Synthesis of CH₂-Linked Isomaltose via α-Selective Photoredox Vinyl C-Glycosylation
Abstract
C-Glycoside analogs of bioactive glycans and glycoconjugates are resistant to glycosidic hydrolysis and thus represent valuable scaffolds for drug discovery and chemical biology. We previously found that CH2-linked isomaltose (CH2-IM) exhibits potent amylase-inducing activity in Aspergillus nidulans compared to its native and linkage-edited counterparts. Here, we report a streamlined synthesis of CH2-IM via photoredox-catalyzed vinyl-C-glycosylation using N,N-dialkylbenzylamine derivatives as efficient halogen-atom transfer reagents. This approach enables concise access to CH2-IM and also facilitates the synthesis of 6′-modified analogs, providing a versatile platform for probing structure–activity relationships of IM derivatives. Notably, functionalization at the 6′- and anomeric positions completely abolishes the amylase induction activity.
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BibTeX
@article{tanabe2026synthesis,
title = {{Synthesis of CH₂-Linked Isomaltose via α-Selective Photoredox Vinyl C-Glycosylation}},
author = {Riko Tanabe and Makoto Yoritate and Minori Numamoto and Li Rui and Takahiro Moriyama and Noriaki Kiya and Hiroaki Matoba and Naoki Kato and Go Hirai},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2026},
month = aug,
doi = {10.1248/cpb.c26-00382},
url = {https://www.jstage.jst.go.jp/article/cpb/74/8/74_c26-00382/_article},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Synthesis of CH₂-Linked Isomaltose via α-Selective Photoredox Vinyl C-Glycosylation
AU - Riko Tanabe
AU - Makoto Yoritate
AU - Minori Numamoto
AU - Li Rui
AU - Takahiro Moriyama
AU - Noriaki Kiya
AU - Hiroaki Matoba
AU - Naoki Kato
AU - Go Hirai
PY - 2026
DA - 2026/08/27
JO - Chemical and Pharmaceutical Bulletin
DO - 10.1248/cpb.c26-00382
UR - https://www.jstage.jst.go.jp/article/cpb/74/8/74_c26-00382/_article
AB - C-Glycoside analogs of bioactive glycans and glycoconjugates are resistant to glycosidic hydrolysis and thus represent valuable scaffolds for drug discovery and chemical biology. We previously found that CH2-linked isomaltose (CH2-IM) exhibits potent amylase-inducing activity in Aspergillus nidulans compared to its native and linkage-edited counterparts. Here, we report a streamlined synthesis of CH2-IM via photoredox-catalyzed vinyl-C-glycosylation using N,N-dialkylbenzylamine derivatives as efficient halogen-atom transfer reagents. This approach enables concise access to CH2-IM and also facilitates the synthesis of 6′-modified analogs, providing a versatile platform for probing structure–activity relationships of IM derivatives. Notably, functionalization at the 6′- and anomeric positions completely abolishes the amylase induction activity.
SN - 1347-5223
SN - 0009-2363
ER -