Molecular Basis of Absorption at 340 nm of 3-Ketoglucosides under Alkaline Conditions

Motomitsu Kitaoka; Ayu Takano; Mei Takahashi; Yoshiki Yamakawa; Shinya Fushinobu; Nobuyuki Yoshida

doi:10.5458/jag.jag.JAG-2023_0014

Regular Papers

Molecular Basis of Absorption at 340 nm of 3-Ketoglucosides under Alkaline Conditions

Motomitsu Kitaoka , Ayu Takano, Mei Takahashi, Yoshiki Yamakawa, Shinya Fushinobu, Nobuyuki Yoshida

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Keywords: 3-ketoglucoside, alkaline treatment, 3-ketolevoglucosan, 2-hydroxy-3-ketoglucal, Absorption at 340 nm

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Supplementary material

2024 Volume 71 Issue 1 Pages 9-13

DOI https://doi.org/10.5458/jag.jag.JAG-2023_0014

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Abstract

Transient absorption at 340 nm under alkaline conditions has long been used to detect the presence of 3-keto-O-glycosides without understanding the molecular basis of the absorbance. The time course of A_{340 nm} for the alkaline treatment of 3-ketolevoglucosan, an intramolecular 3-keto-O-glycoside, was investigated to identify the three products generated through alkaline treatment. By comparing the spectra of these compounds under neutral and alkaline conditions, we identified 1,5-anhydro-D-erythro-hex-1-en-3-ulose (2-hydroxy-3-keto-D-glucal) as being the compound responsible for the absorption.

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