Screening of biologically active monosaccharides: growth inhibitory effects of d-allose, d-talose, and l-idose against the nematode <i>Caenorhabditis elegans</i>

<p>We compared the growth inhibitory effects of all aldohexose stereoisomers against the model animal <i>Caenorhabditis elegans</i>. Among the tested compounds, the rare sugars d-allose (d-All), d-talose (d-Tal), and l-idose (l-Ido) showed considerable growth inhibition under both monoxenic and axenic culture conditions<i>.</i> 6-Deoxy-d-All had no effect on growth, which suggests that C6-phosphorylation by hexokinase is essential for inhibition by d-All.</p

Triacetonide of Glucoheptonic Acid in the Scalable Syntheses of d‑Gulose, 6‑Deoxy‑d‑gulose, l‑Glucose, 6‑Deoxy‑l‑glucose, and Related Sugars

Ease of separation of petrol-soluble acetonides derived from the triacetonide of methyl glucoheptonate allows scalable syntheses of rare sugars containing the l-gluco or d-gulo structural motif with any oxidation level at the C6 or C1 position of the hexose, usually without chromatography: <i>meso</i>-d-glycero-d-guloheptitol available in two steps is an ideal entry point for the study of the biotechnological production of heptoses

General Synthesis of Sugar-Derived Azepane Nitrones: Precursors of Azepane Iminosugars

A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars

Eight Stereoisomers of Homonojirimycin from d-Mannose

Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ

Synthesis from d‑Altrose of (5<i>R</i>,6<i>R</i>,7<i>R</i>,8<i>S</i>)‑5,7-Dihydroxy-8-hydroxymethylconidine and 2,4-Dideoxy-2,4-imino‑d‑glucitol, Azetidine Analogues of Swainsonine and 1,4-Dideoxy-1,4-imino‑d‑mannitol

Ring closure of a 3,5-di-<i>O</i>-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine