Horiuchi, Yiming Hu, Masakazu Tanaka, and Atsushi Ueda. 2025. "α-Selective Glycosidation of the Rare Sugar D-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide" International Journal of Molecular Sciences 26, no. 17: 8459. https://doi.org/10.3390/ijms26178459

APA Style

Makura, Y., Iyoshi, A., Horiuchi, M., Hu, Y., Tanaka, M., & Ueda, A. (2025). α-Selective Glycosidation of the Rare Sugar D-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide. International Journal of Molecular Sciences, 26(17), 8459. https://doi.org/10.3390/ijms26178459

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α-Selective Glycosidation of the Rare Sugar D-Tagatofuranose and the Synthesis of α-d-Tagatofuranosylceramide

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