title: Development of a chemical strategy to produce rare aldohexoses from ketohexoses using 2-aminopyridine.
abstract: Rare sugars are monosaccharides that are found in relatively low abundance in nature. Herein, we describe a strategy for producing rare aldohexoses from ketohexoses using the classical Lobry de Bruyn-Alberda van Ekenstein transformation. Upon Schiff-base formation of keto sugars, a fluorescence-labeling reagent, 2-aminopyridine (2-AP), was used. While acting as a base catalyst, 2-AP efficiently promoted the ketose-to-aldose transformation, and acting as a Schiff-base reagent, it effectively froze the ketose-aldose equilibrium. We could also separate a mixture of Sor, Gul, and Ido in their Schiff-base forms using a normal-phase HPLC separation system. Although Gul and Ido represent the most unstable aldohexoses, our method provides a practical way to rapidly obtain these rare aldohexoses as needed.
authors: Department of Functional Glycomics, Life Science Research Center, Kagawa University, 1750-1 Ikenobe, Miki-cho, Kita-gun, Kagawa 761-0793, Japan.
authors: Kayo
authors: K
authors: Hasehira
authors: Nobumitsu
authors: N
authors: Miyanishi
authors: Wataru
authors: W
authors: Sumiyoshi
authors: Jun
authors: J
authors: Hirabayashi
authors: Shin-ichi
authors: S
authors: Nakakita
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000302:isolation & purification; D000631:Aminopyridines / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D006601:Hexoses / Q000138:chemical synthesis* / Q000302:isolation & purification; D006868:Hydrolysis; D007661:Ketoses / Q000138:chemical synthesis* / Q000302:isolation & purification; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D014269:Trifluoroacetic Acid / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000631:Aminopyridines; D006601:Hexoses; D007661:Ketoses; D012545:Schiff Bases; D014269:Trifluoroacetic Acid; C032439:alpha-aminopyridine