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효소를 이용한 Cyclic Meso-dicarboxylic acid anhydride의 고리열림 반응
안용현,이승준 단국대학교 1998 論文集 Vol.33 No.-
By using the enzyme, we have tried the ring opening of cyclic acid anhydride which is the intermediate in the synthesis of (+)biotin. Lipase PS, lipase AK, lipase AY, porcine liver esterase, lipase AP12, lipase M10, prozyme 6 and lipase M were used as enzymes and methanol, npropanol, noctanol and (-)menthol were applied as a nucleophile. In the absence of enzyme, reaction with nbutanol was proved to proceed less then 1%. The reaction progress was fast when the enzyme was used, but the optical purity of monoester was very poor. When the lipase AK and nbutanol were applied, the optical purity of monoester was 705%ee. However, (-)menthol was used under the same condition, the optical rotation was opposite and optical purity was 11.2%ee.
Chromobacterium chocolatum에서의 lipase유전자분리 및 발현
안용현,장지명 단국대학교 2000 論文集 Vol.35 No.-
A kind of vitamin B group. (+)-biotin has been known to have an influence on the growth of an organism and used for feeding material. Biotin has been synthesized by chemical method, and then crystallized with d-ephedrine to get the optically pure form. Lipase have been used for the resolution of chiral compound from racemic mixture. One of intermediates in the biotin synthesis is a diester which is a meso compound. Chromobacterium chocolatum has applied to hydrolyze one methyl ester group. The mono ester was successfully used for the synthesis of (+)-biotin as well as high optical purity. The goal of this research is the genetic cloning of lipase which hydrolyze the dimethyl ester from Chromobacterium chocolatum and identify its enzymatic reaction.
Synthesis of 2-Aryl-5,6,7,8-tetrahydro-3-cinnolinones
안용현,이윤영,Yong Hyun Ahn,Youn Young Lee Korean Chemical Society 1985 대한화학회지 Vol.29 No.1
2-치환 5,6,7,8-테트라히드로-3-신놀린온 합성에 이용할 2-(2,2,2-트리클로로에틸리덴) 시클로헥산온(1)을 시클로헥산온과 클로랄의 엔아민축합으로 얻고자 하였다. 그러나 1-모르폴리노-1-시클로헥센(2)과 클로랄을 축합한 결과 2-(1-히드록시-2,2,2-트리클로로에틸)시클로헥산온(3)이 생성되었으며, 이것을 탈수시킨 결과 2-(2,2-디클로로비닐)-2-시클로헥센온(4)이 얻어졌다. 화합물 1대신에 ${\alpha}$-(4-모로폴린일)-${\alpha}$-(2-옥소시클로헥실)아세트산 모르폴린일륨(5)을 사용하여 아릴 하드라진들과 반응시킴으로써 2-아릴-5,6,7,8-테트라히드로-3-신놀린올들을 합성할 수 있었다. The preparation of 2-(2,2,2-trichloroethylidene)cyclohexanone(1), as a key compound for synthesizing 2-substituted 5,6,7,8-tetrahydro-3-cinnolinones, was attempted by the enamine condensation of cyclohexanone with chloral. However, the condensation of 1-morpholino-1-cyclohexene (2) with chloral afforded 2-(1-hydroxy-2,2,2-trichloroethyl) cyclohexanone (3), and its dehydration led to 2-(2,2-dichlorovinyl)-2-cyclohexenone (4). 2-Aryl-5,6,7,8-tetrahydro-3-cinnolinones could be synthesized using morpholinium ${\alpha}$-(4-morpholinyl)-${\alpha}$-(2-oxocyclohexyl)-acetate (5) in place of 1 with arylhydrazines.