Synthesis of Formose and Application

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1. In the formose reaction catalyzed by 2-(dimethylamino)ethanol and thiamin hydrochloride in N,N-dimethylformamide (DMF), dihydroxyacetone and DL-glycero-tetrulose were formed selectively at the formaldehyde concentration of 1.1 M and 3.0 M, respectively. Furthermore, the favored formation of 2,4- bis(hydroxymethyl)-3-&entulose(2,4-BH-3-p) or 2-hydroxymethyl-3-pentulose(2-H-3-P) which was a precursor of 2,4-BH-3-P, was obtained by regulating the fraction of water in DMF. Those products were also isolated from formose.2. A new carbon-chain lengthening method in carbohydrate synthesis of applying a selective acyloin condensation with triethylamine and 3-ethyl-bromobenzothiazolium(EBB) in ethanol was found to give d-fructose from 1,2,3,4-tetra-0-acetyl-D-arabinose and formaldehyde in a good yield. The formose reaction, furthermore, was carried out under the irradiation of Co-60 -ray to an aqueous formaldehyde solution in the presence of various inorganic bases. The effects of the formaldehyde concentration on products were also investigated.3. polyhydroxymethylated compounds of acetone were synthesized selectively from formaldehyde and various metal-acetylacetone complexes. Isomerization of sugars catalyzed by various metal-diamine complexes was studied. Ni^<2+>, Co^<2+>, Ca^<2+> and Sr^<2+> catalyzed effectively the epimerization at C-2 of aldoses. In the case of Ca^<2+>, fructose was formed besides the C-2 epimer.4. When formose will be used biologically, it might be predicted that non-natural sugars would affect vital functions. From these point of view, the decomposition and synthesis of non-natural sugars with various microorganizms were studied and their mechanisms were proposed.5. Analytical process of formose with enzymes, oxidation of sugars, and some approaches for synthesis of sugars have also been investigated.