Synthesis of CH₂-Linked Isomaltose via α-Selective Photoredox Vinyl C-Glycosylation.

Authors

Riko Tanabe, Makoto Yoritate, Minori Numamoto, Li Rui, Takahiro Moriyama, Noriaki Kiya, Hiroaki Matoba, Naoki Kato, Go Hirai

Published in

Chemical & pharmaceutical bulletin. Volume 74. Issue 8. Pages 651-654.

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.

PMID:
42649024
Bibliographic data and abstract were imported from PubMed on 27 Aug 2026.

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