Abstract
This paper presents a study on a series of quaternary ammonium salt (QAS) derivatives of glucopyranosides with an elongated hydrophobic hydrocarbon chain. The new N-[6-(β-D-glucopyranosyloxy)hexyl]ammonium bromides and their O-acetyl derivatives were analyzed via 1H and 13C NMR spectroscopy. The mutagenic activity of the newly synthesized QAS was investigated using two different techniques: The Vibrio harveyi luminescence assay and the Ames test. The obtained results support previous findings contesting QAS safety and indicate that QAS, specifically pyridinium derivatives, might be mutagenic.
Highlights
Carbohydrates and alditols occur broadly in nature and possess many biological functions essential to living organisms
We synthesized N-[6-(β-D-glucopyranosyloxy)hexyl]ammonium salts to determine the effect of the linker length in quaternary ammonium salt (QAS) on their mutagenic potential (Scheme 1)
Since de-O-acetylated salts could not be obtained using sodium methanolate in methanol, an alternative route involving the reaction of 6-bromohexyl D-glucopyranoside (2′ [32] or 3′) with tertiary amines was applied; the yields were of 90–94%
Summary
Carbohydrates and alditols occur broadly in nature and possess many biological functions essential to living organisms. Quaternary ammonium salts (QASs) constitute a class of organic compounds with a broad range of applications. We describe process of synthesis, structural characteristics, and mutagenic activity profile of eight new QAS derivatives of 6-aminohexyl D-glucopyranosides.
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