| Project/Area Number |
61303011
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| Research Category |
Grant-in-Aid for Co-operative Research (A)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Tottori University |
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Principal Investigator |
SHIGEMASA Yoshihiro Department of Industrial Chemistry, Faculty of Engineering, Tottori University, 工学部, 教授 (00032029)
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| Co-Investigator(Kenkyū-buntansha) |
NAKASIMA Ruka Department of Industrial Chemistry, Faculty of Engineering, Tottori University, 工学部, 教授 (40025987)
MATUURA Teruo Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University, 工学部, 教授 (90025809)
SAKAI Tomoya Department of Chemical Reaction Engineering, Faculty of Pharmaceutical Science,, 薬学部, 教授 (00080169)
YOSHIKAWA Sadao Department of Applied Chemistry, Faculty of Science and Technology, Keio Univers, 理工学部, 教授 (70010759)
UCHIDA Yasuzo Department of Synthetic Chemistry, Faculty of Engineering, Tokyo University, 工学部, 教授 (00010752)
井上 祥平 東京大学, 工学部, 教授 (20010762)
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| Project Period (FY) |
1986 – 1988
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| Project Status |
Completed (Fiscal Year 1988)
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| Budget Amount *help |
¥10,400,000 (Direct Cost: ¥10,400,000)
Fiscal Year 1988: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1987: ¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 1986: ¥6,000,000 (Direct Cost: ¥6,000,000)
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| Keywords | formaldehyde / formose / non-natural sugar / thiazolium salt / 2-hydroxymethyl-3-pentulose / エピメリ化 / 金属錯体 / ジヒドロキシアセトン / グリセロテトルロース / 糖質 / カニツアロ反応 / チアゾリウム / 溶媒効果 |
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| Research Abstract |
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.
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